9 days
Contact us for pricing.
Contact us for pricing.
Boston
»
Newport
»
Block Island
»
Martha's Vineyard
»
Nantucket
»
Hadley Harbor
9 days
Contact us for pricing.
Contact us for pricing.
Boston
»
Newport
»
Block Island
»
Martha's Vineyard
»
Nantucket
»
Hadley Harbor
Call Us on
Call Us on
Monday - Friday 9.30am - 5pm
Monday - Friday 9.30am - 5pm
Envision Yourself in this Enchanting Escape
Envision Yourself in this
Enchanting Escape
Envision Yourself in this Enchanting Escape
New England Charm on a Luxury Yacht
New England Charm on a Luxury Yacht
Discover the allure of the New England region like never before, as you set sail on a luxury yacht that promises both comfort and adventure. Your voyage will lead you to iconic destinations such as Boston, Newport, Block Island, Martha's Vineyard, Nantucket, and Hadley Harbor, each brimming with its own unique charm. Indulge in the captivating ambiance of picturesque villages and treat your taste buds to the gastronomic wonders of Martha's Vineyard. Delight in a personalized wine and oyster tasting experience guided by an expert.
Embark on a journey through nature along the captivating U.S. East Coast, where you'll trek through remote trails offering breathtaking views of rugged coastlines and untouched landscapes. Find tranquility on the pristine sandy shores of Block Island, where you can unwind and soak in the sun's warm embrace.
Elevate your escapade by making the luxurious yacht your home, complete with a dedicated crew to cater to your every need. This promises to be an adventure of a lifetime, where New England's charm and the opulence of a yacht converge into an unforgettable experience.
Discover the allure of the New England region like never before, as you set sail on a luxury yacht that promises both comfort and adventure. Your voyage will lead you to iconic destinations such as Boston, Newport, Block Island, Martha's Vineyard, Nantucket, and Hadley Harbor, each brimming with its own unique charm. Indulge in the captivating ambiance of picturesque villages and treat your taste buds to the gastronomic wonders of Martha's Vineyard. Delight in a personalized wine and oyster tasting experience guided by an expert.
Embark on a journey through nature along the captivating U.S. East Coast, where you'll trek through remote trails offering breathtaking views of rugged coastlines and untouched landscapes. Find tranquility on the pristine sandy shores of Block Island, where you can unwind and soak in the sun's warm embrace.
Elevate your escapade by making the luxurious yacht your home, complete with a dedicated crew to cater to your every need. This promises to be an adventure of a lifetime, where New England's charm and the opulence of a yacht converge into an unforgettable experience.
why this journey works
New England's best harbors — Newport, Block Island, Martha's Vineyard, Nantucket, Hadley Harbor — were built to be arrived at by water, and this itinerary treats the crewed Milestone motor yacht as the trip's actual home. A Boston night at the Four Seasons opens the route before you board. We like how the middle days repeat islands without repeating experiences: sandy leisure on Block Island, food-led time and a guided wine-and-oyster tasting on Martha's Vineyard, coastal trails around Nantucket. The crew handles everything in between.
Typical Trip Investment
Typical Trip Investment
Typical Trip Investment
Pricing for this journey depends on your dates, the season, and how you want to travel.
Inspirational Itinerary
Inspirational Itinerary
Inspirational Itinerary
Consider this itinerary a springboard for your dream vacation. You can either adopt it as presented or use elements you love from it.
Consider this itinerary a springboard for your dream vacation. You can either adopt it as presented or use elements you love from it.
Personalized Experience
Personalized Experience
Personalized Experience
We’re dedicated to customizing this journey to match your preferences and travel style, ensuring a unique and unforgettable adventure.
We’re dedicated to customizing this journey to match your preferences and travel style, ensuring a unique and unforgettable adventure.
why this journey works
New England's best harbors — Newport, Block Island, Martha's Vineyard, Nantucket, Hadley Harbor — were built to be arrived at by water, and this itinerary treats the crewed Milestone motor yacht as the trip's actual home. A Boston night at the Four Seasons opens the route before you board. We like how the middle days repeat islands without repeating experiences: sandy leisure on Block Island, food-led time and a guided wine-and-oyster tasting on Martha's Vineyard, coastal trails around Nantucket. The crew handles everything in between.
New England Charm on a Luxury Yacht
01
Discover the Extraordinary
New England by Nature
New England by Nature
Discover the region that frames your yacht journey in this New England destination film.
Discover the region that frames your yacht journey in this New England destination film.
Watch the video
02
At a glance
Best for
Best for
Best for
Travelers who want New England's islands by private yacht with crewed comfort
travel style
travel style
travel style
Private yacht cruising, coastal New England, food and wine, island time
stays
stays
stays
Four Seasons Hotel Boston; Milestone Motor Yacht
highlights
highlights
highlights
Boston start at the Four Seasons
Newport, Block Island, and Hadley Harbor by yacht
Martha's Vineyard dining and island time
Guided wine and oyster tasting
Nantucket days with coastal trail walks
03
Imagine this
Immerse in your day-by-day itinerary
recommendation
Immerse in your
day-by-day itinerary recommendation
Day 1
Boston
Your Journey Begins
Upon your arrival at the airport, you'll have the opportunity to enjoy a VIP Meet & Greet service, allowing for a seamless and efficient transition to your private vehicle and chauffeur. From there, you will be personally transported to your chosen accommodations.
Embark on a captivating journey through history with a private guided tour, as you leisurely traverse Boston's famous 2.5-mile red line, which connects you to 16 nationally significant historic locations. This remarkable path, known as the Freedom Trail, was lovingly preserved and dedicated by the people of Boston in 1951. It showcases a unique collection of museums, churches, meeting houses, burial grounds, parks, a ship, and historic markers, all of which vividly narrate the story of the American Revolution and more. Today, the Freedom Trail stands as a globally renowned and iconic tourist attraction, drawing in over 4 million visitors annually to explore Boston's precious 17th, 18th, and 19th-century heritage sites.
To conclude your day, savor the convenience of pre-arranged dinner reservations at the restaurant of your preference.
Day 1
Boston
Your Journey Begins
Upon your arrival at the airport, you'll have the opportunity to enjoy a VIP Meet & Greet service, allowing for a seamless and efficient transition to your private vehicle and chauffeur. From there, you will be personally transported to your chosen accommodations.
Embark on a captivating journey through history with a private guided tour, as you leisurely traverse Boston's famous 2.5-mile red line, which connects you to 16 nationally significant historic locations. This remarkable path, known as the Freedom Trail, was lovingly preserved and dedicated by the people of Boston in 1951. It showcases a unique collection of museums, churches, meeting houses, burial grounds, parks, a ship, and historic markers, all of which vividly narrate the story of the American Revolution and more. Today, the Freedom Trail stands as a globally renowned and iconic tourist attraction, drawing in over 4 million visitors annually to explore Boston's precious 17th, 18th, and 19th-century heritage sites.
To conclude your day, savor the convenience of pre-arranged dinner reservations at the restaurant of your preference.
Day 1
Boston
Your Journey Begins
Upon your arrival at the airport, you'll have the opportunity to enjoy a VIP Meet & Greet service, allowing for a seamless and efficient transition to your private vehicle and chauffeur. From there, you will be personally transported to your chosen accommodations.
Embark on a captivating journey through history with a private guided tour, as you leisurely traverse Boston's famous 2.5-mile red line, which connects you to 16 nationally significant historic locations. This remarkable path, known as the Freedom Trail, was lovingly preserved and dedicated by the people of Boston in 1951. It showcases a unique collection of museums, churches, meeting houses, burial grounds, parks, a ship, and historic markers, all of which vividly narrate the story of the American Revolution and more. Today, the Freedom Trail stands as a globally renowned and iconic tourist attraction, drawing in over 4 million visitors annually to explore Boston's precious 17th, 18th, and 19th-century heritage sites.
To conclude your day, savor the convenience of pre-arranged dinner reservations at the restaurant of your preference.
Day 2
Boston to Newport
All aboard! It's time to embark on our journey!
Prepare for your journey as you meet your private driver, who will escort you on a scenic transfer to Newport. Anticipate an approximate travel time of one hour and 35 minutes.
Envision an exclusive experience with the option of a private tour before or after regular visiting hours at The Breakers, or perhaps a tour of Marble House, culminating in cocktails on the terrace and an exquisite dinner in the Gold Room. For the epitome of luxury, entrust your private guide to lead you on an extraordinary adventure not accessible to the general public.
Your extraordinary Luxe Yacht All-Inclusive Package encompasses a crewed charter rate, an Advanced Provision Allowance that covers fuel, all on-board culinary delights and beverages, designated dockage in accordance with your itinerary, inclusive taxes and fees, crew gratuity, 24/7 concierge service, personalized itinerary planning, and yacht provisioning. Your dedicated yacht crew will coordinate yacht toys, amenities, and activities, with each day allowing for up to five hours of cruising time.
Welcome aboard! Savor a welcoming glass of champagne as you acquaint yourself with your dedicated crew members, who will be at your beck and call throughout your charter. These knowledgeable crew members are committed to ensuring your voyage is a once-in-a-lifetime experience, tending to your every need and crafting the journey of your dreams.
Day 2
Boston to Newport
All aboard! It's time to embark on our journey!
Prepare for your journey as you meet your private driver, who will escort you on a scenic transfer to Newport. Anticipate an approximate travel time of one hour and 35 minutes.
Envision an exclusive experience with the option of a private tour before or after regular visiting hours at The Breakers, or perhaps a tour of Marble House, culminating in cocktails on the terrace and an exquisite dinner in the Gold Room. For the epitome of luxury, entrust your private guide to lead you on an extraordinary adventure not accessible to the general public.
Your extraordinary Luxe Yacht All-Inclusive Package encompasses a crewed charter rate, an Advanced Provision Allowance that covers fuel, all on-board culinary delights and beverages, designated dockage in accordance with your itinerary, inclusive taxes and fees, crew gratuity, 24/7 concierge service, personalized itinerary planning, and yacht provisioning. Your dedicated yacht crew will coordinate yacht toys, amenities, and activities, with each day allowing for up to five hours of cruising time.
Welcome aboard! Savor a welcoming glass of champagne as you acquaint yourself with your dedicated crew members, who will be at your beck and call throughout your charter. These knowledgeable crew members are committed to ensuring your voyage is a once-in-a-lifetime experience, tending to your every need and crafting the journey of your dreams.
Day 2
Boston to Newport
All aboard! It's time to embark on our journey!
Prepare for your journey as you meet your private driver, who will escort you on a scenic transfer to Newport. Anticipate an approximate travel time of one hour and 35 minutes.
Envision an exclusive experience with the option of a private tour before or after regular visiting hours at The Breakers, or perhaps a tour of Marble House, culminating in cocktails on the terrace and an exquisite dinner in the Gold Room. For the epitome of luxury, entrust your private guide to lead you on an extraordinary adventure not accessible to the general public.
Your extraordinary Luxe Yacht All-Inclusive Package encompasses a crewed charter rate, an Advanced Provision Allowance that covers fuel, all on-board culinary delights and beverages, designated dockage in accordance with your itinerary, inclusive taxes and fees, crew gratuity, 24/7 concierge service, personalized itinerary planning, and yacht provisioning. Your dedicated yacht crew will coordinate yacht toys, amenities, and activities, with each day allowing for up to five hours of cruising time.
Welcome aboard! Savor a welcoming glass of champagne as you acquaint yourself with your dedicated crew members, who will be at your beck and call throughout your charter. These knowledgeable crew members are committed to ensuring your voyage is a once-in-a-lifetime experience, tending to your every need and crafting the journey of your dreams.
Day 3
Newport to Block Island
Let's sail the seas!
Today, your destination is Block Island, a haven for biking, birdwatching, and tales of Captain Kidd's hidden treasures. This nature enthusiast's paradise boasts numerous hiking trails and is encircled by over 27 kilometers of pristine, serene beaches.
Embark on an exploration of one of Rhode Island's most picturesque spots, Block Island, with a private guide. Often referred to as "The Bermuda of the North" for its crystal-clear waters, untamed shorelines, lighthouses, and dramatic cliffs, Block Island offers a unique experience. Your knowledgeable private guide will lead you to the Mohegan Bluffs, providing an excellent photo opportunity and sharing the island's captivating history and natural beauty.
Day 3
Newport to Block Island
Let's sail the seas!
Today, your destination is Block Island, a haven for biking, birdwatching, and tales of Captain Kidd's hidden treasures. This nature enthusiast's paradise boasts numerous hiking trails and is encircled by over 27 kilometers of pristine, serene beaches.
Embark on an exploration of one of Rhode Island's most picturesque spots, Block Island, with a private guide. Often referred to as "The Bermuda of the North" for its crystal-clear waters, untamed shorelines, lighthouses, and dramatic cliffs, Block Island offers a unique experience. Your knowledgeable private guide will lead you to the Mohegan Bluffs, providing an excellent photo opportunity and sharing the island's captivating history and natural beauty.
Day 3
Newport to Block Island
Let's sail the seas!
Today, your destination is Block Island, a haven for biking, birdwatching, and tales of Captain Kidd's hidden treasures. This nature enthusiast's paradise boasts numerous hiking trails and is encircled by over 27 kilometers of pristine, serene beaches.
Embark on an exploration of one of Rhode Island's most picturesque spots, Block Island, with a private guide. Often referred to as "The Bermuda of the North" for its crystal-clear waters, untamed shorelines, lighthouses, and dramatic cliffs, Block Island offers a unique experience. Your knowledgeable private guide will lead you to the Mohegan Bluffs, providing an excellent photo opportunity and sharing the island's captivating history and natural beauty.
Day 4
Block Island to Martha's Vineyard
Martha's Vineyard
The charming Martha's Vineyard, a tiny island, serves as a picturesque retreat, drawing yacht charter enthusiasts during the summer and year-round residents seeking its artistic ambiance and unhurried lifestyle. Scattered with quaint towns and lovely villages, the island offers something for everyone, whether it's basking on its stunning beaches, fishing in its well-stocked waters, or delving into its rich cultural heritage. Additionally, food enthusiasts and shopaholics alike will find ample indulgences on this beautiful island.
Join your private guide to uncover the treasures of Martha's Vineyard, often referred to as the "Storybook Island." The island is brimming with delightful surprises, and your guide will lead you to Oak Bluffs' Gingerbread Cottage area, drive you along the beach where the famous movie "Jaws" was filmed, and provide insight into the history of Edgartown, where you'll have some leisure time for shopping.
To wrap up your day, relish the convenience of pre-arranged dinner reservations at the restaurant of your choosing, along with the luxury of a private driver at your service for the evening.
Day 4
Block Island to Martha's Vineyard
Martha's Vineyard
The charming Martha's Vineyard, a tiny island, serves as a picturesque retreat, drawing yacht charter enthusiasts during the summer and year-round residents seeking its artistic ambiance and unhurried lifestyle. Scattered with quaint towns and lovely villages, the island offers something for everyone, whether it's basking on its stunning beaches, fishing in its well-stocked waters, or delving into its rich cultural heritage. Additionally, food enthusiasts and shopaholics alike will find ample indulgences on this beautiful island.
Join your private guide to uncover the treasures of Martha's Vineyard, often referred to as the "Storybook Island." The island is brimming with delightful surprises, and your guide will lead you to Oak Bluffs' Gingerbread Cottage area, drive you along the beach where the famous movie "Jaws" was filmed, and provide insight into the history of Edgartown, where you'll have some leisure time for shopping.
To wrap up your day, relish the convenience of pre-arranged dinner reservations at the restaurant of your choosing, along with the luxury of a private driver at your service for the evening.
Day 4
Block Island to Martha's Vineyard
Martha's Vineyard
The charming Martha's Vineyard, a tiny island, serves as a picturesque retreat, drawing yacht charter enthusiasts during the summer and year-round residents seeking its artistic ambiance and unhurried lifestyle. Scattered with quaint towns and lovely villages, the island offers something for everyone, whether it's basking on its stunning beaches, fishing in its well-stocked waters, or delving into its rich cultural heritage. Additionally, food enthusiasts and shopaholics alike will find ample indulgences on this beautiful island.
Join your private guide to uncover the treasures of Martha's Vineyard, often referred to as the "Storybook Island." The island is brimming with delightful surprises, and your guide will lead you to Oak Bluffs' Gingerbread Cottage area, drive you along the beach where the famous movie "Jaws" was filmed, and provide insight into the history of Edgartown, where you'll have some leisure time for shopping.
To wrap up your day, relish the convenience of pre-arranged dinner reservations at the restaurant of your choosing, along with the luxury of a private driver at your service for the evening.
Day 5
Martha's Vineyard to Nantucket
The Adventure Goes On...
Nantucket, aptly named "The Faraway Land," boasts dune-backed beaches and charming cedar-shingled buildings, evoking a nostalgic sense of stepping back in time. The close-knit island community fosters an intimate atmosphere, and its warm and welcoming ambiance beckons travelers to return year after year. With an abundance of exquisite dining options and a thriving culture of art galleries, unique boutiques, and shopping districts, you'll find yourself spoiled for choice on this stylish island.
Take advantage of a leisurely afternoon to delve deeper into Nantucket's treasures or simply relax back on your yacht.
Day 5
Martha's Vineyard to Nantucket
The Adventure Goes On...
Nantucket, aptly named "The Faraway Land," boasts dune-backed beaches and charming cedar-shingled buildings, evoking a nostalgic sense of stepping back in time. The close-knit island community fosters an intimate atmosphere, and its warm and welcoming ambiance beckons travelers to return year after year. With an abundance of exquisite dining options and a thriving culture of art galleries, unique boutiques, and shopping districts, you'll find yourself spoiled for choice on this stylish island.
Take advantage of a leisurely afternoon to delve deeper into Nantucket's treasures or simply relax back on your yacht.
Day 5
Martha's Vineyard to Nantucket
The Adventure Goes On...
Nantucket, aptly named "The Faraway Land," boasts dune-backed beaches and charming cedar-shingled buildings, evoking a nostalgic sense of stepping back in time. The close-knit island community fosters an intimate atmosphere, and its warm and welcoming ambiance beckons travelers to return year after year. With an abundance of exquisite dining options and a thriving culture of art galleries, unique boutiques, and shopping districts, you'll find yourself spoiled for choice on this stylish island.
Take advantage of a leisurely afternoon to delve deeper into Nantucket's treasures or simply relax back on your yacht.
Day 6
Nantucket
Experience the signature sights in ultimate style.
The Nantucket adventure continues today.
Embark on a journey to uncover the picturesque charm of Nantucket, delving deep into the heart of this captivating destination. Immerse yourself in the relaxed ambiance of this postcard-worthy island, situated 30 miles off the Cape Cod coast. Nantucket beckons with opportunities for swimming, surfing, boutique shopping, fishing, and indulging in delectable fresh seafood. Meet your exclusive guide who will unveil the hidden treasures of Nantucket Island. Your guide will lead you on an exploration of the island, revealing its natural beauty and storied past. You'll have the pleasure of a private tour and tasting at Cisco Brewery before returning to your yacht.
Day 6
Nantucket
Experience the signature sights in ultimate style.
The Nantucket adventure continues today.
Embark on a journey to uncover the picturesque charm of Nantucket, delving deep into the heart of this captivating destination. Immerse yourself in the relaxed ambiance of this postcard-worthy island, situated 30 miles off the Cape Cod coast. Nantucket beckons with opportunities for swimming, surfing, boutique shopping, fishing, and indulging in delectable fresh seafood. Meet your exclusive guide who will unveil the hidden treasures of Nantucket Island. Your guide will lead you on an exploration of the island, revealing its natural beauty and storied past. You'll have the pleasure of a private tour and tasting at Cisco Brewery before returning to your yacht.
Day 6
Nantucket
Experience the signature sights in ultimate style.
The Nantucket adventure continues today.
Embark on a journey to uncover the picturesque charm of Nantucket, delving deep into the heart of this captivating destination. Immerse yourself in the relaxed ambiance of this postcard-worthy island, situated 30 miles off the Cape Cod coast. Nantucket beckons with opportunities for swimming, surfing, boutique shopping, fishing, and indulging in delectable fresh seafood. Meet your exclusive guide who will unveil the hidden treasures of Nantucket Island. Your guide will lead you on an exploration of the island, revealing its natural beauty and storied past. You'll have the pleasure of a private tour and tasting at Cisco Brewery before returning to your yacht.
Day 7
Nantucket to Martha's Vineyard
Sunshine and sandy shores.
Depart from Nantucket and set sail for a return journey to the enchanting Martha's Vineyard. Here, a treasure trove of delights awaits your exploration – pristine sandy beaches, elegant sailboats, vibrant gingerbread cottages, and lighthouses bathed in the hues of a stunning sunset. Embrace the VIP experience and keep your eyes peeled for potential celebrity sightings. Martha's Vineyard boasts an abundance of world-class beaches, seasonal cultural events, and a warm, welcoming atmosphere. Experience firsthand why this remarkable haven draws visitors from across the globe.
No yacht adventure is complete without an array of entertaining toys that cater to guests of all ages and experience levels. From inflatable floats and slides to jet skis, seabobs, or paddleboards, let the aquatic fun commence as you enjoy quality time in the water. If you have a special request not listed among the toys, allow us to arrange a rental, ensuring everyone can enjoy their favorite water-based activities or that electric-powered board they've been eager to try. The crew will orchestrate unforgettable aquatic experiences for all guests to relish.
Day 7
Nantucket to Martha's Vineyard
Sunshine and sandy shores.
Depart from Nantucket and set sail for a return journey to the enchanting Martha's Vineyard. Here, a treasure trove of delights awaits your exploration – pristine sandy beaches, elegant sailboats, vibrant gingerbread cottages, and lighthouses bathed in the hues of a stunning sunset. Embrace the VIP experience and keep your eyes peeled for potential celebrity sightings. Martha's Vineyard boasts an abundance of world-class beaches, seasonal cultural events, and a warm, welcoming atmosphere. Experience firsthand why this remarkable haven draws visitors from across the globe.
No yacht adventure is complete without an array of entertaining toys that cater to guests of all ages and experience levels. From inflatable floats and slides to jet skis, seabobs, or paddleboards, let the aquatic fun commence as you enjoy quality time in the water. If you have a special request not listed among the toys, allow us to arrange a rental, ensuring everyone can enjoy their favorite water-based activities or that electric-powered board they've been eager to try. The crew will orchestrate unforgettable aquatic experiences for all guests to relish.
Day 7
Nantucket to Martha's Vineyard
Sunshine and sandy shores.
Depart from Nantucket and set sail for a return journey to the enchanting Martha's Vineyard. Here, a treasure trove of delights awaits your exploration – pristine sandy beaches, elegant sailboats, vibrant gingerbread cottages, and lighthouses bathed in the hues of a stunning sunset. Embrace the VIP experience and keep your eyes peeled for potential celebrity sightings. Martha's Vineyard boasts an abundance of world-class beaches, seasonal cultural events, and a warm, welcoming atmosphere. Experience firsthand why this remarkable haven draws visitors from across the globe.
No yacht adventure is complete without an array of entertaining toys that cater to guests of all ages and experience levels. From inflatable floats and slides to jet skis, seabobs, or paddleboards, let the aquatic fun commence as you enjoy quality time in the water. If you have a special request not listed among the toys, allow us to arrange a rental, ensuring everyone can enjoy their favorite water-based activities or that electric-powered board they've been eager to try. The crew will orchestrate unforgettable aquatic experiences for all guests to relish.
Day 8
Martha's Vineyard to Hadley Harbor
Take Off
The adventure continues as you make your way to the Elizabeth Islands, a cluster of small islands that span the southern coastline of Cape Cod. Revel in the epitome of island living as you cruise gracefully aboard your luxurious yacht. Spend your day indulging in swimming before embarking on a voyage to Hadley's Harbor. Nestled amidst pastures and pine trees at the eastern tip of Naushon Island, Hadley's Harbor is a hidden oasis that transports you to bygone days. Here, cars are a rarity, and transportation is limited to walking, sailing, and horseback riding.
Whether your yacht charter revolves around commemorating a guest's birthday, marking a special anniversary milestone, or simply enjoying a delightful evening with friends and family, the Chef and Chief Stewardess have a wealth of creative ideas to keep you engaged and entertained. From a thrilling pirate treasure hunt to a lively casino night with live games, as well as Mexican or tropical-themed menus and attire, no detail will be overlooked in crafting an evening that is both exceptional and unforgettable. Your meticulously designed menu, complete with cocktail pairings, decorations, and costumes, will ensure the perfect night aboard your yacht, leaving you with cherished photographs and memories that will endure for years to come.
Day 8
Martha's Vineyard to Hadley Harbor
Take Off
The adventure continues as you make your way to the Elizabeth Islands, a cluster of small islands that span the southern coastline of Cape Cod. Revel in the epitome of island living as you cruise gracefully aboard your luxurious yacht. Spend your day indulging in swimming before embarking on a voyage to Hadley's Harbor. Nestled amidst pastures and pine trees at the eastern tip of Naushon Island, Hadley's Harbor is a hidden oasis that transports you to bygone days. Here, cars are a rarity, and transportation is limited to walking, sailing, and horseback riding.
Whether your yacht charter revolves around commemorating a guest's birthday, marking a special anniversary milestone, or simply enjoying a delightful evening with friends and family, the Chef and Chief Stewardess have a wealth of creative ideas to keep you engaged and entertained. From a thrilling pirate treasure hunt to a lively casino night with live games, as well as Mexican or tropical-themed menus and attire, no detail will be overlooked in crafting an evening that is both exceptional and unforgettable. Your meticulously designed menu, complete with cocktail pairings, decorations, and costumes, will ensure the perfect night aboard your yacht, leaving you with cherished photographs and memories that will endure for years to come.
Day 8
Martha's Vineyard to Hadley Harbor
Take Off
The adventure continues as you make your way to the Elizabeth Islands, a cluster of small islands that span the southern coastline of Cape Cod. Revel in the epitome of island living as you cruise gracefully aboard your luxurious yacht. Spend your day indulging in swimming before embarking on a voyage to Hadley's Harbor. Nestled amidst pastures and pine trees at the eastern tip of Naushon Island, Hadley's Harbor is a hidden oasis that transports you to bygone days. Here, cars are a rarity, and transportation is limited to walking, sailing, and horseback riding.
Whether your yacht charter revolves around commemorating a guest's birthday, marking a special anniversary milestone, or simply enjoying a delightful evening with friends and family, the Chef and Chief Stewardess have a wealth of creative ideas to keep you engaged and entertained. From a thrilling pirate treasure hunt to a lively casino night with live games, as well as Mexican or tropical-themed menus and attire, no detail will be overlooked in crafting an evening that is both exceptional and unforgettable. Your meticulously designed menu, complete with cocktail pairings, decorations, and costumes, will ensure the perfect night aboard your yacht, leaving you with cherished photographs and memories that will endure for years to come.
Day 9
Hadley Harbor to Newport
Safe travels!
Set sail on a course back to where it all began, returning to Newport. As your adventure comes to a close, bid farewell to your dedicated crew and prepare to make your way to the airport for your journey back home. Until we meet again! Your private driver will be waiting to provide you with a seamless airport transfer.
Day 9
Hadley Harbor to Newport
Safe travels!
Set sail on a course back to where it all began, returning to Newport. As your adventure comes to a close, bid farewell to your dedicated crew and prepare to make your way to the airport for your journey back home. Until we meet again! Your private driver will be waiting to provide you with a seamless airport transfer.
Day 9
Hadley Harbor to Newport
Safe travels!
Set sail on a course back to where it all began, returning to Newport. As your adventure comes to a close, bid farewell to your dedicated crew and prepare to make your way to the airport for your journey back home. Until we meet again! Your private driver will be waiting to provide you with a seamless airport transfer.
04
evyssa recommends
Handpicked accommodations for your
relaxation
Handpicked accommodations for your relaxation
Four Seasons Hotel Boston
Nestled alongside the Victorian brownstone homes of the Back Bay neighborhood, the Four Seasons Hotel Boston offers a haven of luxury. This opulent hotel serves as the perfect hub for immersing yourself in the charms of "America's Walking City," as its prime location places top attractions within mere steps. Embark on the historic Freedom Trail, peruse the renowned boutiques that grace Newbury Street, or luxuriate in the comfort of your newly renovated room, affording picturesque views of the storied Public Garden or Beacon Hill. With a total of 273 expansive guest rooms and suites, your accommodation exudes spaciousness, while select options feature bay windows that can be opened to welcome in invigorating breezes.
Following a day of exploration, unwind at the Bristo Bar, where signature Martinis find their perfect complement in delectable bar bites. Alternatively, treat yourself to the epitome of culinary delights at The Bristol, indulging in signature dishes that exemplify gourmet excellence. Enhancing your stay, the hotel offers an array of additional luxuries, including a state-of-the-art fitness center, a heated indoor pool for invigorating swims, and a spa replete with massage services that invite you to embrace complete relaxation and rejuvenation. From location to opulence, every facet of the Four Seasons Hotel Boston promises an unforgettable experience.
Four Seasons Hotel Boston
Nestled alongside the Victorian brownstone homes of the Back Bay neighborhood, the Four Seasons Hotel Boston offers a haven of luxury. This opulent hotel serves as the perfect hub for immersing yourself in the charms of "America's Walking City," as its prime location places top attractions within mere steps. Embark on the historic Freedom Trail, peruse the renowned boutiques that grace Newbury Street, or luxuriate in the comfort of your newly renovated room, affording picturesque views of the storied Public Garden or Beacon Hill. With a total of 273 expansive guest rooms and suites, your accommodation exudes spaciousness, while select options feature bay windows that can be opened to welcome in invigorating breezes.
Following a day of exploration, unwind at the Bristo Bar, where signature Martinis find their perfect complement in delectable bar bites. Alternatively, treat yourself to the epitome of culinary delights at The Bristol, indulging in signature dishes that exemplify gourmet excellence. Enhancing your stay, the hotel offers an array of additional luxuries, including a state-of-the-art fitness center, a heated indoor pool for invigorating swims, and a spa replete with massage services that invite you to embrace complete relaxation and rejuvenation. From location to opulence, every facet of the Four Seasons Hotel Boston promises an unforgettable experience.
Four Seasons Hotel Boston
Nestled alongside the Victorian brownstone homes of the Back Bay neighborhood, the Four Seasons Hotel Boston offers a haven of luxury. This opulent hotel serves as the perfect hub for immersing yourself in the charms of "America's Walking City," as its prime location places top attractions within mere steps. Embark on the historic Freedom Trail, peruse the renowned boutiques that grace Newbury Street, or luxuriate in the comfort of your newly renovated room, affording picturesque views of the storied Public Garden or Beacon Hill. With a total of 273 expansive guest rooms and suites, your accommodation exudes spaciousness, while select options feature bay windows that can be opened to welcome in invigorating breezes.
Following a day of exploration, unwind at the Bristo Bar, where signature Martinis find their perfect complement in delectable bar bites. Alternatively, treat yourself to the epitome of culinary delights at The Bristol, indulging in signature dishes that exemplify gourmet excellence. Enhancing your stay, the hotel offers an array of additional luxuries, including a state-of-the-art fitness center, a heated indoor pool for invigorating swims, and a spa replete with massage services that invite you to embrace complete relaxation and rejuvenation. From location to opulence, every facet of the Four Seasons Hotel Boston promises an unforgettable experience.
Milestone Motor Yacht
At 146 feet (44.5 meters) in length, the Milestone stands as a testament to Christensen's utmost customization. From its sophisticated interior to its expansive outdoor living spaces, charter guests will revel in the abundance of lavish amenities provided by this superyacht. The interior of the luxury yacht serves as a striking exhibition of exquisite craftsmanship, featuring splendid maple and sycamore joinery harmonized with elegant furnishings and premium marble accents. Throughout the yacht, charter guests can bask in the lavish comfort that permeates every corner, fostering relaxation while unwinding in the main salon. Moreover, Milestone's sky lounge offers cinema-style seating for post-water activities movie enjoyment. This versatile space seamlessly transforms into a dance floor, inviting charter guests to dance the night away and create enduring memories.
Milestone Motor Yacht
At 146 feet (44.5 meters) in length, the Milestone stands as a testament to Christensen's utmost customization. From its sophisticated interior to its expansive outdoor living spaces, charter guests will revel in the abundance of lavish amenities provided by this superyacht. The interior of the luxury yacht serves as a striking exhibition of exquisite craftsmanship, featuring splendid maple and sycamore joinery harmonized with elegant furnishings and premium marble accents. Throughout the yacht, charter guests can bask in the lavish comfort that permeates every corner, fostering relaxation while unwinding in the main salon. Moreover, Milestone's sky lounge offers cinema-style seating for post-water activities movie enjoyment. This versatile space seamlessly transforms into a dance floor, inviting charter guests to dance the night away and create enduring memories.
Milestone Motor Yacht
At 146 feet (44.5 meters) in length, the Milestone stands as a testament to Christensen's utmost customization. From its sophisticated interior to its expansive outdoor living spaces, charter guests will revel in the abundance of lavish amenities provided by this superyacht. The interior of the luxury yacht serves as a striking exhibition of exquisite craftsmanship, featuring splendid maple and sycamore joinery harmonized with elegant furnishings and premium marble accents. Throughout the yacht, charter guests can bask in the lavish comfort that permeates every corner, fostering relaxation while unwinding in the main salon. Moreover, Milestone's sky lounge offers cinema-style seating for post-water activities movie enjoyment. This versatile space seamlessly transforms into a dance floor, inviting charter guests to dance the night away and create enduring memories.
As a Virtuoso travel agency, we don’t just book your stay, we help elevate it. At select Virtuoso-preferred properties, we can add special privileges such as complimentary breakfast, resort credits, room upgrades, early check-in, and late check-out, subject to availability.
As a Virtuoso travel agency, we don’t just book your stay, we help elevate it. At select Virtuoso-preferred properties, we can add special privileges such as complimentary breakfast, resort credits, room upgrades, early check-in, and late check-out, subject to availability.
As a Virtuoso travel agency, we don’t just book your stay, we help elevate it. At select Virtuoso-preferred properties, we can add special privileges such as complimentary breakfast, resort credits, room upgrades, early check-in, and late check-out, subject to availability.
05
Pricing
Typical Trip Investment
Contact us for pricing.
Contact us for pricing.
What is a Typical Trip Investment?
To help you plan, many of our sample itineraries include a Typical Trip Investment rather than a fixed price.
Because every Evyssa journey is custom designed, pricing varies based on your travel dates, availability, room category, airfare (when included), exchange rates, and the experiences you choose. Instead of providing a price that may no longer be available when you’re ready to book, we offer a realistic investment range based on what similar trips typically cost.
Our Typical Trip Investment reflects the itinerary shown and is generally based on:
Double occupancy
Luxury accommodations similar to those featured
The private transfers, tours, and experiences described
Typical seasonal pricing at the time the itinerary was created
Standard service levels unless otherwise noted
Final pricing is confirmed only after your travel dates and preferences are finalized and suppliers confirm availability. During the planning process, we’ll present the best available options and pricing for your specific trip, along with any alternatives that may offer greater value.
Our goal is complete transparency—so you’ll always understand what is included, what may affect pricing, and how to make informed decisions before booking.
What is a Typical Trip Investment?
To help you plan, many of our sample itineraries include a Typical Trip Investment rather than a fixed price.
Because every Evyssa journey is custom designed, pricing varies based on your travel dates, availability, room category, airfare (when included), exchange rates, and the experiences you choose. Instead of providing a price that may no longer be available when you’re ready to book, we offer a realistic investment range based on what similar trips typically cost.
Our Typical Trip Investment reflects the itinerary shown and is generally based on:
Double occupancy
Luxury accommodations similar to those featured
The private transfers, tours, and experiences described
Typical seasonal pricing at the time the itinerary was created
Standard service levels unless otherwise noted
Final pricing is confirmed only after your travel dates and preferences are finalized and suppliers confirm availability. During the planning process, we’ll present the best available options and pricing for your specific trip, along with any alternatives that may offer greater value.
Our goal is complete transparency—so you’ll always understand what is included, what may affect pricing, and how to make informed decisions before booking.
LUXURY TRAVEL ARRANGEMENT SERVICES
How do we work?
Our work is based on years of experience, in-person and online training, extensive travel, vast industry affiliations, and a big network of reliable partners — all to enhance your vacation and ensure a seamless planning and booking experience, as well as memories of trips to last a lifetime.
LUXURY TRAVEL ARRANGEMENT SERVICES
How do we work?
Our work is based on years of experience, in-person and online training, extensive travel, vast industry affiliations, and a big network of reliable partners — all to enhance your vacation and ensure a seamless planning and booking experience, as well as memories of trips to last a lifetime.
LUXURY TRAVEL ARRANGEMENT SERVICES
How do we work?
Our work is based on years of experience, in-person and online training, extensive travel, vast industry affiliations, and a big network of reliable partners — all to enhance your vacation and ensure a seamless planning and booking experience, as well as memories of trips to last a lifetime.
Words of Delight about evyssa
Hear from Our Satisfied Travelers!
We love to make our clients happy! And we love to hear their feedback after they returned from vacation. Here are a few of them.
Words of Delight about evyssa
Hear from Our Satisfied Travelers!
We love to make our clients happy! And we love to hear their feedback after they returned from vacation. Here are a few of them.
Words of Delight about evyssa
Hear from Our Satisfied Travelers!
We love to make our clients happy! And we love to hear their feedback after they returned from vacation. Here are a few of them.
plan your travel today
Anticipation is killing you?
Let’s get ahead of the game.
We know the feeling, that spark when you start imagining the next adventure. So why wait? Set the direction, and we’ll refine it from there. Explore how your journey could unfold, then let us make it unmistakably yours.
plan your travel today
Anticipation is killing you?
Let’s get ahead of the game.
We know the feeling, that spark when you start imagining the next adventure. So why wait? Set the direction, and we’ll refine it from there. Explore how your journey could unfold, then let us make it unmistakably yours.
plan your travel today
Anticipation is killing you?
Let’s get ahead of the game.
We know the feeling, that spark when you start imagining the next adventure. So why wait? Set the direction, and we’ll refine it from there. Explore how your journey could unfold, then let us make it unmistakably yours.
important details
Inclusions & Exclusions
Inclusions
At Evyssa Vacations, we believe your trip should be a reflection of your unique desires and experiences. That’s why we offer a range of accommodations, from lavish 5-star hotels to charming boutique inns, all handpicked to suit your personal style.
We’ll work closely with you to craft an itinerary that explores the must-see attractions and hidden local gems, ensuring you embark on a journey that truly resonates with you. Whether you’re celebrating a milestone or seeking personal discovery, our team will pour their hearts into creating the vacation of your dreams, with no fixed schedules to hold you back.
While your international flights and travel insurance are not included, we’re here to assist you every step of the way. Our team can offer recommendations and support to protect your investment and give you peace of mind.
At the end of the day, we’re not just selling you a package - we’re crafting a deeply personal adventure that will leave an indelible mark on your heart. Let us be your guide as you embark on the trip of a lifetime.
Exclusions
Airfare
*We have consolidator and published airfare contracts available with all major airlines. If you’d like our assistance in securing your flight itinerary, please submit your request by clicking HERE.
Travel Insurance
*Our preferred travel insurance partner is Travel Insured. We recommend the Worldwide Trip Protector policy. Submit your Travel Insurance Request by clicking HERE or access their website by clicking HERE to get a quote and purchase the policy. Coverage and policy details HERE.
Terms and Conditions
See Global Voyages Inc. dba Evyssa Vacations' Terms and Conditions by clicking HERE.
FAQ
Questions? We have answers.
Why is Our Professional Retainer Non-Refundable?
How Many Quotes Does Your Retainer Include?
Does My Paid Retainer Expire?
Are These Retainers Your Service Fee for Booking My Trip?
How Do You Get Paid for Your Work?
Do I Pay More Because of Your Retainers and Service Fees?
Is Itemized Pricing Available?
Do You Offer a Best-Price Guarantee?
How Do You Choose Which Suppliers to Use for My Vacation?
FAQ
Questions?
We have answers.
Why is Our Professional Retainer Non-Refundable?
How Many Quotes Does Your Retainer Include?
Does My Paid Retainer Expire?
Are These Retainers Your Service Fee for Booking My Trip?
How Do You Get Paid for Your Work?
Do I Pay More Because of Your Retainers and Service Fees?
Is Itemized Pricing Available?
Do You Offer a Best-Price Guarantee?
How Do You Choose Which Suppliers to Use for My Vacation?
FAQ
Questions? We have answers.
Why is Our Professional Retainer Non-Refundable?
How Many Quotes Does Your Retainer Include?
Does My Paid Retainer Expire?
Are These Retainers Your Service Fee for Booking My Trip?
How Do You Get Paid for Your Work?
Do I Pay More Because of Your Retainers and Service Fees?
Is Itemized Pricing Available?
Do You Offer a Best-Price Guarantee?
How Do You Choose Which Suppliers to Use for My Vacation?
Hire your luxury travel agent
Ready, set, sail!
Secure your spot today and set sail on a cruise filled with luxury, excitement, and endless memories. Embark on the voyage of a lifetime!
Ideas based on our experience.
Making the best decisions.
Custom itineraries.
Hire your luxury
travel agent
Ready, set, sail!
Secure your spot today and set sail on a cruise filled with luxury, excitement, and endless memories. Embark on the voyage of a lifetime!
Ideas based on our experience.
Making the best decisions.
Custom itineraries.
IN THE SPOTLIGHT
As Seen In
We’re grateful that our passion for extraordinary travel experiences is recognized and shared by trusted voices and storytellers.
IN THE SPOTLIGHT
As Seen In
We’re grateful that our passion for extraordinary travel experiences is recognized and shared by trusted voices and storytellers.
IN THE SPOTLIGHT
As Seen In
We’re grateful that our passion for extraordinary travel experiences is recognized and shared by trusted voices and storytellers.
What you will receive
First-hand knowledge
Our team brings you a wealth of expertise built from personal visits to destinations, industry certifications, participation in leading travel conferences, and strong local connections through our land operators. This extensive knowledge allows us to provide practical insights and insider recommendations for your journey.
Handpicked Premium Partners
We aim to connect you with trusted partners—including accommodations, guides, and local providers—selected through rigorous standards and direct experience. Our recommendations are intended to offer quality and unique opportunities, while allowing flexibility based on your preferences and budget.
Around the Clock Support
Travel with peace of mind knowing you have assistance before, during and after your trip. Whether you encounter an issue or need assistance, dedicated support is available to help you resolve problems.
End-to-End Travel Planning Services
We can handle every detail of your journey, from the first idea to your return home. Our advisors design seamless itineraries, anticipate challenges, and ensure nothing is overlooked, making your trip as smooth and enjoyable as possible—while giving you the flexibility to choose the extent of services that fit your preferences.
Hassle-Free Planning
Preparing for your trip can be straightforward with our guidance. We assist you every step of the way with information about entry requirements, sharing practical travel tips, in-depth destination information, proper travel insurance options, and more. We aim to help you stay organized and confident, so you can focus on looking forward to your journey rather than worrying about the details.
Personal Travel App
Itinerary details, tickets, and travel confirmations—all in one place. Our platform keeps your essential travel documents organized and easy to access whenever you need them. With everything consolidated in a single location, you can quickly review your plans, make updates if needed, and travel with greater peace of mind knowing that all your important information is at your fingertips.
What you will receive
First-hand knowledge
Our team brings you a wealth of expertise built from personal visits to destinations, industry certifications, participation in leading travel conferences, and strong local connections through our land operators. This extensive knowledge allows us to provide practical insights and insider recommendations for your journey.
Handpicked Premium Partners
We aim to connect you with trusted partners—including accommodations, guides, and local providers—selected through rigorous standards and direct experience. Our recommendations are intended to offer quality and unique opportunities, while allowing flexibility based on your preferences and budget.
Around the Clock Support
Travel with peace of mind knowing you have assistance before, during and after your trip. Whether you encounter an issue or need assistance, dedicated support is available to help you resolve problems.
End-to-End Travel Planning Services
We can handle every detail of your journey, from the first idea to your return home. Our advisors design seamless itineraries, anticipate challenges, and ensure nothing is overlooked, making your trip as smooth and enjoyable as possible—while giving you the flexibility to choose the extent of services that fit your preferences.
Hassle-Free Planning
Preparing for your trip can be straightforward with our guidance. We assist you every step of the way with information about entry requirements, sharing practical travel tips, in-depth destination information, proper travel insurance options, and more. We aim to help you stay organized and confident, so you can focus on looking forward to your journey rather than worrying about the details.
Personal Travel App
Itinerary details, tickets, and travel confirmations—all in one place. Our platform keeps your essential travel documents organized and easy to access whenever you need them. With everything consolidated in a single location, you can quickly review your plans, make updates if needed, and travel with greater peace of mind knowing that all your important information is at your fingertips.
What you will receive
First-hand knowledge
Our team brings you a wealth of expertise built from personal visits to destinations, industry certifications, participation in leading travel conferences, and strong local connections through our land operators. This extensive knowledge allows us to provide practical insights and insider recommendations for your journey.
Handpicked Premium Partners
We aim to connect you with trusted partners—including accommodations, guides, and local providers—selected through rigorous standards and direct experience. Our recommendations are intended to offer quality and unique opportunities, while allowing flexibility based on your preferences and budget.
Around the Clock Support
Travel with peace of mind knowing you have assistance before, during and after your trip. Whether you encounter an issue or need assistance, dedicated support is available to help you resolve problems.
End-to-End Travel Planning Services
We can handle every detail of your journey, from the first idea to your return home. Our advisors design seamless itineraries, anticipate challenges, and ensure nothing is overlooked, making your trip as smooth and enjoyable as possible—while giving you the flexibility to choose the extent of services that fit your preferences.
Hassle-Free Planning
Preparing for your trip can be straightforward with our guidance. We assist you every step of the way with information about entry requirements, sharing practical travel tips, in-depth destination information, proper travel insurance options, and more. We aim to help you stay organized and confident, so you can focus on looking forward to your journey rather than worrying about the details.
Personal Travel App
Itinerary details, tickets, and travel confirmations—all in one place. Our platform keeps your essential travel documents organized and easy to access whenever you need them. With everything consolidated in a single location, you can quickly review your plans, make updates if needed, and travel with greater peace of mind knowing that all your important information is at your fingertips.
We are a team of expert travel agents specialized in luxury international travel planning. With decades of experience in both traveling and planning trips for others, we are here to help you make that dream vacation come true. Getting to know YOU, our customer, and giving our professional all to earn your trust is what we are about. We aim to excel in customer service, so that you can sit back, relax and enjoy your vacation.
Our team at Evyssa Vacations (formerly known as Global Voyages Inc.) has been creating memories and serving our clients since 2009, and we look forward to working with you on your next luxury getaway!
We're located in Hoffman Estates, Chicago and we are doing our best to be the most helpful travel agency to work with.
Travel Types
Unique group trips
Special vacations
We are a team of expert travel agents specialized in luxury international travel planning. With decades of experience in both traveling and planning trips for others, we are here to help you make that dream vacation come true. Getting to know YOU, our customer, and giving our professional all to earn your trust is what we are about. We aim to excel in customer service, so that you can sit back, relax and enjoy your vacation.
Our team at Evyssa Vacations (formerly known as Global Voyages Inc.) has been creating memories and serving our clients since 2009, and we look forward to working with you on your next luxury getaway!
We're located in Hoffman Estates, Chicago and we are doing our best to be the most helpful travel agency to work with.
Travel types
Unique group trips
Special vacations
destinations
useful links
Copyright © Global Voyages Inc. dba Evyssa Vacations
We are a team of expert travel agents specialized in luxury international travel planning. With decades of experience in both traveling and planning trips for others, we are here to help you make that dream vacation come true. Getting to know YOU, our customer, and giving our professional all to earn your trust is what we are about. We aim to excel in customer service, so that you can sit back, relax and enjoy your vacation.
Our team at Evyssa Vacations (formerly known as Global Voyages Inc.) has been creating memories and serving our clients since 2009, and we look forward to working with you on your next luxury getaway!
We're located in Hoffman Estates, Chicago and we are doing our best to be the most helpful travel agency to work with.
Travel types
Unique group trips
Special vacations
destinations
useful links