Luxury sailing vacations in Massachusetts

Witch of Endor Sailing Charters is a premier travel agency located at 99 Water Street in Tisbury, Massachusetts. We offer unforgettable sailing experiences along the beautiful coastline of Martha's Vineyard. Our expert crew and luxurious vessels ensure a safe and enjoyable journey as you explore the scenic waters of New England. Whether you're looking for a romantic sunset cruise or a thrilling adventure on the open sea, Witch of Endor Sailing Charters has the perfect excursion for you. Book your sailing adventure today and let us help you create memories that will last a lifetime.

Sunset Sail Salem is a premier travel agency located in the historic city of Salem, Massachusetts. Our agency is dedicated to providing unforgettable experiences on the water, offering scenic sunset sails along the picturesque coast of Salem. Our expert crew ensures a safe and enjoyable journey as you relax and take in the stunning views of the sunset over the Atlantic Ocean. Whether you're looking for a romantic evening out or a fun adventure with friends and family, Sunset Sail Salem is the perfect choice for your next nautical excursion. Book your sail today and create lasting memories on the water.

Frayed Knot Sailing Charters is a premier travel agency located at 15 Ashland Avenue in the picturesque coastal town of Manchester-by-the-Sea, Massachusetts. Specializing in unforgettable sailing experiences, our charter services offer unique and personalized excursions on the open waters of the Atlantic Ocean. Whether you're looking for a relaxing sunset cruise or an adventurous day trip, Frayed Knot Sailing Charters has something for everyone. Our experienced crew and luxurious vessels ensure a safe and enjoyable journey for all our guests. Come sail away with us and create memories that will last a lifetime.

Halcyon Days Sailing Charters is a premier travel agency located in Gloucester, Massachusetts, United States. Specializing in unforgettable sailing experiences, Halcyon Days offers a variety of charter options for individuals and groups looking to explore the scenic waters of the New England coast. With expert captains and top-of-the-line vessels, guests can relax and enjoy a luxurious and personalized sailing adventure. Whether you're a seasoned sailor or a first-time explorer, Halcyon Days Sailing Charters promises an unforgettable journey on the open sea.

Classic Sail Boston is a premier travel agency located in the heart of Boston, Massachusetts. Specializing in classic sailboat tours and experiences, our knowledgeable staff are dedicated to providing an unforgettable and authentic maritime adventure. Whether you're looking to explore the historic Boston Harbor or cruise along the picturesque New England coastline, Classic Sail Boston offers a variety of tailored sailing experiences to suit every preference. Come aboard and immerse yourself in the beauty and tranquility of the open sea with Classic Sail Boston.

Paramount Vacations - Melanie Richards is a premier travel agency located at 51 Mill Street in Hanover, Massachusetts, United States. Offering worry-free, expert planning, and unforgettable luxury experiences, this agency provides exclusive perks and upgrades for its clients. Specializing in African wildlife conservation experiences, prestigious golf and tennis tours, and Collette tours to South Africa, Paramount Vacations ensures a memorable and enjoyable trip for all travelers. With Seabourn's 2025-26 expedition cruises and Princess Cruises' "Best Price Guarantee," clients can save on Greenland-Alaska sailings and book early for the best savings. Whether exploring the lush rice fields of Bali, embarking on wildlife photography safaris, or discovering the real man behind St. Patrick's Day, Paramount Vacations offers a diverse range of travel experiences for every adventurer. With Viking's expedition cruise ships equipped with 'yellow submarines' and zodiacs, clients can explore the world's oceans in style. Join Paramount Vacations - Melanie Richards for an unforgettable and luxurious travel experience.

Sail Cape Cod Provincetown is a travel agency located at 9 MacMillan Pier in the picturesque town of Provincetown, Massachusetts. Specializing in sailing excursions and tours, this institution offers visitors the opportunity to explore the stunning waters of Cape Cod in a unique and unforgettable way. Whether you're looking for a relaxing sunset cruise or an adventurous sailing trip, Sail Cape Cod Provincetown has something for everyone. Join them for an experience you won't soon forget.

Moment Sailing Adventures is located at 16 MacMillan Pier in Provincetown, Massachusetts, offering deluxe private captained day sailing charters. With a strict US Coast Guard policy limiting groups to six guests, including children, Moment provides a personalized and intimate sailing experience. The 47-foot Moment, designed by Sparkman & Stephens, offers 2, 4, and 6-hour sails to explore the wildlife, beaches, lighthouses, and sunsets of outer Cape Cod. Recognized as one of the 5 Best Sailing Charters by Yankee Magazine and rated 5 stars on TripAdvisor, Moment Sailing Adventures promises a memorable and safe sailing experience. The vessel underwent an extensive refit in 2013-14 and is equipped with modern amenities such as a guest toilette, refrigeration for beverages, and a tender named "Tary" for shore excursions. Guests rave about their experiences aboard Moment, praising the skilled captain, Chris, for creating unforgettable moments on the water. Whether it's a romantic proposal, a birthday celebration, or a leisurely sail around Provincetown harbor, Moment Sailing Adventures ensures a unique and special experience for all guests.

Cape Cod Catamaran Sailing Charters is a travel agency located at 255 Commercial Street in Wellfleet, Massachusetts, United States. Offering morning and afternoon charters as well as sunset cruises from Wellfleet Harbor, this institution provides an authentic Cape Cod experience on their catamaran, Discovery. Escape the crowds and immerse yourself in the serene beauty of Cape Cod with a private daytime charter, where you can explore the bay, watch seals, or simply relax and enjoy the tranquility of the local waters. The experienced captain ensures a smooth and comfortable ride as you navigate Wellfleet Harbor and Cape Cod Bay.

Come Sail Away Now is a premier travel agency located in the heart of Boston, Massachusetts. Specializing in luxury sailboat vacations, our experienced team of travel experts will help you plan the perfect sailing adventure. Whether you're looking to explore the picturesque New England coast or set sail to exotic destinations around the world, Come Sail Away Now has you covered. Let us take the stress out of vacation planning and help you create memories that will last a lifetime. Visit us at 1 8th Street in Boston and start planning your dream sailing vacation today.

Boston Sail Tours offers unforgettable sailing charters in the beautiful Boston Harbor. Our experienced captains will take you on a journey through the historic waters of Boston, showcasing iconic landmarks such as the USS Constitution and the Boston Tea Party Ships. Whether you are looking for a romantic sunset cruise or a fun-filled day out on the water with friends and family, Boston Sail Tours has the perfect charter for you. Come aboard our luxury sailing vessels and experience the thrill of sailing in one of America's most historic and picturesque harbors. Book your charter today at our location on 28 Constitution Road, Boston, Massachusetts, United States.

Sail The Vineyard is a unique travel agency located at 13 Marine Avenue in Wareham, Massachusetts. Led by an adventurous and accomplished female captain, our all-female crew offers sailing excursions in Martha's Vineyard and The Caribbean. Our captain is a US Coast Guard Master Mariner and a Certified instructor by the American Sailing Association, specializing in mentoring female sailors. Embark on a thrilling adventure aboard our classic sloop-rigged sailboat and explore the beauty and history of Martha's Vineyard by sea. Enjoy the picturesque coastline with lighthouses, historic homes, and beautiful beaches. Feel the wind in your hair, embrace your inner mermaid, and learn the art and science of sailing with us.

The Cruise Store is a premier travel agency located at 145 Shaker Road in East Longmeadow, Massachusetts. Specializing in luxury cruise vacations, our experienced travel agents are dedicated to helping clients plan their dream getaway at sea. From exotic destinations to popular cruise lines, we offer a wide range of options to suit every traveler's preferences. Whether you're looking for a romantic escape, family adventure, or group excursion, The Cruise Store has the expertise and resources to make your vacation unforgettable. Book your next cruise with us and set sail for an unforgettable experience on the high seas.

SV Dream Escapes LLC is a premier travel agency located at 6 Queen Circle in Dudley, Massachusetts, United States. We specialize in creating unforgettable travel experiences for our clients, helping them to escape the ordinary and discover the world's most beautiful destinations. Our team of expert travel planners is dedicated to crafting personalized itineraries that cater to every traveler's unique preferences and desires. Whether you're dreaming of a relaxing beach getaway, an adventurous safari, or a cultural exploration, SV Dream Escapes LLC is here to turn your travel dreams into reality. Contact us today to start planning your next dream escape.

Ship’s Ahoy! is a nautical-themed institution located at 1623 Main Street in Agawam, Massachusetts. Our establishment is a one-of-a-kind maritime experience, offering a wide range of nautical decor, gifts, and accessories for all sea lovers. From ship models to anchor-themed home decor, we have everything you need to bring the ocean into your home. Come visit Ship’s Ahoy! and set sail on a journey of nautical discovery.

Martha's Vineyard Surfside Hotel, located at 7 Oak Bluffs Avenue in Oak Bluffs, Massachusetts, is a premier lodging option on the beautiful island of Martha's Vineyard. This family-owned and operated hotel has been welcoming guests since 1987, offering a cozy and comfortable stay for visitors looking to explore all that the island has to offer. Situated in the heart of Oak Bluffs, Martha's Vineyard Surfside Hotel is the perfect home base for exploring the six charming towns, stunning beaches, and delicious farm-to-table restaurants that make up the island. Whether you're interested in biking, hiking, fishing, or sailing, there is something for everyone to enjoy on Martha's Vineyard.

Isabelle's Beach House is a charming lodging institution located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Our family-owned B&B was founded on the principles of hospitality, warmth, and community, making every guest feel like part of our inclusive community. As a gift of Island Joy, we offer 2024 Gift Certificates for a memorable stay at our beach house. Our newly opened boutique in Oak Bluffs, launched in August 2023, serves as a platform for mission-driven businesses and conscious consumers. Summer boutique hours are from May to October, or shop online 24/7 at www.jubileemv.com.

Truro Beach Cottages, located at 640 Shore Road in Truro, Massachusetts, offers a perfect escape for those looking to relax and unwind by the beach. Guests have raved about the cleanliness of the cottages, especially during these Covid times, and many have returned for another stay. The property is pet-friendly, making it a great option for those looking to bring their furry friends along for a vacation. The cottages provide a comfortable and stylish stay, with new flooring, kitchens, bathrooms, and mini-split AC systems. Guests can relax on the deck chairs and enjoy the stunning views of the dunes and the Atlantic Ocean. A short drive to downtown Truro and Provincetown offers a variety of activities, including art galleries, watersports, dining, and shopping.

The Cottages at Nantucket Boat Basin is a charming lodging option located at 24 Old South Wharf in Nantucket, Massachusetts. This unique institution offers cozy cottages with stunning views of the marina, perfect for a relaxing getaway. As a real estate agency, they also offer opportunities to invest in waterfront properties in this picturesque location. Additionally, as a travel agency, they can help plan your dream vacation to Nantucket, ensuring a memorable experience. Whether you're looking for a weekend retreat or a long-term investment, The Cottages at Nantucket Boat Basin has everything you need for a perfect stay in this beautiful coastal town.

The Colony of Wellfleet is a unique lodging institution located at 640 Chequessett Neck Road in Wellfleet, Massachusetts, United States. Originally designed and built in 1948 by architects Nathaniel Saltonstall and Oliver P. Morton, this institution was known as the Mayo Hill Colony Club, serving as a private club and art gallery for artists and patrons. In 1963, Loris and Eleanor Stefani acquired the cottages and transformed them into a hotel, adding their own creative touches and artwork to create The Colony as it is known today. Managed by their son Jeffrey and his wife Mihae since 2019, The Colony offers a truly special summer retreat in the Northeast. The Colony of Wellfleet features 10 Bauhaus-style cottages overlooking Wellfleet harbor and bay, each designed for elegant functionality and furnished with pieces by leading modernists. Guests can enjoy reserved beach space, golf, tennis, pickleball, sailing lessons, and more at the club. The cafe offers coffee, pastries, lunch, and drinks with stunning views. Flexible membership options are available for guests.

Yachtsman Condo Rentals is a premier real estate and travel agency located at 500 Ocean Street in Barnstable, Massachusetts. Our agency specializes in luxurious condo rentals for yachtsmen looking to explore the beautiful coastal region of Cape Cod. With stunning views of the ocean and top-notch amenities, our condos provide the perfect home away from home for your nautical adventures. Contact us today to book your dream vacation rental with Yachtsman Condo Rentals.

The Mariner House is a charming inn located at 30 Centre Street in the picturesque town of Nantucket, Massachusetts. This historic institution offers a cozy and welcoming atmosphere for guests looking to experience the beauty and charm of the island. With its convenient location near the harbor and local attractions, The Mariner House is the perfect place to stay for a relaxing getaway or a romantic retreat. Guests can enjoy comfortable accommodations, delicious breakfast options, and personalized service from the friendly staff. Whether you're exploring the cobblestone streets of Nantucket or relaxing on the nearby beaches, The Mariner House is the ideal home base for your island adventure.

One Mariners Landing is a prestigious institution situated at the address One Mariners Landing in Edgartown, Massachusetts, United States. This elegant and sophisticated establishment offers a range of luxury amenities and services for its guests. With stunning views of the marina and surrounding area, One Mariners Landing provides a tranquil and upscale setting for visitors to relax and unwind. Whether you are looking for a weekend getaway or a longer stay, this institution is the perfect choice for those seeking a high-end experience in a beautiful coastal town.

Cruises.com is a premier travel agency located at 100 Quannapowitt Parkway in Wakefield, Massachusetts. Specializing in cruises, this institution offers a wide range of vacation packages to exotic destinations around the world. With a team of experienced travel experts, Cruises.com is dedicated to helping customers find the perfect cruise experience tailored to their preferences and budget. Whether you're looking for a relaxing Caribbean getaway or an adventurous Alaskan expedition, Cruises.com has you covered. Book your dream cruise today and set sail for an unforgettable vacation experience.

CheapCruises.com is a leading travel agency located in Wakefield, Massachusetts, United States. As the name suggests, they specialize in offering affordable cruise packages to various destinations around the world. With a wide selection of cruise lines and itineraries to choose from, CheapCruises.com makes it easy for travelers to find the perfect vacation at a great price. Whether you're looking for a quick getaway or an extended adventure at sea, CheapCruises.com has something for everyone. Book your dream cruise today and set sail for an unforgettable experience!

LuxuryOnly Cruises is a premier travel agency located at 100 Quannapowitt Parkway in Wakefield, Massachusetts, United States. Specializing in luxury cruise vacations, we offer a wide range of exclusive cruise packages to some of the most exotic and breathtaking destinations around the world. Our experienced and knowledgeable travel advisors are dedicated to providing top-notch service and creating unforgettable experiences for our clients. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, LuxuryOnly Cruises has the perfect cruise package for you. Book your dream vacation with us today and set sail on a luxury cruise experience like no other.

Compass Rose Yacht Charters is a premier yacht charter company located at 346 Merrimac Street in Newburyport, Massachusetts. As both a school and a travel agency, Compass Rose offers a unique opportunity for individuals to learn about sailing while exploring the beautiful waters of the United States. With a fleet of luxurious yachts and experienced instructors, Compass Rose provides an unforgettable experience for those looking to embark on a sailing adventure. Whether you are a beginner or an experienced sailor, Compass Rose Yacht Charters has something to offer for everyone.

Plan Sea Adventure Charters, located at 53 Dock Street in Edgartown, Massachusetts, is the premier boat tour and rental company in Martha’s Vineyard and Cape Cod. Offering a variety of private cruise packages for groups of up to 18 passengers, our boat tours are perfect for family outings, bachelorette parties, team building events, and more. Our experienced Captains, with U.S. Coast Guard Masters Licenses, ensure a safe and enjoyable experience as you cruise along the beautiful shoreline of Woods Hole and Oak Bluffs. With indoor and outdoor heated seating, a bathroom, and a wet bar on board, our classic New England motor vessels provide a luxurious and comfortable ride for all guests.

Nauti Girl Excursions is a premier tourist attraction and travel agency located at 50 Dock Street in picturesque Edgartown, Massachusetts. Specializing in unique and unforgettable maritime adventures, Nauti Girl Excursions offers a variety of excursions for those looking to explore the beauty of the waters surrounding Martha's Vineyard. Whether you're interested in a relaxing sunset cruise, a thrilling fishing expedition, or a private charter for a special occasion, Nauti Girl Excursions has something for everyone. Come experience the magic of the sea with Nauti Girl Excursions and create memories that will last a lifetime.

Island Girl Excursions is a premier travel agency located at 7 Great Plains Road in West Tisbury, Massachusetts. Specializing in curated experiences for adventurous travelers, Island Girl Excursions offers personalized itineraries and guided tours to explore the stunning natural beauty and cultural richness of Martha's Vineyard and beyond. With a team of experienced travel experts and a commitment to providing top-notch customer service, Island Girl Excursions is your go-to destination for unforgettable travel experiences. Book your next adventure with Island Girl Excursions and embark on a journey of a lifetime.