TOP 30 Luxury sailing adventures in Massachusetts

28 results found

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.

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.

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.

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.

Endeavor Sailing Excursions is a premier sailing company located in Nantucket, Massachusetts. We offer a variety of sailing excursions for all levels of experience, from beginners to seasoned sailors. Our experienced captains will guide you through the beautiful waters surrounding Nantucket, providing a safe and enjoyable experience for all. Whether you're looking for a relaxing sunset cruise or an adventurous day on the water, Endeavor Sailing Excursions has something for everyone. Come join us for an unforgettable sailing experience in one of the most picturesque locations in the United States.

Classic Harbor Line Boston is a premier travel agency located at 60 Rowes Wharf in Boston, Massachusetts. Step aboard one of our classic vessels and fall in love with Boston Harbor as you sail on a schooner or cruise on a motor yacht. Our fleet is historically inspired by turn-of-the-century style yachts, designed with classic elements to create an elegant atmosphere for hosting events such as Nautical Weddings, Corporate Outings, Graduations, and Team Building activities. Experience a fun and luxurious sailing excursion in Boston Harbor with Classic Harbor Line. Sail on the elegant schooner Adirondack III or relax on the motor vessel Northern Lights while taking in breathtaking views of the Boston skyline, historical sites, harbor islands, and wildlife such as harbor seals. Whether you're a first-time visitor or a local, our yachts offer a new perspective on the city of Boston. Kick back and relax as our hospitable crew takes care of everything for you.

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.

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.

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.

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.

Catboat Charters is a premier travel agency located at 1 Dock Street in Edgartown, Massachusetts. Specializing in unique and unforgettable sailing experiences, Catboat Charters offers a variety of charter options for exploring the beautiful waters of Martha's Vineyard and beyond. Whether you're looking for a relaxing sunset cruise or an adventurous day of sailing, Catboat Charters has something for everyone. With experienced captains and top-notch service, Catboat Charters is the perfect choice for your next nautical adventure.

Island Classic Charters is a premier travel agency located in the picturesque town of Chilmark, Massachusetts. Specializing in luxury yacht charters, they offer unforgettable experiences exploring the stunning waters surrounding Martha's Vineyard and the surrounding islands. Whether you're looking for a romantic sunset cruise, a family day trip, or a corporate event, Island Classic Charters has the perfect vessel to suit your needs. With experienced captains and top-notch service, they ensure a seamless and memorable sailing experience for all their guests. Book your next adventure with Island Classic Charters and discover the beauty of the New England coast in style.

Steady As She Goes Charters is a premier travel agency located in the picturesque town of Tisbury, Massachusetts. Specializing in luxury yacht charters, our experienced team is dedicated to providing unforgettable experiences on the water. Whether you're looking for a relaxing day cruise or a week-long adventure, we have the perfect charter for you. Set sail with us and discover the beauty of the Massachusetts coast in style and comfort.

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.

Cruise One is a premier travel agency located at 124 Green Street in Weymouth, Massachusetts. Specializing in luxury cruise vacations, they offer a wide range of cruise packages to destinations around the world. With expert travel agents who are knowledgeable about various cruise lines and itineraries, they are dedicated to helping their clients plan the perfect cruise experience. Whether you are looking for a relaxing Caribbean getaway or an adventurous Alaskan expedition, Cruise One can help you find the ideal cruise vacation tailored to your preferences. Book your dream cruise today with Cruise One and set sail on an unforgettable journey.

Cruise Planners is a reputable travel agency located at 400 Boston Post Road in Sudbury, Massachusetts, United States. Specializing in cruise vacations, the agency offers personalized trip planning services to help clients create unforgettable travel experiences. With a team of experienced travel advisors, Cruise Planners is dedicated to providing top-notch customer service and expert advice to ensure smooth sailing from start to finish. Whether you're looking to explore exotic destinations or relax on a luxurious cruise ship, Cruise Planners has the expertise and resources to make your travel dreams a reality. Contact them today to start planning your next adventure!

The National Charter 957 is a historic institution located at 9 Taunton Green in Taunton, Massachusetts, United States. Originally home to the first National Bank of the United States of America, it has been transformed into Taunton's 1st Late-Night Luxury Craft Cocktail Bar. Come enjoy a unique and sophisticated drinking experience in a setting rich with history and charm.

East Coast Yacht Sales is a premier store located at 17 Ashland Avenue in Manchester-by-the-Sea, Massachusetts. Specializing in yacht sales, this institution offers a wide range of high-quality yachts for sale, catering to both experienced sailors and those new to the world of boating. With a knowledgeable and friendly staff, East Coast Yacht Sales provides exceptional customer service and expert advice to help clients find the perfect yacht for their needs. Whether you are looking to buy your first yacht or upgrade to a larger vessel, East Coast Yacht Sales is the go-to destination for all your boating needs. Visit us today and set sail on your next adventure!

True Blue Waters is a reputable general contractor based in Sterling, Massachusetts. We specialize in providing top-quality construction services for residential and commercial projects. Our team of experienced professionals is dedicated to delivering exceptional results, on time and within budget. From remodeling and renovations to new construction and custom builds, we have the expertise to bring your vision to life. Contact us today at 14b Boutelle Road to discuss your project and see why True Blue Waters is the trusted choice for all your construction needs.