TOP 30 Sailing charter adventures in Massachusetts

43 results found

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.

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.

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.

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.

Sail Ena is a renowned travel agency located at 350 Lake Street in Tisbury, Massachusetts, United States. Specializing in sailing adventures, Sail Ena offers a variety of exciting and unforgettable experiences for those looking to explore the open seas. Whether you're a seasoned sailor or a novice looking to try something new, Sail Ena has something for everyone. With expert guides and top-of-the-line equipment, you can trust that your sailing experience with Sail Ena will be safe, enjoyable, and truly memorable. Book your next sailing adventure with Sail Ena and set sail for an unforgettable journey on the waters of Massachusetts.

OceanQuest Discovery Cruises & Private Charters is a premier travel agency located at 100 Water Street in Falmouth, Massachusetts, United States. We specialize in providing unforgettable ocean adventures through our discovery cruises and private charters. Whether you are looking to explore the beautiful waters of Cape Cod or embark on a personalized sailing experience, our experienced team is dedicated to creating a memorable and thrilling journey for you. Join us for a one-of-a-kind maritime experience and discover the wonders of the ocean with OceanQuest Discovery Cruises & Private Charters.

Sail When And If is a travel agency located at 10 Blaney Street in Salem, Massachusetts, United States. The agency offers sailing excursions on the beautiful historic schooner When And If, originally commissioned by General George S. Patton in 1939. The schooner was built by naval architect John Alden and has a storied past, with a mission to sail around the world "When the war is over, and If I live through it." Experience the beauty of the water with sunset sails in Key West, daily sailing trips in Salem, and private charters available all year round. Whether you are a seasoned sailor or a first-timer, Sail When And If has something for everyone. The schooner When And If is a classic yacht with a rich history and offers an unparalleled sailing experience.

Maritime Heritage Charters is a unique institution located in Gloucester, Massachusetts, United States. As a museum and travel agency, we offer visitors the opportunity to immerse themselves in the rich maritime history of the area. Our location at 23 Harbor Loop provides easy access to the waterfront and a chance to explore historic ships, artifacts, and exhibits. Whether you're interested in booking a charter to sail the open seas or simply want to learn more about the maritime heritage of Gloucester, Maritime Heritage Charters is the perfect destination for maritime enthusiasts of all ages.

Defiance Sail Charters is a premier travel agency located at 211 East Main Street in Gloucester, Massachusetts, United States. Specializing in unforgettable sailing experiences, we offer a variety of charter options for those looking to explore the beautiful waters of the New England coast. Our experienced captains and crew are dedicated to providing exceptional service and ensuring a safe and enjoyable journey for all guests. Whether you're looking for a romantic sunset cruise, a family adventure, or a corporate outing, Defiance Sail Charters has the perfect sailing excursion for you. Book your next nautical adventure with us and set sail for memories that will last a lifetime.

Sail Anejo is a premier travel agency located in Gloucester, Massachusetts, United States. Specializing in sailing adventures, they offer a wide range of services including private charters, sailing lessons, and guided tours of the beautiful coastal waters of New England. With a team of experienced captains and crew members, Sail Anejo ensures a safe and unforgettable experience for all their customers. Whether you are looking for a relaxing day on the water or an exciting sailing excursion, Sail Anejo is your go-to destination for all things nautical. Book your next sailing adventure with Sail Anejo and set sail for an unforgettable experience on the open sea.

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.

ACK Sail is a premier travel agency located at 34 Washington Street in the charming town of Nantucket, Massachusetts. Specializing in unique sailing adventures and excursions, ACK Sail offers a variety of services to help you explore the stunning waters surrounding Nantucket Island. Whether you're looking to charter a private boat for a romantic sunset cruise or join a group excursion to discover hidden coves and marine life, ACK Sail has something for every type of traveler. With experienced captains and a passion for providing unforgettable experiences on the water, ACK Sail is the perfect choice for your next maritime adventure.

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.

Captain Curley's Sailing Charters is a premier travel agency located at 255 Commercial Street in Wellfleet, Massachusetts. Specializing in sailing adventures, they offer a variety of charter options for those looking to explore the beautiful waters of Cape Cod. Whether you're a seasoned sailor or a complete novice, Captain Curley's experienced crew will ensure you have a safe and unforgettable experience on the water. From sunset cruises to day trips to nearby islands, there's something for everyone at Captain Curley's Sailing Charters. Come aboard and set sail on your next adventure!

Two Captains Charters, located at 350 R Merrimac Street in Newburyport, Massachusetts, offers the ultimate fishing and cruising experience. Whether you are looking to reel in striped bass, bluefish, cod, haddock, or even bluefin tuna, or simply enjoy a relaxing cruise along the coast, Two Captains Charters has you covered. With experienced USCG Licensed Captains Ed and Jeff at the helm, you can expect a day filled with fun, excitement, and memorable moments. From baiting your hook to cleaning your fish, the Two Captains Charters team will attend to all your needs. Book now for an unforgettable day on the water in 2023!

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.

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.

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.

Sail Martha's Vineyard is a non-profit organization located at 151 Beach Road in Tisbury, Massachusetts. Our mission is to provide sailing education and experiences to individuals of all ages, backgrounds, and abilities. With a focus on promoting environmental stewardship and maritime heritage, we offer a variety of programs including youth sailing camps, adult sailing lessons, and community events. Our experienced instructors and dedicated staff are committed to creating a safe and inclusive environment where participants can develop their sailing skills and passion for the ocean. Whether you're a beginner looking to learn the basics or an experienced sailor seeking to enhance your abilities, Sail Martha's Vineyard has something for everyone. Join us on the water and discover the joy of sailing on the beautiful waters of Martha's Vineyard.

Jetties Sailing Center is a premier sailing institution located at Bathing Beach Road in Nantucket, Massachusetts. Offering a wide range of sailing programs and lessons for all ages and skill levels, the center is the perfect place to learn and improve your sailing skills. With experienced instructors, top-notch equipment, and a beautiful location on the shores of Nantucket, Jetties Sailing Center is the ultimate destination for anyone looking to enjoy the thrill of sailing on the open water. Come join us and experience the joy of sailing in one of the most picturesque locations in the United States.

Sail Salem is a non-profit organization located at 50 Winter Island Road in Salem, Massachusetts. Our mission is to provide affordable and accessible sailing opportunities for people of all ages and abilities. Whether you are a beginner looking to learn the basics or an experienced sailor wanting to hone your skills, Sail Salem has something for everyone. Our experienced instructors offer a variety of classes and programs, including youth sailing camps, adult lessons, and group outings. Come join us on the water and experience the joy of sailing in the historic city of Salem.

Wild Harbor Sailing is a premier sailing institution located at 386 Grove Street in Falmouth, Massachusetts, United States. Offering a variety of sailing programs for all ages and skill levels, Wild Harbor Sailing provides an exceptional learning experience on the beautiful waters of Cape Cod. With experienced instructors, top-notch equipment, and a passion for the sport, students can expect to improve their sailing skills while enjoying the scenic views of Wild Harbor. Whether you are a beginner looking to learn the basics or an experienced sailor seeking to hone your techniques, Wild Harbor Sailing has something for everyone. Join us for an unforgettable sailing adventure!

Welcome to Steal Away Charters, your premier travel agency located in the heart of Newburyport, Massachusetts. Nestled at 346 Merrimac Street, our business is dedicated to crafting unforgettable maritime adventures for locals and visitors alike. At Steal Away Charters, we specialize in offering personalized and exhilarating charter experiences along the picturesque New England coastline. Whether you’re seeking a serene day of sailing, an exciting fishing expedition, or a customized private event on the water, our expert team is committed to making your nautical dreams come true.

Welcome to Broad Reach Adventures, your gateway to unforgettable sailing experiences along the stunning coastline of Southeast Massachusetts. Located in the historic city of New Bedford, Massachusetts, our travel agency specializes in crafting unique sailing adventures that explore some of the finest locations on the East Coast, including the beautiful Martha's Vineyard. At Broad Reach Adventures, we invite you to embark on a journey aboard the Tortola, a 50-foot high-latitude cutter sloop designed by the renowned Thierry Stump. Built to withstand the challenging conditions of the Southern Oceans, the Tortola offers both comfort and adventure, accommodating up to 13 passengers and providing sleeping arrangements for 8. Discover the elegance and resilience of this remarkable vessel through our online gallery, featuring stunning photos of the Tortola.

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.