TOP 10 Best Luxury sailing vacations in martha's vineyard in Massachusetts

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.

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.

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.

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.

Local Tide Charters is a premier fishing and boating charter service located at 61 Crocker Drive in Edgartown, Massachusetts. Our experienced captains and crew are dedicated to providing unforgettable experiences on the water, whether you're looking to reel in a big catch or simply enjoy a relaxing cruise along the beautiful coastline. With a variety of charter options available, including deep sea fishing trips, sunset cruises, and private charters, Local Tide Charters is the perfect choice for both seasoned anglers and beginners alike. Join us for an adventure on the local tides and create memories that will last a lifetime.

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.

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.

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.

Island Time Charters is a premier charter service located at 19 Owen Park Way in Tisbury, Massachusetts. With a prime location on Martha's Vineyard, our experienced captains and crew are dedicated to providing guests with unforgettable experiences on the water. Whether you're looking to explore the beautiful coastline, fish for your dinner, or simply relax and enjoy the stunning views, Island Time Charters has a variety of options to suit your needs. Join us for a day of adventure and relaxation on the water with Island Time Charters.

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.