Top 30 Best Sailing holidays in Massachusetts

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.

Cape Cod Catamaran Sailing Charters is a travel agency located at 255 Commercial Street in Wellfleet, Massachusetts, United States.

Captain Curley's Sailing Charters is a premier travel agency located at 255 Commercial Street in Wellfleet, Massachusetts.

Moment Sailing Adventures is located at 16 MacMillan Pier in Provincetown, Massachusetts, offering deluxe private captained day sailing charters.

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.

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.

Mad Max Sailing Adventures offers thrilling and unforgettable experiences on the water in Edgartown, Massachusetts. Our expert crew will take you on a high-speed sailing adventure, where you can feel the wind in your hair and the salt spray on your skin.

Buzzard's Sailing School Inc is a premier sailing school located at 99 South Road in Bourne, Massachusetts, United States.

Sailing @ CD Recreation is a premier sailing institution located at 59 Heritage State Park - Bicentennial Park Trail in Fall River, Massachusetts.

Sail Buzzards Bay is a premier sailing institution located at 101 Main Street in Fairhaven, Massachusetts. Our facility offers top-notch sailing programs for all skill levels, from beginners to advanced sailors.

Wild Harbor Sailing is a premier sailing institution located at 386 Grove Street in Falmouth, Massachusetts, United States.

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.

Defiance Sail Charters is a premier travel agency located at 211 East Main Street in Gloucester, Massachusetts, United States.

Sail The Vineyard is a travel agency located in Tisbury, Massachusetts, United States. Situated at 1 Lagoon Pond Road #1923, Vineyard Haven, Massachusetts 02568, the agency offers unique and exciting sailing experiences around Martha's Vineyard.

Crimson Sailing Academy is a prestigious institution located at 45 Memorial Drive in Cambridge, Massachusetts, United States. The academy offers top-notch sailing education and training programs for students of all skill levels.

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.

Catboat Charters is a premier travel agency located at 1 Dock Street in Edgartown, Massachusetts.

Located at 10 MacMillan Pier in Provincetown, Massachusetts, the Schooner Hindu and the Cutter Bloodhound travel agency offers unique and exciting sailing experiences.

The Schooner Thomas E. Lannon is a renowned travel agency located at 63 Rogers Street in the picturesque coastal town of Gloucester, Massachusetts.

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.

Liberte, The Schooner is a renowned travel agency located at 227 Clinton Avenue in Falmouth, Massachusetts, United States.

Laura Jay Charters is a premier travel agency located at 25 Ed Moffitt Drive in Sandwich, Massachusetts. Specializing in luxury yacht charters, they offer unforgettable experiences on the water for their clients.

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.

The New Bedford Yacht Club is a prestigious institution located at 208 Elm Street in Dartmouth, Massachusetts, United States.

Wellfleet Marine is a premier store located at 25 Holbrook Avenue in Wellfleet, Massachusetts. Specializing in all things marine-related, this institution offers a wide range of products and services for boating enthusiasts and ocean lovers alike.

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.

The Lynn Yacht Club is a prestigious institution located at 86 Lynnway in Lynn, Massachusetts, United States. Established in [year], the club is renowned for its vibrant community of boating enthusiasts and maritime aficionados.

Wequaquet Lake Yacht Club is a prestigious sailing club located at 150 Annable Point Road in Barnstable, Massachusetts.

Vineyard Ferries is a transportation institution located at 1 Cowdry Road in Falmouth, Massachusetts, United States. If you're planning to travel to Martha's Vineyard, Vineyard Ferries offers schedules from all ferry lines servicing the island.

Welcome to the Town River Yacht Club, a premier destination for boating enthusiasts and social gatherings located in the heart of Quincy, Massachusetts.