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TOP 30 Sailing trips in Massachusetts
30 results found
Search for local businesses, places and services near you
Sail When And If
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.
Frayed Knot Sailing Charters
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.
Sail Cape Cod Provincetown
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
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
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
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!
Sailing Martha's Vineyard
Sailing Martha's Vineyard is located at the Menemsha jetty dinghy dock and Basin Road in Chilmark, Massachusetts, United States. The institution offers ultimate sailing experiences aboard a custom-built mega-yacht designed for island passage-making. With a variety of short, protected sails, guests can glide across Vineyard Sound and explore the remote Elizabeth Islands. For the more adventurous, longer ocean sails around the island and beyond are also available. The institution prides itself on providing a range of sailing options, from 1-hour sails to overnight trips, all at affordable prices. With a focus on direct communication and booking, guests can enjoy savings on repeat visits. The experienced crew, led by Captain Nick and first mate Charlie, ensures a safe and enjoyable sailing experience for all guests.
Mad Max Sailing Adventures
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. Whether you're a seasoned sailor or a first-timer, our trips are perfect for anyone looking for a unique and exciting way to explore the beautiful waters of Martha's Vineyard. Join us at 25 Dock Street for an unforgettable sailing experience with Mad Max Sailing Adventures.
Endeavor Sailing Excursions
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.
SV Dream Escapes LLC
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.
Cliff Lodge Bed & Breakfast
Located at 9 Cliff Road in Nantucket, Massachusetts, the Cliff Lodge Bed & Breakfast offers a leisurely ambiance and delightful charm to its guests. Originally built in 1771 as a whaling master's home, this historic inn is just a short walk from the ferry and the town, making it a perfect place to experience the beauty and enchantment of Nantucket. Returning visitors often consider Cliff Lodge as their home-away-from-home, appreciating the easy elegance of island life and the exceptional hospitality provided by the hostess and staff. The rooms offer a nice view and the breakfasts, which vary daily, are a highlight for guests. Despite COVID-19 limitations, the inn has managed to maintain its inviting common areas and outdoor spaces.
The Cottages at Nantucket Boat Basin
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.
CheapCruises.com
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!
Island Girl Excursions
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
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
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.
Maritime Heritage Charters
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.
Paramount Vacations - Melanie Richards
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 Planners
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!
Newburyport Yacht Club
Located at 300R Merrimac Street in Newburyport, Massachusetts, the Newburyport Yacht Club has been a prominent boating club since its establishment in 2001. Situated on the Merrimack River, the club offers deepwater dockage and is close to prime sport fishing and sailing areas. With 192 slips on three docks, the marina provides a convenient location for boaters. The Club House features amenities such as a pool, parking, and restrooms with hot showers. Social events are held throughout the summer, including cookouts, live music, and boat trips. Memberships are available for purchase, as well as transient dockage options. The club offers seasonal memberships with access to summer slips and winter land storage. With a range of activities for every family member, the Newburyport Yacht Club is a welcoming and inclusive boating community.
The National Charter 957
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.
The Jaguar Path
The Jaguar Path is a transformative school located at 70 Kemble Street in Lenox, Massachusetts, United States. Founded by Ray and Nina Crist, The Jaguar Path offers unique trainings in Shamanism, Yoga, and Tai Chi that bridge ancient wisdom with the modern world. Through their profound insights into shamanism, Ray and Nina reveal a path of enlightenment that resonates in everyday life, offering guidance to navigate the complexities of the world with clarity and purpose. At The Jaguar Path, students can master their energy and step into their optimal way of being. The institution also offers exclusive retreats to Greece in the summer, where participants can explore ancient temples, sailing trips, and luxury charters.
Martha's Vineyard Ocean Academy
Martha's Vineyard Ocean Academy is a unique institution located at 112 Main Street, Tisbury, Massachusetts, United States. We offer sailing voyages that foster purpose, happiness, and resilience in individuals of all ages. Our participants experience increased confidence in their interactions with others, develop a deeper connection with nature, and learn mariner skills while bonding with staff and peers in a fun, supportive, and inclusive community. Our groundbreaking curriculum, developed in collaboration with the University of New Hampshire School of Social Work, ensures the highest quality of learning and personal development for children. Participants aboard our ship benefit from a transformative experience that is often described as "life-changing."
True Blue Waters
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.
Vineyard Ferries
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. For the best bike rental experience on the island, they recommend their preferred partner, All Star Bike Rentals, conveniently located near the ferries. The schedules for departures from Woods Hole to Martha's Vineyard and vice versa are provided, along with fares from the Steamship Authority. Additional ferry options from New Bedford and Hyannis to Martha's Vineyard are also available. Seastreak and Hy-Line Cruises offer alternative ferry services with different rates. Vineyard Fast Ferry provides fast and convenient travel options with various rates based on age and peak days. For those looking to explore Martha's Vineyard, car rentals and bike rentals are available on the island. Flights to Martha's Vineyard can also be arranged from local airports. Vineyard Ferries is a valuable resource for travelers planning trips to Martha's Vineyard and Nantucket, along with other ferry schedule resources. Please note that Vineyard Ferries is not affiliated with specific ferry companies mentioned. Happy sailing!
Charlestown Navy Yard
Discover the Historic Charlestown Navy Yard Nestled in the heart of Boston, Massachusetts, at 3rd Street, the Charlestown Navy Yard stands as a testament to America's naval legacy and innovation. As a premier tourist attraction, this site invites you to step back in time and explore the pivotal role it played in shaping the nation's maritime history.
Marianna's Marina
Welcome to Marianna's Marina, your premier storage destination on the picturesque banks of the Merrimack River in Haverhill, Massachusetts. Conveniently located at 72 Coffin Avenue, our family-friendly marina has been proudly serving the Merrimac Valley boating community since 1996. Formerly known as "Kaz" Marina, we have remained locally owned and operated for over 26 years, offering a safe and welcoming environment for all. Marianna's Marina is ideally situated for freshwater enthusiasts, with the Merrimack River offering a diverse range of fishing opportunities. From bass and carp to trophy panfish like large black crappie and big redbreast sunfish, the river is teeming with aquatic life. For those venturing towards the lower sections, striped bass and American shad await avid anglers during their seasonal runs.
Bakers Island Light Station
Welcome to Bakers Island Light Station Nestled off the coast of Salem, Massachusetts, on the picturesque Bakers Island, the Bakers Island Light Station stands as a beacon of history and natural beauty. Managed by the Essex National Heritage Commission (Essex Heritage), this historic site invites you to explore its rich heritage and breathtaking surroundings.
Shoolman Nature Preserve
Welcome to Shoolman Nature Preserve, a hidden gem located at 184-240 New Bedford Road, Rochester, Massachusetts. This serene park is a nature lover's paradise, offering a peaceful escape into the beauty of fields and pine forests along the Mattapoisett River. Once a family farm known as "Oldfield," the property is now a haven for birds and explorers alike, thanks to the generous donation by the Shoolman family and the dedicated efforts of the Mattapoisett Land Trust and the Rochester Land Trust. At Shoolman Preserve, you can embark on a leisurely walk along our flat, easy trails that wind through hayfields, forests, and freshwater wetlands. Whether you're a bird enthusiast, a nature photographer, or simply someone seeking a breath of fresh air, you'll find plenty to admire. Look out for the diverse birdlife, including titmice, chickadees, bobolinks, and meadowlarks, as well as deer, foxes, wood frogs, and box turtles.
Tinkhamtown Woodlands
Welcome to Tinkhamtown Woodlands, a serene sanctuary nestled at 29 Long Plain Road in the heart of Mattapoisett, Massachusetts. As part of the expansive Mattapoisett River Reserve, this enchanting park offers visitors a unique opportunity to explore over 100 acres of pristine forests and wetlands, all while contributing to the protection of clean drinking water for thousands of local residents. Tinkhamtown Woodlands is a treasured property of the Buzzards Bay Coalition, a nonprofit organization dedicated to preserving the natural beauty and ecological integrity of Buzzards Bay and its watershed. This area is also supported by the Mattapoisett Land Trust, which has been enriching the community's quality of life since 1974 through land conservation.
- Sailing trips in Boston
- Sailing trips in Edgartown
- Sailing trips in Falmouth
- Sailing trips in Gloucester
- Sailing trips in Hanover
- Sailing trips in Haverhill
- Sailing trips in Lenox
- Sailing trips in Nantucket
- Sailing trips in Newburyport
- Sailing trips in Provincetown
- Sailing trips in Salem
- Sailing trips in Sudbury
- Sailing trips in Taunton
- Sailing trips in Tisbury
- Sailing trips in Wakefield
- Sailing trips in Wellfleet
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