TOP 30 Family sailing vacations in Massachusetts

28 results found

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.

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.

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.

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.

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.

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.

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.

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 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.

The Cutty Sark is a charming lodging institution located at 396 Old Wharf Road in Dennis, Massachusetts. This historic building offers a cozy and comfortable stay for guests looking to experience the beauty of Cape Cod. The Cutty Sark features well-appointed rooms, a friendly staff, and a convenient location near the beach and local attractions. Whether you're visiting for a weekend getaway or a longer vacation, The Cutty Sark is the perfect place to relax and unwind.

The Colony of Wellfleet is a unique lodging institution located at 640 Chequessett Neck Road in Wellfleet, Massachusetts, United States. Originally designed and built in 1948 by architects Nathaniel Saltonstall and Oliver P. Morton, this institution was known as the Mayo Hill Colony Club, serving as a private club and art gallery for artists and patrons. In 1963, Loris and Eleanor Stefani acquired the cottages and transformed them into a hotel, adding their own creative touches and artwork to create The Colony as it is known today. Managed by their son Jeffrey and his wife Mihae since 2019, The Colony offers a truly special summer retreat in the Northeast. The Colony of Wellfleet features 10 Bauhaus-style cottages overlooking Wellfleet harbor and bay, each designed for elegant functionality and furnished with pieces by leading modernists. Guests can enjoy reserved beach space, golf, tennis, pickleball, sailing lessons, and more at the club. The cafe offers coffee, pastries, lunch, and drinks with stunning views. Flexible membership options are available for guests.

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.

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.

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.

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!

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!

Crescent Yacht Club is a prestigious sailing institution located at 30 Ferry Street in Haverhill, Massachusetts, United States. With a rich history dating back to its founding, Crescent Yacht Club offers a range of programs and events for sailing enthusiasts of all levels. The club's facilities include a marina, clubhouse, and sailing school, providing members with access to top-notch amenities and resources. Whether you're a seasoned sailor or just starting out, Crescent Yacht Club is the perfect place to enjoy the sport of sailing in a welcoming and inclusive environment.

Chequessett Yacht & Country Club is a health institution located at 680 Chequessett Neck Road in Wellfleet, Massachusetts. This club offers a variety of activities including Golf, Tennis, Pickleball, and Sailing, all while overlooking the beautiful Wellfleet Harbor. The club features a nine-hole semi-links golf course, Novo Pro Turf tennis courts, and a Waterfront Beach Club. They also have venue spaces for waterfront weddings and special events, as well as a restaurant serving breakfast and lunch with a view of the 9th hole or Wellfleet Bay. Families can register their children for a summer program filled with various activities. Non-members can play the course for a fee, and riding carts are available for members during the winter months. Come enjoy the amenities and create lasting memories at Chequessett Yacht & Country Club in Cape Cod.

Bass River Yacht Club is a prestigious institution located at 22 Frothingham Way in Yarmouth, Massachusetts, United States. With a rich history dating back to its founding, the club offers a range of amenities and activities for members to enjoy. From sailing regattas to social events, the Bass River Yacht Club provides a vibrant community for boating enthusiasts of all ages. The club's prime location on the Bass River offers stunning views and access to some of the best sailing waters in the region. Whether you're a seasoned sailor or a newcomer to the sport, the Bass River Yacht Club welcomes all who share a passion for the sea and the camaraderie of fellow members.

Welcome to Diamond Key Real Estate, your premier destination for all your real estate needs in Massachusetts, New Hampshire, and Florida. Located at 780 Main Street, Haverhill, Massachusetts 01830, our dedicated team is here to provide you with the best real estate search experience for homes, condos, land, and foreclosure properties. Our website is designed with you in mind, offering an easy-to-use platform that is updated every 15 minutes by the official Realtor®'s database. Whether you are looking to buy or sell, you can save your searches and receive daily email alerts about new listings, price changes, sold data, and market reports. Our Interactive Map Search feature allows you to view properties on a map or refine your search by drawing boundaries around your desired area.