TOP 30 Sunset sailing cruises in Massachusetts

20 results found

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.

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.

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 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!

Boston Sail Tours offers unforgettable sailing charters in the beautiful Boston Harbor. Our experienced captains will take you on a journey through the historic waters of Boston, showcasing iconic landmarks such as the USS Constitution and the Boston Tea Party Ships. Whether you are looking for a romantic sunset cruise or a fun-filled day out on the water with friends and family, Boston Sail Tours has the perfect charter for you. Come aboard our luxury sailing vessels and experience the thrill of sailing in one of America's most historic and picturesque harbors. Book your charter today at our location on 28 Constitution Road, Boston, Massachusetts, United States.

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.

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.

Massachusetts Bay Lines is a popular tourist attraction and travel agency located at 60 Rowes Wharf in Boston, Massachusetts. Offering a variety of scenic cruises and tours on the beautiful waters of Massachusetts Bay, this institution provides visitors with a unique and unforgettable way to experience the city's stunning skyline and historic landmarks from the water. Whether you're looking for a relaxing sightseeing cruise, a romantic sunset sail, or a fun harbor tour, Massachusetts Bay Lines has something for everyone. With knowledgeable guides, comfortable vessels, and breathtaking views, this institution is a must-visit destination for anyone looking to explore Boston by sea.

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.

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 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.

Experience the magic of Salem's maritime history with a sail on the renowned Fame of Salem Sailboat Tour. Located at 86 Wharf Street in Salem, Massachusetts, this top-rated travel agency offers a unique opportunity to step back in time and sail on a replica of the 1812 privateer Fame. Whether you're looking to help raise the sails or simply relax and enjoy the stunning views of Salem Sound, a sunset sail on the Fame is the perfect way to end your day in Salem. Listen to the roar of the sunset cannon as twilight descends over the water, creating a truly unforgettable experience.

The Schooner Thomas E. Lannon is a renowned travel agency located at 63 Rogers Street in the picturesque coastal town of Gloucester, Massachusetts. Specializing in unforgettable sailing experiences, the agency offers a variety of excursions aboard the historic Schooner Thomas E. Lannon, a beautifully restored 65-foot wooden vessel. Guests can enjoy breathtaking views of the Atlantic Ocean, learn about the rich maritime history of the area, and even participate in sailing the ship themselves. Whether you're looking for a romantic sunset cruise or a family-friendly adventure on the water, the Schooner Thomas E. Lannon promises a memorable and unique experience for all who come aboard.

The Liberty Fleet of Tall Ships Boston/Bahamas is a travel agency located at 67 Long Wharf in Boston, Massachusetts, United States. Under new ownership and with a new location at Fan Pier, the institution offers day sail adventures in Boston Harbor aboard the classic schooner, the Liberty Star. Experience the beauty of Boston from the water during a sunset cruise on a classic tall ship. The friendly and knowledgeable crew is always available to help, ensuring a relaxing and unforgettable sail. Guests can participate in raising the sails and enjoy a unique sailing experience around the harbor. Whether it's a bachelorette party or a leisurely cruise, the Liberty Fleet of Tall Ships offers a memorable and enjoyable way to see Boston. Don't miss out on this incredible opportunity to explore the city from a different perspective. Visit the Boston Travel Guide for more travel inspiration.

Welcome to The Landing at Long Wharf, Boston's premier waterfront bar located at 1 Long Wharf, Boston, Massachusetts 02110. Nestled right on the edge of Boston Harbor, The Landing offers an unparalleled experience with front-row seats to the city’s most spectacular events, including the iconic 4th of July fireworks. Book now to secure the best views of the celebrations from the water! Celebrate special occasions like Father’s Day with a unique twist by joining one of our themed cruises. Enjoy a day filled with laughter and dad jokes on the water, and make it a new family tradition with early booking discounts.