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Sail Boston Harboraboard elegant schooners

Boston Sailboat Ride aboard the Adirondack Schooners

The best Boston sailboat ride in Boston Harbor aboard the Adirondack Schooners.
Duration: 1.5 or 2 hrs
Boat: Schooner Adirondack
Cost: Up to $74.20
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Our classic 1.5-hour or 2-hour Boston sailboat ride is a great afternoon boat cruise option and way to see the sights of Boston Harbor. There is no better way to sail Boston than by enjoying an experience aboard schooner Adirondack. An afternoon day sail aboard our classic sailboats is the most elegant day sailing in Boston you will find in the harbor. These boats are classically styled pilot schooners with long sleek lines, mahogany rails and classic finishes, offering a smooth and gentle Boston day sail experience with some speediness to boot. Boston sailing is great for families who want to get out and see the sights too! Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the joy of a leisurely harbor boat tour. So gather your friends and family and book your tickets now to experience one of the best things to do in Boston!
https://fareharbor.com/embeds/book/boston-sailing/items/26484/calendar/2025/05/?full-items=yes&flow=332335

Boston Sunset Sail on Schooner Adirondack

The best sunset sail in Boston Harbor aboard Schooner Adirondack
Duration: 2 hrs
Boat: Schooner Adirondack
Cost: Up to $101.76
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Experience a beautiful 2-hour Boston sunset sail on the water and see Boston’s iconic waterfront landmarks as the sun dips below the horizon. During this Boston sailing experience, guests can enjoy comfortable seating aboard the most elegant sailing yachts in town, our Adirondack schooners. These classically styled pilot schooners are the best option for a Boston sunset cruise when looking for fun things to do in Boston. Plus our Schooner Adirondack boats are the fastest and most elegant schooners in Boston Harbor, offering a smooth and gentle sailing experience and top-notch hospitality too. Enjoy a comfortable and relaxing ride with friends and family or for a special Boston date night. Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the ambiance of sunset sailing in Boston.
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Gloucester Sunset Sail on Schooner Adirondack

The best sunset sail in Gloucester aboard Schooner Adirondack
Duration: 2 hrs
Boat: Schooner Adirondack
Cost: Starting at $72.08
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Spend two unforgettable hours sailing Gloucester Harbor at sunset during the Gloucester Schooner Festival, one of New England’s signature maritime celebrations. This special cruise offers a unique opportunity to experience Gloucester while the harbor is filled with traditional schooners visiting for the festival. Throughout the sail, you’ll see many of these beautiful vessels underway around the harbor, creating a scene that only happens during this special weekend. As the sun begins to set, relax on the open deck and take in views of Gloucester’s historic coastline, lighthouses, beaches, and waterfront estates. The highlight of this cruise is simply being on the water during the festival itself. With schooners surrounding you, the evening light over Gloucester Harbor, and the city’s maritime history all around, this is a very different experience from a typical harbor cruise. Whether you’re visiting Gloucester for the festival or simply looking for a memorable evening on the water, this two-hour sunset sail offers a relaxed and scenic way to experience one of America’s most historic seaports.
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Schooner Adirondack Oyster Sail

The Boston Oyster Sail is a unique way to experience Boston from the water!
Duration: 2 hrs
Boat: Schooner Adirondack
Cost: Up to $76.32
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Join us for a Boston Oyster Sail! A Boston Harbor Sailing & Oyster Tour is a perfect blend of maritime adventure and culinary delight. Picture yourself aboard our classic sailboat, gliding across the waters of Boston Harbor with the city skyline as your backdrop. This is by far a unique experience to be had with your friends, family or loved one. Relish in the taste of freshly shucked oysters paired with mignonette, lemon, and hot sauce. Tours also offer champagne or crisp white wine to enhance the experience for purchase. Not only will you enjoy the delicious taste but will learn the history of farming and raising oysters and the importance of them to the local ecosystem. This Boston Oyster Sail is the perfect way to experience the harbor!
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Boston Harborfest Fireworks Sail

Celebrate Boston Harborfest aboard a classic yacht in Boston Harbor for a fireworks cruise.
Duration: 2 hrs
Boat: Schooner Adirondack
Cost: Up to $167.48
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It’s 4th of July in Boston and what better way to celebrate than with Boston Harborfest! Get your fourth of July week started with a bang and join Classic Harbor Line Boston for this fun family friendly event. During this Boston fireworks cruise aboard one of our Adirondack Schooners, enjoy a fun sightseeing cruise around Boston Harbor and see some of Boston’s most iconic sites. Wave to your fellow patriots on the shoreline as we pass by and get into position for an unobstructed view of the Harborfest fireworks on the water. Marvel at the spectacular fireworks display on this Boston Harborfest cruise and celebrate a memorable 4th of July in Boston. One complimentary drink is included with each ticket. So, if you are looking for Boston Harborfest events, then join us for a two hour cruise, followed by Harborfest Fireworks lighting up along Boston's Waterfront.
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Boston Labor Day Weekend Boat Tour with Fireworks

Enjoy a Labor Day Weekend boat tour with a Fireworks Cruise Aboard a Schooner Adirondack
Duration: 1.5 hrs
Boat: Schooner Adirondack
Cost: $95.40
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Looking for Boston events Labor Day Weekend? What better way to celebrate the end of summer than with a stellar Boston Labor Day Weekend Boat Tour for one of the best things to do in Boston for Labor Day! Join Classic Harbor Line Boston aboard Schooner Adirondack and enjoy Boston Harbor fireworks from waters of Boston Harbor. Our Schooners Adirondack offer the best Boston Labor Day Weekend views of the illuminated sky. This 1.5 hour cruise offers guests the opportunity to soak up the fireworks in Boston while relaxing on a comfortable open deck under the stars. Boston Harbor Fireworks are best seen from the water with unobstructed views in the harbor. Modeled after similar boats built in the 1890s but with modern upgrades, our boat rides are designed to provide space to accommodate our guests, ensuring a comfortable and quality experience for anyone who boards.
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U.S.S. Constitution Turnaround Boston Sail aboard the Adirondack Schooners

The best viewing of the U.S.S. Constitution Turnaround Boston maritime event aboard the Adirondack Schooners.
Duration: 2 hrs
Boat: Schooner Adirondack
Cost: Up to $171.72
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Boston on the 4th of July features an exciting series of Boston 4th of July events from fireworks shows to special viewings of the Boston USS Constitution Ship and more. For up-front seats to the USS Constitution Turnaround Boston, join Classic Harbor Line Boston aboard Schooner Adirondack for this special experience. This 2.5-3-hour long sail on July 4th to view the turnaround of the U.S.S. Constitution ship, the oldest (1797) actively commissioned naval vessel in the world, is sure to make memories that will last a lifetime. Experience 4th of July in Boston like you never have before aboard one of our Adirondack schooners, classic 1890s style pilot schooner, featuring comfortable seating and a brisk ride, as we are able to view the turnaround of the U.S.S. Constitution. You won't want to miss this truly unique and special program! During this annual event to celebrate our nation's birthday, the Boston U.S.S. Constitution will sail out into the harbor where she'll exchange a 21-gun salute with Castle Island's Fort Independence.
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Winthrop Fireworks Cruise on the Adirondack Schooners

The best Winthrop Fireworks Cruise in Boston Harbor aboard the classic Adirondack Schooners.
Duration: 3-3.5 hrs
Boat: Schooner Adirondack
Cost: Up to $284.08
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Sail Boston and join Classic Harbor Line Boston for a Winthrop fireworks cruise! This Boston sailing experience for the 4th of July in Boston is one not to be missed. Looking to skip sitting in traffic and dealing with crowds that go hand and hand with Boston 4th of July events? The Winthrop fireworks show aboard our classic boat, Schooner Adirondack, is a great alternative! Join us aboard one of our Adirondack schooners for a cruise to Winthrop to watch the fireworks. Then sail back to Boston under the gleaming night sky and see Boston’s iconic skyline lit up at night. This 3-hour event offers guests the opportunity to soak up Winthrop's fireworks display from an elegant and relaxing vantage point out on the water. Our Schooners Adirondack are brilliant pilot schooners modeled after similar boats built in the 1890s. With an open deck and comfortable seating, this Boston 4th of July cruise is sure to be an experience that will last a lifetime. In addition to a fantastic experience, this captivating Winthrop Fireworks Cruise will feature delicious, complimentary desserts and a complimentary drink of any kind with your purchase. If you’re looking for things to do in Boston for the 4th of July don’t wait! This experience often sells out in advance. Please note that the Winthrop Fireworks are weather permitting. We may not be able to raise sail for the fireworks due to crowding in the harbor. If time permits, we may do some sailing after the fireworks.
https://fareharbor.com/embeds/book/boston-sailing/items/26502/calendar/2024/12/?full-items=yes&flow=269877

Gloucester Schooner Fest Fireworks

Enjoin an evening of enchanting fireworks!
Duration: 1.5 hrs
Boat: Schooner Adirondack
Cost: Starting at $114.48
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Join Schooner Adirondack III for a special Gloucester Schooner Festival fireworks sail and experience New England’s maritime tradition from the deck of an authentic 80-foot pilot schooner. As night falls, watch Gloucester Harbor come alive as a fleet of beautiful schooners gathers on the water, creating the perfect backdrop for an unforgettable evening. Enjoy a complimentary drink and unobstructed waterfront views as the festival fireworks light up the harbor and reflect across the water! Feel the breeze, take in the sights, and settle in for an authentic sailing experience that caputres the spirit of Gloucester and its rich maritime heritage. It's a magical night on the water and a celebration you won't want to miss! The crew offers an engaging, authentic sailing experience for guests of all interests. Don't miss out on this special event with us!
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The best sailing in Boston Harbor

Sail Boston with Classic Harbor Line Boston aboard our classic Adirondack schooners. Boston sailing is a well known local and tourist activity and a great way to see the sights of Boston, including the best sunsets in Boston, while relaxing on a boat. Sail boat tours are the perfect way to do some Boston Harbor sightseeing with friends, family or colleagues. Join Classic Harbor Line Boston alongside our professional crew and take to the waters to sail Boston this year!

Let our amazing crew dazzle you with their sailing skills and top-notch customer service as our sailboat in Boston Harbor glides along the waterfront. Sailing in Boston is fun, but sailing and sightseeing is the most wonderful way to experience Beantown. Our Boston Harbor tours and Boston Harbor Cruises are sure to give you an experience you won’t forget.

Sail Boston

Looking to do some Boston Harbor sightseeing? These Boston boat tours will sail past Boston’s historic waterfront to see the U.S.S. Constitution, Fort Independence (named by George Washington), Marriott Custom House Tower, U.S.S Cassin Young, and see the steeple of the Old North Church in Boston’s North End. Our sail boat tours will show you the Boston skyline and local Islands, which are a must see while visiting (or if you just need an escape from the city).   Enjoy some Boston sailing, and the historic sites with a glass of wine or Champagne in hand aboard our Adirondack schooners.

We are known as a top rated sailboat for a Boston sunset sail! We not only offer the most premium sailing experience in Boston, but also have 5 star reviews for our exceptional service.  Our schooner sails are sure to show you the town in the most unique and authentic way. So don’t miss out on our sail boat sunset cruise! Sail Boston with us and let us host you for this unforgettable experience.

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