Filters
When you want to ?
Price Range
Rating
Clear Filter
Sailing in Boston | Tours & Experiences
100
Sail into History: Schooner Fame's Unforgettable Salem Adventure
Schooner Fame Sailing Tour offers a hands-on sailing adventure aboard a replica War of 1812 privateer. Raise sails, steer the boat, and hear tales of Salem's maritime past. Relax and enjoy scenic views of historic forts and lighthouses. This family friendly tour provides a unique blend of history and scenic beauty on the water.
Schooner Fame Sailing Tour offers a hands-on sailing adventure aboard a replica War of 1812 privateer. Raise sails, steer the boat, and hear tales of Salem's maritime past. Relax and enjoy scenic views of historic forts and lighthouses. This family friendly tour provides a unique blend of history and scenic beauty on the water.
From
$ 45
120
Sail into History: Schooner Yacht Adventure in Salem, MA
Experience Salem's maritime history aboard the Malabar X, a beautifully restored schooner yacht. This vessel is a winner of the 1930 and 1932 Newport to Bermuda race. Enjoy harbor views, and onboard refreshments. Participate in sailing or relax, suitable for all ages.
Experience Salem's maritime history aboard the Malabar X, a beautifully restored schooner yacht. This vessel is a winner of the 1930 and 1932 Newport to Bermuda race. Enjoy harbor views, and onboard refreshments. Participate in sailing or relax, suitable for all ages.
From
$ 55
180
Sail Away to Fishers Island: Private Yachting from New London!
Experience a private sailing trip around Fishers Island from New London, CT. Enjoy gorgeous views on a relaxing yacht, with options for swimming. Trips are approximately 3-4 hours. Limited to 4 people, larger groups are available on request. Discover the beauty of the harbor and create lasting memories.
Experience a private sailing trip around Fishers Island from New London, CT. Enjoy gorgeous views on a relaxing yacht, with options for swimming. Trips are approximately 3-4 hours. Limited to 4 people, larger groups are available on request. Discover the beauty of the harbor and create lasting memories.
From
$ 720
120
Boston Harbor Bliss: Pastries, Prosecco & Panoramic Views!
Pastries and Prosecco in Boston Harbor offers a delightful two-hour sail with city views. Enjoy complimentary pastries from Flour Bakery + Cafe and optional $5 mimosas. This brunch sail, perfect for a relaxing weekend, requires no sailing skill, focusing on leisure and scenic enjoyment on Boston's iconic harbor.
Pastries and Prosecco in Boston Harbor offers a delightful two-hour sail with city views. Enjoy complimentary pastries from Flour Bakery + Cafe and optional $5 mimosas. This brunch sail, perfect for a relaxing weekend, requires no sailing skill, focusing on leisure and scenic enjoyment on Boston's iconic harbor.
From
$ 75
90
Newport Sunset Sail: Aboard the Historic Schooner Adirondack
Experience Newport's charm on the Schooner Adirondack. This 1.5-hour sunset sail offers iconic views of lighthouses, mansions, and classic vessels along Narragansett Bay. Relax and soak in the sights from this classic sailboat. Perfect for a memorable evening in Newport, skill level is beginner-friendly.
Experience Newport's charm on the Schooner Adirondack. This 1.5-hour sunset sail offers iconic views of lighthouses, mansions, and classic vessels along Narragansett Bay. Relax and soak in the sights from this classic sailboat. Perfect for a memorable evening in Newport, skill level is beginner-friendly.
From
$ 68
120
Maine's Luxurious Catamaran Sailing: Kennebunkport Coastal Cruise
Luxury Catamaran Sailing Charters in Maine offers a stable, comfortable, and luxurious sailing experience on a 44-ft catamaran yacht. Enjoy multiple seating areas, including trampolines, perfect for relaxing and sightseeing. Ideal for romantic sunset cruises, cocktail parties, or leisurely sails past lighthouses. Bring your own refreshments for a flawless adventure.
Luxury Catamaran Sailing Charters in Maine offers a stable, comfortable, and luxurious sailing experience on a 44-ft catamaran yacht. Enjoy multiple seating areas, including trampolines, perfect for relaxing and sightseeing. Ideal for romantic sunset cruises, cocktail parties, or leisurely sails past lighthouses. Bring your own refreshments for a flawless adventure.
From
$ 135
90
Newport Sailing: Classic Schooner Sightseeing Adventure!
Newport Afternoon Sightseeing Sail offers a relaxing cruise on Narragansett Bay aboard the Schooner Madeleine. Enjoy iconic views of lighthouses, mansions, and bridges. Bring your own snacks and purchase drinks onboard for a delightful experience suitable for all. Perfect for locals and visitors alike!
Newport Afternoon Sightseeing Sail offers a relaxing cruise on Narragansett Bay aboard the Schooner Madeleine. Enjoy iconic views of lighthouses, mansions, and bridges. Bring your own snacks and purchase drinks onboard for a delightful experience suitable for all. Perfect for locals and visitors alike!
From
$ 57
90
Sail into History: Newport's Breathtaking Schooner Adirondack Experience
Newport Sightseeing Day Sailing Experience on Schooner Adirondack offers a scenic 1.5-hour sail around Newport Harbor, showcasing iconic sights, bridges, and lighthouses. This sailing adventure allows guests to relax and enjoy the beautiful coastal views, perfect for those seeking a leisurely and picturesque experience on the water.
Newport Sightseeing Day Sailing Experience on Schooner Adirondack offers a scenic 1.5-hour sail around Newport Harbor, showcasing iconic sights, bridges, and lighthouses. This sailing adventure allows guests to relax and enjoy the beautiful coastal views, perfect for those seeking a leisurely and picturesque experience on the water.
From
$ 57
0
Boston Harbor Sailing: A Sightseeing Schooner Adventure
Experience Boston Harbor on a classic schooner! The Sightseeing Day Sail offers 1.5 or 2-hour cruises past iconic landmarks. Relax with beverage service, enjoy the views, and learn harbor history from the crew. Guests can bring their own picnic for a leisurely experience on the water, suitable for families and friends.
Experience Boston Harbor on a classic schooner! The Sightseeing Day Sail offers 1.5 or 2-hour cruises past iconic landmarks. Relax with beverage service, enjoy the views, and learn harbor history from the crew. Guests can bring their own picnic for a leisurely experience on the water, suitable for families and friends.
From
$ 67
0
Set Sail on the Liberty Star: A Classic Boston Harbor Cruise!
The Classic Tall Ship Sightseeing Cruise of Boston Harbor offers a unique sailing experience aboard the Liberty Star. Enjoy scenic city views, optional Mimosa/Brunch sail, and historical insights from the crew. Bring your snacks and immerse yourself in the maritime charm of Boston. Relaxing adventure on the water!
The Classic Tall Ship Sightseeing Cruise of Boston Harbor offers a unique sailing experience aboard the Liberty Star. Enjoy scenic city views, optional Mimosa/Brunch sail, and historical insights from the crew. Bring your snacks and immerse yourself in the maritime charm of Boston. Relaxing adventure on the water!
From
$ 35
90
Newport Sunset Sail: A Classic Coastal Cruise
Newport Sunset Sail on Classic Sailboat offers a serene 1.5-hour journey through Narragansett Bay. Witness iconic sights, historic lighthouses, and opulent mansions from a unique vantage point. Guests can bring light snacks to enjoy during the sail, enhancing the relaxing experience. A perfect way to end the day!
Newport Sunset Sail on Classic Sailboat offers a serene 1.5-hour journey through Narragansett Bay. Witness iconic sights, historic lighthouses, and opulent mansions from a unique vantage point. Guests can bring light snacks to enjoy during the sail, enhancing the relaxing experience. A perfect way to end the day!
From
$ 68
120
Breathtaking Boston Sunset Sail: Unwind on the Water
Boston Harbor Sunset Sail Tour: Experience a serene evening aboard a classic schooner, Adirondack III or IV. Enjoy smooth sailing, waterfront views, and top-notch service as the sun sets over Boston. A relaxing escape from city life with stunning photo opportunities.
Boston Harbor Sunset Sail Tour: Experience a serene evening aboard a classic schooner, Adirondack III or IV. Enjoy smooth sailing, waterfront views, and top-notch service as the sun sets over Boston. A relaxing escape from city life with stunning photo opportunities.
From
$ 82
120
Boston Sunset Sail: Unforgettable Tall Ship Cruise
Sunset Sailing Cruise on a Tall Ship in Boston Harbor offers stunning skyline views as you relax on a classic tall ship. Enjoy the twilight, purchase drinks (including local Boston beers), and feel free to bring snacks. Chat with the crew about landmarks. A unique, relaxing escape on the water.
Sunset Sailing Cruise on a Tall Ship in Boston Harbor offers stunning skyline views as you relax on a classic tall ship. Enjoy the twilight, purchase drinks (including local Boston beers), and feel free to bring snacks. Chat with the crew about landmarks. A unique, relaxing escape on the water.
From
$ 68
90
Newport Sailing: Mimosa Morning on the Schooner Madeleine!
Enjoy a 'Morning Mimosa Sightseeing Sail' aboard Schooner Madeleine. This 1.5-hour sail showcases Newport's waterfront, including the Newport Bridge, historic lighthouses, and mansions. Relax with a mimosa (available for purchase) while viewing iconic sights. A perfect blend of luxury and local beauty!
Enjoy a 'Morning Mimosa Sightseeing Sail' aboard Schooner Madeleine. This 1.5-hour sail showcases Newport's waterfront, including the Newport Bridge, historic lighthouses, and mansions. Relax with a mimosa (available for purchase) while viewing iconic sights. A perfect blend of luxury and local beauty!
From
$ 57