Best 7 Sailing in Boston , Massachusetts
Save 10% Free Cancellation Sightseeing Day Sail around Boston Harbor
Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport distri…
Free Cancellation Classic Tall Ship Cruise in Boston Harbor
Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the city streets and enjoy some quality time out on the water wi…
Free Cancellation Sunset Sailing Cruise on a Tall Ship in Boston Harbor
If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and rela…
Free Cancellation Harbor Sail Aboard the Tall Ship Denis Sullivan
Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views…
Free Cancellation Pastries & Prosecco Aboard a Tall Ship in Boston Harbor
What a way to celebrate the weekend! Enjoy a lovely two hour sail on Boston Harbor with unbeatable views of the city. Your ticket includes complimentary coffee and fresh-baked pastries from the incomparable Flour Bakery …
Free Cancellation Night Sail in Boston Harbor
Enjoy a night sail around Boston Harbor aboard a classic sailboat. See the city skyline and iconic buildings at night and enjoy the glittering lights of the city. Sit back and relax as the crew raises sail. This is a pop…