Boston · SAILING
Every trip has one free day too few. These 7 sailing trips justify the slot, priced and timed so you can decide in minutes and get back to the fun part.
Sail Salem Sound aboard the historic schooner Fame, help raise the sails, steer the boat, hear local stories, and enjoy a cannon shot.
“Absolutely recommend - the captain and crew were not only fun and engaging, but they were very kind and entertaining.”
Cruise Boston Harbor at sunset aboard the Northern Lights, with skyline views, light commentary, a full bar, and cannon fire from USS Constitution.
“The cruise was very nice. The food and drinks were good. But we have to wait for our food more time than we expected.”
Review of Boston’s two-hour sunset tall-ship cruise, with skyline views, drinks, crew tips, pricing, weather rules, and booking advice.
“Absolutely loved this experience aboard the Liberty Star. We had gorgeous city views from the water. The captain and deck hands were professional and informative yet extremely funny. Price was fair and we enjoyed the drink selection aboard.”
Sail Boston Harbor aboard the Adirondack III or IV, with skyline views, historic islands, friendly crew, drinks, and a gentle 90-minute ride.
“It was a wonderful boat ride! Crew was fun and friendly and it was a great experience!”
Sail Salem Sound aboard a historic schooner with sunset views, hands-on sailing, island scenery, and a full bar on this two-hour cruise.
“Relaxing cruise around the harbor. We took the sunset version and there were beautiful views. Small historic schooner, friendly crew. Makeshift bar on board, no real bathrooms and only accessible if you climb down a ladder and back up again so keep that in mind. Can get a bit chilly even in September so bring a jacket. If you have mobility issues this is not the cruise to book. Otherwise if you want a small boat experience where you are allowed to help (only if you want to) with some of the sailing tasks on board this will be right up your alley.”
Sail Salem Sound aboard the historic Schooner Fame, help raise the sails, hear privateer stories, and enjoy a relaxed 100-minute cruise.
“The crew was amazing. This was a wonderful excursion!”
Sail Buzzards Bay from Mattapoisett Harbor with a private captain, flexible routes, picnic options, and a quieter coastal setting.
“We had the most amazing sailing trip with Steve for my sisters bachelorette. He was so accommodating to all of our requests even modifying our trip due to weather to ensure we were safe and still able to go for a sail. We highly recommend Buzzards Bay Sailing Yacht Charters and Captain Steve!”
Pick a walk, a harbour or a dark street.
