BOSTON · BOSTON SAILING AND TALL SHIP TRIPS
Under sail the harbor slows down and the narration stops. The 12 below cover the schooners, the day sails and the yacht charters, compared on time on the water, group size and what the fare includes.
Spend about 90 minutes aboard the Liberty Star with Captain Fredo and crew members Jess and Max. Expect open-air harbor views, light commentary, drinks for purchase, and possibly a chance to help raise the sails. The route depends on wind and weather.
“Amazing! Perfect ship, perfect crew. We had a great time! Captain Freddo was great! And they serve alcohol so that's a plus!”
Join Captain Mike and the crew of the replica privateer schooner Fame from Pickering Wharf in downtown Salem. During this roughly 1-hour-40-minute sail, you can help raise the sails, steer, hear stories about Salem Sound, and watch the cannon fire. Children under five are not allowed.
“The crew so nice, let you steer schooner and very informative. Had a great time today! Definitely recommend this excursion.”
Spend two hours aboard the classic Northern Lights, a 115-foot yacht with indoor seating, open decks, a bar, and six bathrooms. See Castle Island, the inner harbor, Boston’s skyline, and the USS Constitution’s sunset cannon fire while the captain provides light commentary.
“Food was good, bit pricey and limited options but alright. The viewing deck was spacious and clean. Good customer service.”
Set sail from Rowes Wharf aboard Schooner Adirondack III or IV for 1.5 or 2 hours. Expect a relaxed harbor trip past the Seaport, Fan Pier, Fort Independence, Spectacle Island, and Long Island. Crew members answer questions, while a card-only bar serves drinks.
“Erick the captain was great and you can see he has lots of experience. Claire and Adam were very kind.”
Join Liberty Fleet of Tall Ships at Fan Pier Marina for a two-hour sunset sail aboard a traditional Boston tall ship. Expect skyline and harbor views, a relaxed crew, drinks from the galley bar, and occasional chances to help with the sails. Captains Fredo and the deck crew have earned special praise for their warm, playful service.
“Really nice cruise around Boston Harbor. The crew was awesome and the skyline views were incredible!”
Sail Boston Harbor aboard the classic Schooner Adirondack III or IV for two hours at sunset. From Rowes Wharf, you’ll pass the Fish Pier, Castle Island, Fan Pier, the Charleston Navy Yard, and Inner Harbor Islands while the crew shares local history. Drinks are available for purchase, but not included.
“Very enjoyable and the captain and crew were wonderful.”
Board a classic schooner at Fan Pier Marina for a 90-minute Boston Harbor sail. The crew raises the sails, answers questions, and may invite you to help with the lines or wheel. Bring snacks, buy a local beer or cocktail, and enjoy skyline, island, airport, and harbor views.
“Well worth the price. Great boat. Excellent, friendly and skilled crew. Would definitely recommend and would do it again.”
Join the crew of the Adirondack III or IV for a 90-minute or two-hour Boston Harbor sail. You’ll pass the Aquarium, Fish Pier, Castle Island, Navy Yard, and Inner Harbor Islands while the crew answers questions. Bring a picnic, a photo ID, and a light jacket.
“It was a very relaxing sailing experience. It wasn’t real windy, the boats movements were a gentle swaying motion most of the time. Only occasionally did it move up and down but it wasn’t very long. Some passengers were worried about motion sickness but they were all fine. No one got sick.”
Board a beautifully maintained classic schooner at 10 Blaney Street in Salem for a two-hour sail with Captain Seth and crew members such as Kos and Kate. Help raise the sails, hear stories about the vessel and nearby islands, enjoy Salem Sound views, and buy drinks from the onboard bar.
“Crew was great. Beautiful night and a beautiful boat. Had a gin and tonic and helped with the sails. Would highly recommend”
Spend about two hours aboard the Schooner Adirondack II or III, sailing from Rowes Wharf past Fan Pier, harbor islands, Castle Island, and Fort Independence. This is not a narrated cruise, but crew members such as Dante, Charlie, and Claire can answer questions while you enjoy the sunset and buy drinks by credit card.
“It was a wonderful experience! The crew was very interactive with everyone and so accommodating! It was as if you had known them for a long time. I would highly recommend this excursion if you ever visit Boston.”
Spend two hours aboard Liberty Star with the Liberty Fleet of Tall Ships, sailing from Fan Pier Marina around Boston Harbor. You can help raise the sails, try steering, and chat with crew such as Captain Freido, Jess, and Max. Bring snacks, buy Boston beer onboard, and dress warmly for the water.
“Captain Jonathan and his crew were wonderful. They're stories and the ability to help bound with a raising. The sales made the experience truly amazing”
Board the gaff-rigged Schooner Fame at Pickering Wharf Marina for a 100-minute Salem Sound cruise. Captain Mike and crew members John and Ella may invite you to raise the sails, take the tiller, and hear about privateering, forts, lighthouses, and Salem’s busy maritime past.
“Fantastic tour, we had a great time!! The Captain and crew were great, something very relaxing about cruising across the water with no engine noise!! My young daughter had a blast!!”
Pick a walk, a hull, a plate or a ghost story.
