Boston Waterfront
Group Activities

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Our most recommended Boston Waterfront Group Activities

Boston: Downtown Harbor Sailing Cruise

1. Boston: Downtown Harbor Sailing Cruise

Experience Boston like never before on board the 80-foot pilot schooner Adirondack III, and enjoy a smooth sailing, with some invigorating speed to boot. Within minutes of leaving dock, you’ll forget the distractions of life on land as you experience the joy of a sailing adventure. Cruise past landmark attractions, such as the Boston Fish Pier, Moakley Federal Courthouse at Fan Pier, and Castle Island. Drift past the Inner Harbor Islands and see the historic Charleston Navy Yard. Look out for the green oasis of Waterfront Park and the home to hundreds of marine critters, including sharks and sea turtles, at New England Aquarium. Your knowledgeable captain and crew will be on hand to answer questions about the sights and history of Boston Harbor and its surrounds, from interesting facts to old-time legends. Wines and local micro beers are available to purchase on board, while complimentary soda and water will keep you hydrated along the way.

Boston: Champagne City Lights Cruise 1920s Commuter Yacht

2. Boston: Champagne City Lights Cruise 1920s Commuter Yacht

Sit back and relax with a loved one for a romantic cruise or enjoy the evening with a group of friends and experience the twinkling lights of downtown Boston. Cruise by the North End and catch a glimpse of the Old North Church made famous by the midnight ride of Paul Revere. Enjoy the buildings of downtown Boston such as the Custom House Tower, International Place, Independence Wharf and the New England Aquarium. Pass by the U.S.S. Constitution and hear how she got the nickname "Ironsides." View the Bunker Hill Monument, which sits behind the U.S.S Constitution. Marvel at the construction of the Leonard B. Zakim Bridge. Check out the colorful lights on the buildings in Boston’s Seaport District such as the new Vertex Building, World Trade Center and the Institute of Contemporary Art. The Northern Lights offers bench seating outside on the top deck as well as a climate controlled interior cabin. Adult beverages, soda, water and snacks are available for purchase by credit card only.


Other Sightseeing Options in Boston Waterfront

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What people are saying about Boston Waterfront

Overall rating

4.7 / 5

based on 58 reviews

This was such an unexpected treasure of a discovery in Boston! Besides having unseasonably beautiful weather for an October day, the sailing itself was terrific. Sails raised, light breeze once we motored out of the harbor and very peaceful. The crew was friendly and did not over narrate - they let us enjoy the day and answered any questions if asked. Seating is comfortable and lots of room. You can move around, there is a bathroom on board if needed. Bring a little picnic, order a cocktail, sit back and relax. Great value for the price. HIGHLY RECOMMEND!!!

I’ve long seen pictures of the ships with big sails raised. Now I have had the experience of sailing on one! Loved feeling the wind in my hair and watching the wind fill the sails that carried us across the water!

Beautiful day on the water, crew was great! I'd recommend this to anyone visiting Boston

So relaxing and fun! The crew we’re awesome and made it such a memorable experience.

It was a very nice and relaxing cruise around the harbor.