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Castle Island

Castle Island: Our most recommended tours and activities

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

1. Boston: Harbor Champagne Sunset Sail from Rowes Wharf

Embark on a sightseeing sunset cruise on Boston harbor and soak up the views of the famous skyline. Admire city highlights, including the Inner Harbor Islands and the Boston Fish Pier.    Board an elegant sailing yacht, the ' Adirondack III.' Travel in style on a classic 80 foot pilot schooner that is comfortable and spacious. Glide smoothly over the water and have the option of purchasing a refreshing drink at the onboard bar. Admire views of the historic scenery of Boston Harbor as you pass by the Boston Fish Pier and the Moakley Federal Courthouse at Fan Pier. Capture pictures of Castle Island and the Donald McKay monument. Cruise through the Inner Harbor Islands. Step back in time as you cruise by the historic Charleston Navy Yard. Go by the lush greenery of the Waterfront Park and take in the modern architecture of buildings like the New England Aquarium. Take a selfie in front of the Boston skyline. Have your questions about the sights and history of Boston Harbor and its surrounding areas answered by the attentive crew. Hear facinating facts and old-time legends about the maritime world of Boston. Return to your meeting point at the end of the tour.

Boston: Downtown Harbor Sailing Cruise

2. Boston: Downtown Harbor Sailing Cruise

Experience Boston like never before onboard the 80-foot pilot schooner Adirondack III. Enjoy a round-trip of 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 onboard, while complimentary soda and water will keep you hydrated along the way.

Boston: 1.5-Hour Dog-Friendly Harbor Cruise

3. Boston: 1.5-Hour Dog-Friendly Harbor Cruise

Enjoy a relaxing sightseeing cruise with the entire family — dogs included. As you sail along the Boston Harbor, see beautiful views of the skyline and tick off the city highlights. Start from Rowes Wharff and glide past such historic landmarks like the Federal Courthouse, the Seaport District, and the working pier. Enjoy snacks and drinks available on board as you take photos of the Boston skyline. See the historic USS Constitution, the US Navy's oldest warship, in her berth in the Charleston Navy Yard. Finish the cruise at the North End of the harbor and head back to Rowes Wharf.

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Other Sightseeing Options in Castle Island

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What people are saying about Castle Island

Overall rating

4.8 / 5

based on 232 reviews

It was a great experience with a great crew. The weather was amazing and actually sailing was great. They had beverage options for purchase (though I did think I was doing a champagne cruise). I’d definitely go again.

The wharf area was impressive. It was a great evening for sailing and the views were amazing. We enjoyed talking with the captain and the crew was professional and friendly. Fun times for sure, highly recommended!

Absolutely recommend! Friendly crew, beautiful sailing ship and amazing views of the city. Best thing to do in Boston!

This was a great evening sailing in the Boston Harbor with team members for a work outing! Highly recommend doing!

Very relaxing. The captain and crew were fantastic!