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Castle Island

Castle Island: Our most recommended tours and activities

Boston: Downtown Harbor Sailing Cruise

1. 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: Harbor Champagne Sunset Sail from Rowes Wharf

2. 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.

Downtown Boston Harbor Weekend Cruise with Brunch

3. Downtown Boston Harbor Weekend Cruise with Brunch

Weekends are a time for relaxing and getting your days started the right way. Join a Mimosa and Bloody Mary Cruise aboard the elegant Northern Lights to jump start your relaxation mode. While aboard, choose from a variety of mimosas and bloody Mary's. Enjoy the gourmet brunch buffet and select a cozy seat aboard the Northern Lights as you cruise around Boston Harbor to capture panoramic views of Boston. This is the perfect event for groups looking to entertain guests from out of town. You can see the sites without giving up a relaxing weekend. Small bridal parties can be accommodated and next day wedding parties. The Brunch Cruise offers the perfect event for individuals or a group looking to celebrate and relax. Also, see historic sites along the harbor such as: the harbor islands (Castle Island, Deer Island, Spectacle Island, Long Island, Lovells Island, Georges Island) Independence Fort, Bunker Hill Monument, USS Cassin Young, USS Constitution, Old North Church, Boston’s Seaport District with historic Fishing Markets and Boston’s incredible skyline.  Brunch features a diverse buffet menu to suit all palettes: Assorted Pastries, Scones, and Croissants Freshly Sliced Fruit and Berries Yogurt Cranberry Granola Smoked Salmon, Cream Cheese, and Jalapeno Bagels Scrambled Eggs with Herbs and English Cheddar (vegetarian) Roasted Potato and Sweet Potato Hash (vegetarian) Nueske’s Bacon and Chicken Apple Sausage. Summer Salad Please contact us in advance to inform us of any food allergies. Please note we cannot accommodate all food allergies, but we will do our best if given advance notice.

Boston: Scenic Harbor Cruise (Dog-Friendly)

4. Boston: Scenic Harbor Cruise (Dog-Friendly)

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.

Available activities

Other Sightseeing Options in Castle Island

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What people are saying about Castle Island

Overall rating

4.8 / 5

based on 274 reviews

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!

Amazing! We had such a good time. The Brunch was good, there was live music, the mimosas were great (that was an additional cost, but worth it). Weather and views were perfect. Very nice way to see Boston.

A wonderful experience, great crew, perfect weather. The guys made sure that everyone was taken care of and even took pictures if you so desired. Highly recommend

The crew was very engaging and attentive. Although it was a little nippy on the water, they offered fleece blankets that were perfect to take the chill off.

It was such a good time. Good was good, drinks was Amazing & bartenders was awesome