Add dates

Boston Waterfront Activities for couples

Our most recommended Boston Waterfront Activities for couples

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.

2 activities found
Sort by:

Other Sightseeing Options in Boston Waterfront

Want to discover all there is to do in Boston Waterfront? Click here for a full list.

What people are saying about Boston Waterfront

Overall rating

4.7 / 5

based on 96 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!

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.

Very relaxing. The captain and crew were fantastic!