Savor evening skyline views with light commentary and music aboard a classic 1920s-style yacht.
2 hours
2-hour cruise, Light commentary
Glide through Boston Harbor at sunset aboard the classic yacht Northern Lights. Take in glowing skyline views while enjoying light commentary, music, and optional drinks.
Relax with friends as the city lights emerge and the USS Constitution signals dusk with its evening cannon.
Credit cards are the only form of payment accepted on board, and outside alcoholic beverages or coolers are not permitted.
No refunds are offered. You may reschedule or convert your booking to a gift card up to 24 hours before departure. If the operator cancels due to severe or unsafe weather, you can reschedule or receive a refund.
60 Rowes Wharf, Boston, MA 02110, United States
Classic Harbor Line's sunset sails consistently rank as travelers' favorite Boston activity, and it's easy to see why. The crew earns particular praise for being genuinely passionate about what they do—they're friendly, knowledgeable, and happy to chat about sailing or point out landmarks without overdoing the commentary. Guests appreciate that the boats feel spacious even with around 50 people aboard, and the two-hour duration hits the sweet spot between relaxing and keeping things interesting. The boarding process is straightforward, and reasonably priced drinks ($7) are available onboard. The route itself delivers some unexpected highlights. Sailing under planes landing at the airport gets mentioned repeatedly as a memorable moment, and watching the sunset over the city skyline before returning under the twinkling lights creates a perfect evening arc. The crew—captains, deckhands, and staff alike—clearly love their work and excel at making guests feel welcome without being intrusive. Multiple visitors who tried various Boston tours found this cruise to be their standout experience, which says something about the quality and atmosphere the team creates.
We took a sunset sailing cruise with Classic Harbor Line Boston on August 26, and are so glad we selected them! Amazing experience! The crew was super friendly and attentive, and you aren't on a large ship crammed full of people. Another bonus: The Classic Harbor Line sunset sailing cruise lasts 1/2 hour longer than the one provided by the other "popular" cruise line in the area. We watched the other sunset cruises heading into port while we continued to relax and enjoy the pleasant evening and beautiful city lights from the harbor. I'd venture to say this cruise was the highlight of our Boston trip. Highly recommend!!!!!!
Rom N.
September 8, 2025
We took a sunset sailing cruise with Classic Harbor Line Boston on August 26, and are so glad we selected them! Amazing experience! The crew was super friendly and attentive, and you aren't on a large ship crammed full of people. Another bonus: The Classic Harbor Line sunset sailing cruise lasts 1/2 hour longer than the one provided by the other "popular" cruise line in the area. We watched the other sunset cruises heading into port while we continued to relax and enjoy the pleasant evening and beautiful city lights from the harbor. I'd venture to say this cruise was the highlight of our Boston trip. Highly recommend!!!!!!
Rom N.
September 8, 2025