Boston Harbor Sunset Sail on Schooner Adirondack
Savor a 2-hour sunset cruise past Boston Harbor landmarks aboard an elegant 80-foot schooner
From$109/ personincl. taxes and fees
Search all experiences
Discover what we've curated for you
Savor a 2-hour sunset cruise past Boston Harbor landmarks aboard an elegant 80-foot schooner
Discover what we've curated for you
2 hours
2 hour sail, Light commentary
Set sail on a 2-hour Boston Harbor sunset cruise aboard the elegant 80-foot schooners Adirondack II and III. Take in skyline and island views as the crew shares light commentary and ensures a relaxed, smooth ride.
Only credit cards are accepted for onboard purchases. No outside adult beverages or coolers allowed; food is not included and you may bring a picnic. All passengers, including infants and toddlers, must have a ticket.
Reschedule or convert to gift credit up to 24 hours before departure. No refunds otherwise. If the operator cancels, you may reschedule, receive credit, 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.
I bought tickets for the valentines brunch on the odyssey and it was amazing. Food was included and it was good I would recommend this 10/10
Richard Ibanez
February 19, 2026
I bought tickets for the valentines brunch on the odyssey and it was amazing. Food was included and it was good I would recommend this 10/10
Richard Ibanez
February 19, 2026