Tours/Boston/Boston Harbor Sunset Sail Tour
Viator · group up to 80 pax

Boston Harbor Sunset Sail Tour

4.8(155)Boston1 hour
VIATOR4.8(119)TRIPADVISOR4.8(36)

Description

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adirondack IV. Both sailboats are classically styled schooners and offer a smooth and gentle sailing experience as well as top-notch customer service by our captain and crew. Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the ambiance of a sunset sailing cruise aboard a beautiful sailboat.

Tour Options

Peak Sunset Sail
  • Aboard Adirondack II or III Peak Rates Apply
Peak Season Saturdays
Standard Sunset Sail
  • Aboard Adirondack II or III

Itinerary

Admission included120 min

Sail around Boston's Seaport District and Harbor for 2 hours as you take in the sunset views of many newly constructed buildings along with some classic structures that originally comprised Boston's waterfront community.

Pass by

Sail by Fan Pier and see the spanning Moakley Federal Courthouse, the World Trade Center and Harpoon Brewery.

Pass by

Sail amongst the Inner Harbor Islands of Boston Harbor including Spectacle Island and Long Island with the Long Island Head Light House.

Pass by

Sail by Castle Island, featuring Fort Independence and the Donald McKay Monument

Highlights

This is a 2 hour sailing experience in Boston Harbor.
This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks

What's included

Included
This is a 2 hour sailing experience in Boston Harbor.
This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks
Not included
Beverages are not included, but are available for purchase by credit card
Gratuities (recommended for the captain and crew)

Traveller Ratings

4.8
155 reviews
5
143
4
3
3
2
2
3
1
4

Important Information

  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Children must be accompanied by an adult
  • Minimum drinking age is 21 years. Coolers and outside alcoholic beverages are not permitted
  • Dress for the weather - it's often cooler on the water
  • Please let us know in advance if assistance is required for boarding
  • Only animals that perform a manual task to assist a person are permitted aboard. Emotional support animals and pets are not permitted
  • Plan to arrive at the ticket booth 15-30 minutes prior to the departure time. The meeting point is located directly behind the Boston Harbor Hotel in the Ferry Terminal just steps away from the dock. Boarding begins 5 minutes prior to the scheduled departure time.
  • This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks as we sail
  • This experience will take place on Schooner Adirondack II or III
  • The official route of this experience will depend on the wind
  • Large group bookings are not permitted. Multiple bookings are subject to added fees or cancellation by operator

Reviews(155)

C
clairemackenzie
July 3, 2026
A special way to spend the evening

From the moment we stepped aboard, everything about this sunset cruise was fantastic. The staff were genuinely warm, friendly and attentive, making everyone feel welcome throughout the evening. The boat itself was beautiful, impeccably maintained, comfortable and the perfect setting to watch the sun go down over Boston Harbor. The views were absolutely stunning, with the city skyline looking even more spectacular as the light changed. It was such a relaxing and memorable experience, and a real highlight of our time in Boston. I wouldn’t hesitate to recommend this cruise to anyone visiting the city. Thank you to the wonderful crew for making it such a special evening!

F
fitbaboss
June 29, 2026
Great sunset sail, 20 or so folks, no loud music, relaxing

This was a nice relaxing sail on the bay. No loud music and not a party boat. Be sure to bundle up or have layers as it might get cold. The sailing was great, the Captain zig zagged the boat so either side enjoyed the views, and yes they used the sails. Limited cocktails are offrered for a hefty price. Overall this is nice for a couple to enjoy.

E
Erick C
June 29, 2026
Beautiful Sunset Cruise

We had a wonderful sunset cruise of the harbor. The view from the ship of the sun setting over the Boston skyline was beautiful. The ship was very nice and clean and the staff were wonderful. Captain Dante and the crew were great at explaining the landmarks and answering questions about the ship and Boston in general. We had a great time.

Operator response

Erick, thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are delighted to hear that you enjoyed the stunning sunset over the Boston skyline. It's wonderful to know that Captain Dante and the friendly crew made your experience memorable by sharing their knowledge of the landmarks. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston

E
ERICK_C
June 29, 2026
Wonderful Sunset Cruise

We had such a nice time. The sunset over the Boston skyline was beautiful and the staff and ship are very nice. Captain Dante was great as well as the staff, Charlie and others were excellent at pointing out landmarks, explaining the ship workings and generally giving pointers on visiting the city. It was a great time!

M
Michelle_M
June 27, 2026
Loved it!!

Absolutely amazing. Michael and his crew were fantastic. The cruise was beautiful and we completely enjoyed it. Highly recommend!!

D
Denise_F
June 26, 2026
Very Dissapointex

We should have been notified that the cruise was cancelled. I’d like to have my account be credited so that I can use the unused monies fr an activity in my home town of Lex, KY. Thanking you in advance. I’ve been a loyal customer for many years.

Operator response

Denise, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are sorry to hear that you did not receive our notifications that your sail was canceled due to weather. We did call, leave a voicemail, send a text, and send an email to let you know as soon as we could once the trip had been canceled. Your booking has been fully refunded. We hope you will reconsider this review since we tried all possible methods available to us to contact you, and the cancellation due to weather was beyond our control, so we're not sure how we would have provided better customer service on this occasion, given the circumstances. We also hope you will be able to join us on another occasion in better weather! - Classic Harbor Line Boston

S
Summer_D
June 24, 2026
Must Do

Beautiful boat, great and knowledgeable crew! Amazing sunset and views of the city. They gave us panchos when it started raining!

J
Jennifer_A
June 22, 2026
Lovely ship. Would love...

Lovely ship. Would love to hear more about the harbor and see more areas. Sailing was wonderful. More of a tour would be great.

A
Amy_M
June 22, 2026
Absolutely recommend

It was a lovely experience and the crew couldn't have been more wonderful! Definitely recommend this tour/boat/crew!

C
Chelsea_S
June 17, 2026
A Sunset Dream!

We had an amazing experience with Eric, Claire and Alex on the Adirondack II last night! Beautiful weather, sky and amazing views! We can’t wait to book again when we come back! Also the SunBoy spiked water that Claire recommended 10/10!

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