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Tours/Boston/Boston Harbor Sunset Sail Tour

Boston Harbor Sunset Sail Tour

4.8(186)Boston1 hour
VIATOR4.8(137)TRIPADVISOR4.8(49)
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
+9 photos
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour
Boston Harbor Sunset Sail Tour

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 Season Saturdays
Peak Sunset Sail
  • Aboard Adirondack II or III Peak Rates Apply
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
186 reviews
5
173
4
4
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(186)

J
Joyce_W
September 8, 2026
Excellent Experience

The Captain and crew were excellent. Very accommodating and knowledgeable of all questions that were asked.

K
Katrina_R
September 7, 2026
A Must Do!!

Sailing for the first time. I'm glad it was this company! Professional, and friendly! Thank you for best time amd experience!

C
Cheryl_M
September 2, 2026
What a great experience!

I booked this at the last minute and was so glad I did. The crew was great, kind and knowledgeable. The weather was perfect and the view from the boat was extraordinary at sunset. It was so nice to be with a small group of people rather than a large boat.

R
Rosa_M
September 1, 2026
Nice sunset cruise

Very organized and well planned sailing activity. All the crew was very attentive and nice. All my friends loved it

A
Amy_P
August 31, 2026
Add this to your list!

Beautiful weather and relaxing sailboat ride! Your view of the Boston skyline and the planes landing over the top of you at BOS is incredible!

P
Paige_F
August 30, 2026
Lovely activity!

This was such a. lovely sunset cruise in the harbor! Michael and his crew, Charlie and Kiara were very attentive and really seemed to love what they do. Highly recommend!

M
megantC3665KC
August 28, 2026
Boston Highlight

Absolute perfect sunset sail - crew was friendly and knowledgeable, made everything seem easy while still maintaining a strong sense of awareness and preparedness. The views were stunning and it was the Boston highlight of our family (of 7) trip.

Operator response

Megan, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are elated to hear that the sunset sail was such a highlight of your family's Boston trip! It's wonderful to know you were well taken care of by the friendly crew, and we hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston

B
burnsbee
August 26, 2026
Beautiful and Relaxing Sail

What a wonderful evening. Great views of the city. Fun experience with a great captain and crew. Very relaxing and enjoyable. We would do it again our next time to Boston. Couldn't recommend it more if you are looking for a fun beautiful way to spend an evening.

P
Pallavi_S
August 25, 2026
Great experience!

Must do if visiting Boston. One of the better ways to spend an evening on the water. I liked this better than the larger boats/ dinner cruises.

V
VALERIE_M
August 25, 2026
Evening cruise

Nice and Quiet, drinks were on your honor at 6.00 a piece!! My husband got to have the wheel for a while (we are sailers). Very clean boat would definately go again

$82/ person
4.8(186)
Duration1 hour
LanguagesEN
TicketMobile or paper ticket accepted
Travellers1–8 pax
ConfirmationInstant
OperatorClassic Harbor Line - Boston
Book on Viator →
Booking on the official Viator website
Free cancellation

For a full refund, cancel at least 24 hours before the scheduled departure time.

1+ days before100% refund
0–1 days before0% refund
Best price — we compare across partners
Secure booking on official partner site
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