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

Boston Harbor Sunset Sail Tour

4.8(171)Boston1 hour
VIATOR4.8(127)TRIPADVISOR4.8(44)

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

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
171 reviews
5
159
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(171)

S
stacyjS5763RC
August 19, 2026
Very nice, beautiful scenery

It’s was a beautiful sail. Our captain and crew was exceptional. The only complaint I have is that I didn’t not know to bring our own snacks to go with our drinks.

S
Stantheeman
August 14, 2026
Superb Sunset Sail

This is my 5th time sailing with this company. Eric and his crew were incredible. We had a serene sunset sail in a light breeze up to Dorchester Bay and back. Next time I am in Boston I will be back sailing on Adirondack III

A
Avani_S
August 14, 2026
Must do!

Truly a dreamy experience! The crew is so kind & accommodating. Celebrated my friend’s birthday and she LOVED it. Would recommend 10000%.

J
Jill_V
August 11, 2026
Nice

Beautiful sunset cruise out of Boston Harbor. This is not a guided tour nor narration, but the crew is open and available for questions. Drinks available for sale onboard. Crew was gracious, knowledge and friendly. If you want a good seat be in line early, I cant imagine there was a bad seat on board, but seating was filled. Consider bringing binoculars to get a good view. Loved Captain Eric and crew John, Kira and Joe. Cost $79.00 a person was well worth it.

A
Armando_Z
August 10, 2026
Boat Tour was an amazing...

Boat Tour was an amazing experience! 2 hrs is perfect. The weather was great and attention to detail was awesome

L
laurielouhoo
August 10, 2026
Smooth sailing!

We really enjoyed the ship, captain Eric and the very cordial crew! Beautiful sailing in the harbor to see in the day, sunset and then the evening lights! Wonderful! All in our party enjoyed it!

Operator response

Laurie, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear that you and your party enjoyed the experience, from the daytime harbor views to the sunset and evening lights. It's wonderful to know that Captain Eric and our friendly crew made the voyage memorable. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston

V
Voyager01180468271
August 8, 2026
Excellent!

Fantastic experience. The crew of three were wonderful; they were friendly, experienced, and handled all aspects with efficiency. They created a comfortable, confident environment & the weather was perfect; great from start to finish.

Operator response

Thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are ecstatic to hear that you had a fantastic experience from start to finish! It is wonderful to know you felt well taken care of by the crew, and that their friendliness and efficiency helped create such a comfortable and confident environment. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston

H
heidibB8653FB
August 6, 2026
Clear sailing

Captain Dante and crew had a beautiful evening for sailing. Just enough wind to be able to shut the motor off and sail! Plenty of room for all. The beautiful schooner was clean and comfortable. The crew were cheerful, friendly, and efficient in service and in engaging with those on board. If you enjoy sailing, this is the cruise for you. The price is appropriate for the 2 hour sail. We will go again on another perfect sailing day.

Operator response

Heidi, thank you for booking a sail with us and taking some time to provide your valuable feedback and recommendation. We are elated to hear that Captain Dante and the friendly crew made your evening so memorable, with ideal wind conditions for a true sailing experience. It's wonderful to know you felt well taken care of and enjoyed the style of the boat. We look forward to your next visit! - Classic Harbor Line Boston

V
V2731RZamandak
August 6, 2026
Get on the water and enjoy the views

Guides were great and the experience was really cool. Was lovely to be on the water.

Operator response

Amanda, thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are delighted to hear that our guides made a great impression and that you enjoyed your time on the water. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Boston

J
Jeannine37
August 5, 2026
Beautiful….and perfect

Talk about perfect weather and sunset! I only took about 100 pictures🤣Wonderful crew and forever memories😉

Operator response

Thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are elated to hear that you experienced such beautiful weather and a stunning sunset — and 100 pictures sounds just about right! We are also glad the crew made your time memorable. We hope to have another chance to welcome you aboard! - Classic Harbor Line Boston

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