Tours/Boston/Sightseeing Day Sail around Boston Harbor
Viator · group up to 80 pax

Sightseeing Day Sail around Boston Harbor

4.8(617)Boston1 hour
VIATOR4.8(401)TRIPADVISOR4.8(216)

Description

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of the sailboats from the 1890s. Sail past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island with Long Island Head Light. Great for families and friends who want to sail and see the sights of Boston from the water! Within minutes of leaving the dock, guests will forget the distractions of life on land and experience the joy of a leisurely sail. Sit back and relax as the crew raises sail and provides beverage service. Drinks are available for purchase by credit card only. Guests are welcome to bring a picnic onboard. The knowledgeable captain and crew are always ready to answer questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer.

Tour Options

2-hr Off Peak Day Sail
  • Aboard Adirondack II or III
1.5-hr Peak Day Sail
  • Aboard Adirondack II or III: Peak rates apply.
Oyster Sail Option
  • Must be 21+ to attend: Select this option to sail aboard one of our Adirondack Schooners with Oysters included. Duration: 2 hours Oysters : Enjoy a curated selection of local oysters, shucked on board and paired with mignonette, lemon, and hot sauce. Drinks available for purchase : Drinks are not included but available for purchase onboard.
1.5-hr Off Peak Day Sail
  • Aboard Adirondack II or III
2-hr Peak Day Sail
  • Duration: 2 hours Aboard Adirondack II or III

Itinerary

Pass by

Sail around Boston's Seaport District and take in 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 Castle Island featuring Fort Independence and the Donald McKay Monument, Spectacle Island, and Long Island with the Long Island Head Light House.

Highlights

This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks
Duration: Choose between a 1.5 or 2 hour sailing experience

What's included

Included
This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks
Duration: Choose between a 1.5 or 2 hour sailing experience
Not included
Beverages are not included, but are available for purchase by credit card only.
Gratuities (recommended for the captain and crew)
Food (guests are welcome to bring their own snack aboard)

Traveller Ratings

4.8
617 reviews
5
542
4
38
3
24
2
7
1
6

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 experience will be aboard Schooner Adirondack III or Schooner Adirondack IV
  • Large group bookings are not permitted. Multiple bookings are subject to added fees or cancellation by operator

Reviews(617)

J
jksager22
August 19, 2026
Sailing in Boston

Fantastic sailing experience. The crew were all very helpful and friendly. I will definitely take this trip again on my next visit to Boston.

M
Maps67535440094
August 17, 2026
Sail day

Relaxing 1.5 hrs on the water.

V
valeriesV6915IW
August 17, 2026
Great sailing

The weather was great. I wished they had pointed out more items all around us.

B
BarbieGS
August 16, 2026
Great sail in Boston Harbor

The crew was amazing! Andrew, Charlie and Mike were very friendly and made our trip fun and relaxing. they told us so many interesting facts about the harbor and the city of Boston. Don't miss this experience!

D
Dean_L
August 16, 2026
Great family activity

The crew was very helpful and knowledgeable. They do sell beverages on the ship but you are able to bring your own onto the ship too.

J
Julia_L
August 16, 2026
Sailing the Harbor!

It was great being on the water and seeing Boston Harbor in a unique way. The Captain and crew were very informative and personable.

P
Philip_R
August 14, 2026
Beautiful serene couple...

Beautiful serene couple of hours boating in the Harbor on a beautiful boat, the Adirondack II. Captain Eric and crew were great.!! Highly recommend.

J
Jennifer_O
August 13, 2026
Great cruise! Very chill...

Great cruise! Very chill and relaxing. Crew was super friendly. Highly recommend. Suitable for all ages.

L
Lukasz_S
August 13, 2026
Wonderful time spent...

Wonderful time spent sailing, totally relaxing and totally fun. One of the best things we did in Boston.

M
martinbM6748HP
August 11, 2026
“Come Sail Away!”

Our sightseeing day sail around Boston Harbor was amazing! We had great views of the skyline, Bunker Hill, Old Ironsides, Logan Airport and the Harbor Islands! It was pretty cool having the incoming flight path of airliners fly right over the sail boat as they approached the runway for landing! The best part of the entire cruise was the crew! From the Captain, Eric, to the 3 deckhands, Kira, Joe and John. They were very attentive and informative on everything from safety to sail handling and docking! Eric also had good anecdotes of Harbor sailing, given his experience on the water. I also found that the deck hand crew had a very varied and diverse background experience in work, study and travel. Also, it was great to be able to take the helm for a bit, under the watchful eye and guidance of the Captain. Everyone enjoyed that. The other passengers were fun to converse with and share the experience with! I would highly recommend this be a part of your Boston itinerary! You can’t go wrong with a great sunny afternoon, enjoying cocktails in Boston Harbor with great folks! Thank you! We’ll be back! “Party Marty”

Operator response

Martin, 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 your sightseeing day sail around Boston Harbor was such a memorable experience! It's wonderful to know you were well taken care of by the crew — Captain Eric, Kira, Joe, and John are truly a fantastic team. We look forward to your next visit! - Classic Harbor Line Boston

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