Sightseeing Day Sail around Boston Harbor

Overview

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.

City: Boston

Mon 02 Feb

Other dates

You can choose the date already on the booking website

Starting at $66.54

Make a reservation

Mon 02 Feb

Starting at $66.54

Make a reservation

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What's 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

Additional Info

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

What To Expect

Classic Harbor Line Boston MA Day Tours

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

Fan Pier

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

Boston Harbor Islands State Park

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.

Cancellation Policy

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

Traveler Photos

Reviews (380)

David D

Jul 2019

The weather was not great on our said day, but there was a break and the crew was able to bring the group out. Captain Eric and crew members Madeline and Teres made us feel welcome and safe. We packed some sandwiches and snacks and purchased some beverages on board. The schooner Adirondack III was a nice way to spend an hour or two. Despite the clouds and rain, we had nice views of the harbor, castle island and enjoyed watching the planes land right over our heads. I would recommend this trip.

Sacredspaces

Jul 2019

I took my sister visiting from OR out on this cruise. The wind was a bit high but nothing I was aware of while on land. yet when we went out on the water...what a blast!! It was by far one of the best sailing adventures I have been on. Not a lot of blaring commentary over a loud speaker, just the beautiful views and experience of the harbor. The staff was attentive and will discuss the sights if you want to engage them. I will be going back!!

KristinTodd86

Jun 2019

This was the PERFECT way to celebrate my bday! A 2 hour sail on board the Adirondack III was a dream. Beautiful views of the skyline, the harbor, the islands. The crew - Shaun (aka Julian Edelman), Madeline & Amelia made the experience A+ right down to the smallest of details. So friendly, fun & knowledgable. Blankets if it’s chilly. Even had the passengers sing to me. Next time we’ll bring a better spread to share. Tx again!! We’ll be back soon!