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 09 Jun

Other dates

You can choose the date already on the booking website

Starting at $66.54

Make a reservation

Mon 09 Jun

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)

Janine A

Sep 2018

I wanted to spend time on the water for my day off on Labor Day and the Adirondack III was perfect. It is a simple sail with hardworking crew eager to engage you in the experience or get you a drink. It is a no frills yet awesome way to spend a couple hours on the water. I will definitely do this one again and again.

kristencandersson

Aug 2018

I've taken the Adirondack III on three different occasions this summer - I would highly recommend it, it's a fabulous time to get out on the water and the crew is great!