Sail Boston Harbor on a Classic Schooner Day Cruise
Cruise Boston Harbor on a 1.5- or 2-hour schooner day sail
Duration
1.5 or 2 hours
Ideal For
Up to 54 people
Includes
1.5–2 hr sail, commentary
Highlights
Explore Boston Harbor on a 1.5- or 2-hour afternoon sail aboard the schooner Adirondack II or Adirondack III. Enjoy light commentary as you pass harbor landmarks and islands.
- Board an 80-foot pilot schooner modeled after the 1890s
- Spot the Boston Seaport District as you sail out
- See sites like the Moakley Federal Courthouse and World Trade Center
- Cruise past Inner Harbor Islands, including Castle Island and Spectacle Island
- Listen to light landmark commentary and ask the captain and crew questions
What's Included
- 1.5- or 2-hour sail
- Light commentary on landmarks
Things to know
No food is included; you may bring your own picnic. Drinks cost extra and can only be purchased with a credit card onboard, and gratuity is not included (groups of 12+ will be charged an additional 15% gratuity).
Cancellation Policy
You can reschedule or convert to a gift certificate up to 24 hours before departure. Refunds are not offered. If the operator cancels due to severe or unsafe weather, you can get a refund.
FAQs
Bring your own picnic if you’d like; no food is included. Do not bring outside alcohol or coolers. You can buy drinks onboard, but they cost extra.
Pay with a credit or debit card only. Cash is not accepted onboard.
Plan to pay extra for any drinks you purchase onboard. Gratuity is not included, and groups of 12 or more will be charged an additional 15% gratuity.
Meeting details
60 Rowes Wharf, Boston, MA 02110, United States
More about Castle Island
Castle Island sits at the southern edge of Boston Harbor, a historic peninsula crowned by the granite walls of Fort Independence and ringed by a breezy waterfront promenade that locals have treasured for generations. From the deck of the Adirondack schooner, Castle Island offers one of the most picturesque vantage points along the sail, its star-shaped fortress standing watch over the same waters that have welcomed ships for centuries. Sailing past Castle Island gives you a perspective few visitors ever get, viewing this beloved Boston landmark the way mariners have approached it since the 1600s.
As the schooner glides through Boston Harbor under billowing sails, Castle Island comes into view alongside other harbor highlights, with the salt air carrying the sound of gulls and the gentle creak of rigging overhead. You will feel the breeze fill the canvas as the city skyline frames the scene behind you and the fort's weathered stone walls catch the light. Unlike the busier downtown waterfront, the waters around Castle Island feel open and expansive, giving you space to settle into the rhythm of the sail with a drink in hand and the harbor stretching in every direction. Knowledgeable crew share stories of the harbor's seafaring history, and the slow pass near Castle Island is often a favorite moment for photographs.
This sail is perfect for couples seeking a romantic afternoon, friends celebrating a special occasion, or travelers who want to experience Boston from the water rather than the crowded streets. History lovers will appreciate the chance to see Castle Island and Fort Independence from a maritime angle, while anyone simply looking to unwind will find the unhurried pace of a classic schooner ideal for soaking in the views. Whether you are a first-time visitor curious about Boston Harbor or a longtime local who has only ever seen Castle Island from the shore, this day sail offers a fresh, memorable way to connect with one of the city's most cherished waterfront treasures.
