Boston Harbor Sail: Classic Schooner with Harbor Islands
Glide past historic islands aboard a classic 1890s schooner, savoring the sea breeze and views.
A 1.5 or 2-hour sail around Boston Harbor aboard Schooner Adirondack III or IV, classic wooden boats built in the style of 1890s sailing vessels. You sit on deck while the crew raises sail and the captain answers questions about the sights, landmarks and maritime history of Boston Harbor and its islands. Beverages are available for purchase. You're welcome to bring a picnic aboard. Arrive 15–30 minutes before departure at the Ferry Terminal behind the Boston Harbor Hotel.
Step-by-step itinerary
Sail around Boston Harbor sights
- Board schooner Adirondack sailboat
- Sail past Boston Seaport District
- View Fan Pier and landmarks
- Sail among Boston Harbor Islands
- See Castle Island and Fort Independence
- Pass Spectacle Island and Long Island
- Enjoy beverage service onboard
- Learn about Boston Harbor history
The experience
The difference between watching the harbor from a motorboat and sailing it is the difference between being towed and being carried. Within minutes of leaving the dock, the crew raises sail and the boat settles into the rhythm of the water. The captain and crew are there to answer questions about what you're seeing (the Seaport District's mix of new construction and original waterfront buildings, Fan Pier and the Moakley Federal Courthouse, the World Trade Center, Harpoon Brewery), but this isn't a narrated tour where someone is talking at you the whole time. You get to decide how much you want to listen and how much you want to sit back and let the sail do the work.
The route takes you past the Inner Harbor Islands: Castle Island with Fort Independence and the Donald McKay Monument, Spectacle Island, and Long Island with the Long Island Head Light. These are the sights that define Boston from the water, and seeing them from a wooden schooner (the kind of boat that would have worked these same waters over a century ago) changes how they land. You can bring a picnic aboard if you want to eat your own food, and drinks are available for purchase by credit card. The crew handles the sailing. You handle the pace of your own day on the water.
Choose between a 1.5-hour or 2-hour sail depending on how much time you have and when you want to go: peak and off-peak options are available. Plan to arrive at the ticket booth 15–30 minutes before departure. Boarding starts 5 minutes before the scheduled time. Dress for the water. It's often cooler out there than it looks from the dock. Service animals are allowed aboard. Emotional support animals and pets are not.
What’s included
- Your sail includes the crew raising and managing the canvas, the captain's knowledge of Boston Harbor sights and maritime history, and your choice of a 1.5 or 2-hour route.
- beverages are available for purchase by credit card, and you're welcome to bring your own picnic aboard.
Options for this experience
5 optionsSee 2 more options
Information
Lasts 1h 30m–2h, from US$ 54.44 per person, with a live guide in English and with free cancellation up to 24 h before.
Prices and times updated 4 days ago
Operated by Classic Harbor Line - Boston
Is this one for you?Pick the 2-hour sail if you want time to settle into the rhythm of the boat and take in the harbor without rushing. The 1.5-hour option works better if you're fitting the sail into a shorter window but still want to see the same islands and landmarks. Either way, you're getting the experience of sailing itself, not just being transported past the sights. That's what separates a schooner from a motorboat tour.
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Top questions
Can children come?
Yes. Ticket types: Child (3 to 14 years); Infant (under 3): free.
What happens if it rains?
It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.
What's the difference between the 1.5-hour and 2-hour Boston Harbor sails?
Both routes cover the same sights: the Seaport District, Castle Island, Spectacle Island, and Long Island with the lighthouse. The 2-hour sail gives you more time on the water and a longer experience of the sailing itself. The 1.5-hour sail covers the same ground in a shorter window. Both are available at peak and off-peak times.
Can I bring food and drinks aboard the Boston Harbor sail?
You're welcome to bring a picnic and eat it on deck. Beverages are available for purchase by credit card only. Coolers and outside alcoholic beverages are not permitted. The crew will serve drinks if you order them.
What is Fort Independence on Castle Island?
Fort Independence is a historic fortification on Castle Island, one of the Inner Harbor Islands you'll sail past. The captain can tell you more about its history and the Donald McKay Monument nearby as you pass.
Do I need sailing experience to go on this tour?
No experience is necessary. The crew handles all the sailing while you sit on deck and relax. The captain and crew answer questions about the sights and history, but you're not expected to do anything except enjoy the sail.
Where do I meet the boat for the Boston Harbor sail?
The meeting point is at the Ferry Terminal directly behind the Boston Harbor Hotel, just steps from the dock. Arrive 15–30 minutes before your scheduled departure time so you can check in at the ticket booth.
Boston Harbor Sail: Classic Schooner with Harbor Islands
1h 30m–2h · EN
from US$ 54.44 per person