Boston Harbor Sunset Sail: 2-Hour Schooner Tour

Watch the sunset from the water while the city's landmarks slip past.

A 2-hour sailing tour of Boston Harbor aboard Schooner Adirondack II or III, departing at sunset and passing Castle Island, Fan Pier, the Harbor Islands and the Seaport District's mix of new and historic waterfront. The crew is available to answer questions about the sights, though this is not a narrated tour. Arrive 15–30 minutes before departure at the Ferry Terminal behind the Boston Harbor Hotel. Boarding opens 5 minutes prior. The actual route depends on wind conditions. Beverages are available for purchase. Gratuities for the captain and crew are recommended.

Step-by-step itinerary

Sunset sailing around Boston Harbor

• Board schooner Adirondack III or IV
• Sail around Boston's Seaport District
• View Fan Pier and Moakley Courthouse
• Pass by World Trade Center and Harpoon Brewery
• Sail among Inner Harbor Islands
• See Long Island Head Light House
• Pass Castle Island and Fort Independence
• Enjoy sunset views over Boston Harbor

The experience

The boat leaves the dock directly behind the Boston Harbor Hotel, and within minutes the city noise fades. You're on the water for 2 hours as the sun moves toward the horizon, and the route shifts with the wind: sometimes you'll sail past Fan Pier and the Moakley Federal Courthouse, sometimes deeper into the Inner Harbor Islands where Spectacle Island and Long Island come into view, or out toward Castle Island and Fort Independence. The crew knows the landmarks and will answer what you ask, but they're not narrating a script. The point is the sailing itself and the way the light hits the Seaport's new glass buildings alongside the older brick structures that made Boston's waterfront what it was.

Both schooners are classically styled and built for a smooth ride. Dress for the water (it's cooler out there than on the street), and plan to arrive at the ticket booth 15 to 30 minutes early. Service animals are welcome. Emotional support animals and pets are not. Children must have an adult with them. If you need help boarding, let the operator know in advance.

What’s included

• 2-hour sailing experience aboard Schooner Adirondack II or III.
• views of Castle Island, Fan Pier, the Seaport District and Boston Harbor Islands.
• crew available to answer questions about landmarks and sights.

Options for this experience

3 options

Standard Sunset SailGuide in English · Available from 1 May 2027Onboard the Adirondack II or III

Peak Sunset SailGuide in English · Available from 8 May 2027Onboard the Adirondack II or III; peak rates apply

Peak Season SaturdaysGuide in English · Available from 29 May 2027

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesNext departure: 1 May 2027

Book up to2h before

GroupUp to 80 · max 8 per booking

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Easy physical levelPets welcomePublic transport nearby

Operated by Classic Harbor Line - Boston

Is this one for you?Book the Peak Sunset Sail or Peak Season Saturdays option if you want to sail during the most vivid light. The Standard Sunset Sail departs earlier in the season when the sun sets later and the harbor is quieter. Either way, the route and timing shift with the wind, so no two sails are the same.

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Top questions

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 landmarks will I see on the Boston Harbor sunset sail?

The sail passes Castle Island with Fort Independence, Fan Pier and the Moakley Federal Courthouse, the World Trade Center, Harpoon Brewery, and the Inner Harbor Islands including Spectacle Island and Long Island with its lighthouse. The exact route depends on wind conditions that day.

How long is the Boston Harbor sunset sail?

The tour is 2 hours on the water. Plan to arrive 15–30 minutes before your scheduled departure time for boarding.

What's included in the sunset sail ticket?

The ticket covers the 2-hour sailing experience aboard the schooner and access to the crew's knowledge of the sights. Beverages are available for purchase by credit card during the sail. Gratuities for the captain and crew are recommended but separate.

Where do I meet the boat for the sunset sail?

The meeting point is at the Ferry Terminal directly behind the Boston Harbor Hotel, just steps from the dock. Boarding begins 5 minutes before the scheduled departure time.

Can I bring my pet or service animal on the sunset sail?

Service animals that perform a manual task to assist a person are permitted. Emotional support animals and pets are not allowed aboard.

What should I wear for the Boston Harbor sunset sail?

Dress for the weather and expect it to be cooler on the water than on land. Bring layers or a jacket even if the day feels warm ashore.