Boothbay Harbor Sunset Sail: Help Hoist Sails

Take the wheel of a working schooner and watch the light change across the water

The Schooner Applejack is a two-hour sunset sail on Maine's oldest windjammer in Boothbay Harbor, where you help hoist sails, steer the vessel, and pass Burnt Island Light, Squirrel Island and Ram Island Light while watching for bald eagles, osprey, harbor seals and porpoise. A live guide leads the tour in English. Children from age 6 are welcome. Restroom on board. Bring your own non-alcoholic snacks and drinks, or purchase beer, wine and liquor.

Step-by-step itinerary

Sunset sail on Boothbay Harbor

• Board Schooner Applejack
• Help hoist sails
• Take a turn at the wheel
• Sail past Burnt Island Light
• View Squirrel Island and Ram Island Light
• Spot porpoise, osprey, eagles, seals
• Observe local boats and lobster catch
• Enjoy 360-degree coastline views

The experience

The Schooner Applejack sits in Boothbay Harbor ready to sail at sunset. You board a working vessel, not a tour boat: the crew invites you to help raise the sails or take a turn at the wheel as the ship heads out past the lighthouses and islands that mark the outer harbor. The deck wraps around, so every seat gives a view of the coastline and the water. Two hours means you catch the light change without a full-day commitment, and the timing catches the harbor at its quietest.

As you sail, keep watch for bald eagles, osprey, harbor seals and porpoise. You'll pass local boats hauling lobster, the working side of the Maine coast most visitors miss from shore. The crew points out the landmarks (Burnt Island Light, Squirrel Island, Ram Island Light), and the smaller islands scattered through the outer harbor. The oldest windjammer in Boothbay means the boat itself has history. The intimate size keeps the group small enough that you're not crowded on deck.

There's a restroom on board. Bring a light jacket or sweatshirt because Maine weather shifts fast, even in summer. You can bring your own non-alcoholic snacks and drinks, or buy beer, wine and liquor once aboard. Service animals are welcome. Children from age 6 can sail. Younger children must sit on an adult's lap and still need a ticket.

What’s included

• Restroom on board.
• BYOB non-alcoholic snacks and drinks, with beer, wine and liquor available for purchase.
• live guide in English.

Before you book

Days and timesNext departure: 28 May 2027

Book up to2h before

AgesAdult (13 and older) · Child (6 to 12 years) · Under 6: can't be booked

GroupUp to 14 · max 6 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 4 days ago

Good to know

Low physical effortPets welcomePublic transport nearbyInfants must sit on laps

Operated by Boothbay Sailing

Is this one for you?Book this if you're staying in Boothbay Harbor and want hands-on sailing (help hoist sails or steer) in a two-hour evening window that leaves time for daytime exploring.

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Top questions

Can children come?

Yes. Ticket types: Child (6 to 12 years). Children under 6 can't be included in the booking.

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.

Can I actually help sail the Schooner Applejack, or do I just watch?

You can help hoist the sails or take a turn at the wheel. The crew invites participation, so the level of hands-on involvement is up to you: some passengers steer, others help raise canvas, and some prefer to sit and watch. Either way, you're part of the working vessel, not a spectator.

What wildlife might I see on the sunset sail?

Bald eagles, osprey, harbor seals and porpoise are common sights in Boothbay Harbor. You'll also see lobster boats working the water, which gives you a glimpse of the local fishing that defines the Maine coast.

How long is the sail and what time does it leave?

The sail is two hours and departs at sunset, so the exact departure time shifts with the season. The timing means you catch the light changing across the water and the harbor settling down as the day ends.

Is Boothbay Harbor easy to reach if I don't have a car?

Public transportation options are available nearby, so you can reach the harbor without driving. The Schooner Applejack docks in the center of Boothbay Harbor, a walkable tourist area with galleries, studios and restaurants.

What should I bring or wear for the sail?

Bring a light jacket or sweatshirt because Maine weather can change by the minute, even on a calm evening. Wear shoes with good grip for the deck. You can bring your own non-alcoholic snacks and drinks, or purchase beer, wine and liquor once aboard. Smoking and vaping are not permitted on the docks or the ship.