Boothbay Harbor: 2-Hour Schooner Sail & Maine Coast

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Free cancellationTravelers' pick

1/5

Duration2h

GroupUp to 28

Mobile ticketAccepted

What happens when you sail past a working lobster boat in Boothbay Harbor?

You board at Boothbay Harbor's historic waterfront and sail for two hours past lighthouses, fishing boats, and remote islands only accessible by water. The schooner's small size and unobstructed deck give you 360-degree views from any seat, and the engine gets you to open water fast so the sails can go up. Bring your own drinks and snacks, use the onboard restroom, and step off the dock back into the village shops and restaurants within walking distance.

Step-by-step itinerary

Two-hour sailing tour in Boothbay Harbor

Arrive at Boothbay Harbor docks
Board schooner Eastwind
Sail to Maine coastline
View lighthouses and islands
Observe fishing lobstermen and wildlife
Enjoy 360-degree deck views
Return to harbor docks

The Experience

You're standing on the deck of the Schooner Eastwind, and the Maine coastline unfolds in every direction. The boat leaves the historic waterfront docks in the center of Boothbay Harbor — you could walk to restaurants and shops from where you board — and within minutes you're past the breakwater, where the engine cuts and the sails go up. The whole point is to get you to the sailing grounds fast so you have real time on the water, not motoring around looking for wind.

The vessel itself is built for this harbor. It's small enough to slip into the rocky coves where you see actual fishing lobstermen working their traps, lighthouses perched on islands you can only reach by boat, and seals hauling out on the ledges. There are no railings or obstructions cluttering the deck except the masts, so from wherever you sit — and you can move around — you get a full 360-degree view. You're not watching Maine through a window or squeezed into a crowded tour boat. The two-hour sail is long enough to feel like you've left, short enough that you're not exhausted by the time you step back onto the dock.

The Schooner Eastwind has been running this same route for almost fifty years, and it shows in the details. They know the harbor the way locals know their own street. The crew moves with the kind of ease that comes from doing this hundreds of times — not rushed, not performing, just competent. You bring your own snacks and drinks (non-alcoholic), there's a restroom on board, and the docks sit steps away from the rest of Boothbay Harbor's waterfront, so you can grab lunch or coffee before or after without having to drive anywhere.

What’s included

Your two-hour sail includes use of the Schooner Eastwind, an onboard restroom, and a crew that knows Boothbay Harbor's waters.
Bring your own non-alcoholic snacks and drinks.
You board and return at the historic waterfront docks in the center of town, within walking distance of local shops, restaurants, and inns.

Good to know

Easy physical levelPublic transport nearbyInfants must sit on laps

Operated by Boothbay Sailing

Is this one for you?Book this if you want to see the Maine coast from the water without arranging a private charter or spending half a day on a larger tour boat — two hours is enough to feel like you've sailed, short enough to fit into a day that includes exploring the village.