Schooner Eastwind Sunset Sail: Maine Coastline & Lighthouses

Lighthouses, fishing boats, and rocky islands from a deck with nothing between you and the horizon

A two-hour sailing tour aboard the Schooner Eastwind in Boothbay Harbor, Maine, where you watch the coastline unfold from a vessel designed to explore shallow waters and rocky coves. The boat uses an engine to reach the sailing grounds quickly, then relies on sail, and the open deck design means unobstructed views in every direction. Bring your own drinks and snacks; a restroom is on board.

Step-by-step itinerary

Two-hour schooner sailing tour

• Arrive at Boothbay Harbor docks
• Board the schooner Eastwind
• Sail to Maine coastline
• View lighthouses and wildlife
• Explore remote islands by boat
• Return to Boothbay Harbor docks

The Experience

The schooner leaves from Boothbay Harbor's historic waterfront, steps from shops and restaurants, and motors out to the sailing grounds in the time it takes to settle in. Once there, the sails go up and the engine cuts off—this is where the two-hour voyage actually begins. The boat's size and shallow draft let it reach areas bigger vessels cannot, so you see lighthouses up close, watch lobstermen working their traps, and pass islands that have no road access. The deck is clear except for the masts, which means you're not craning around railings or other passengers to see what's happening on the water.

The boat has been running this route for almost fifty years, and the crew knows which stretches of coast hold wildlife, where the light hits the islands at what hour, and what the working waterfront actually looks like when you're on it instead of looking at it from shore. The two-hour window is long enough to feel like a real voyage—not a quick loop—but short enough to fit into a day that includes the rest of Boothbay Harbor's waterfront. You bring your own non-alcoholic drinks and snacks, or you can purchase beer, wine and liquor on board.

What’s included

• Two-hour sailing voyage.
• unobstructed 360-degree views from every seat.
• onboard restroom.
• bring your own non-alcoholic drinks and snacks, or purchase beer, wine and liquor on board.

Good to know

Easy physical levelPublic transport nearbyInfants must sit on laps

Operated by Boothbay Sailing

Is this one for you?The commentary is delivered by crew who have worked this harbor for decades, so the tour works for anyone who wants to understand what they're seeing rather than just pass by it. Infants must sit on an adult's lap, and the boat suits all fitness levels, so families and mixed-ability groups fit comfortably.

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Top questions

What can I bring to drink on the Schooner Eastwind?

You're welcome to bring your own non-alcoholic drinks and snacks. The boat also sells beer, wine and liquor if you'd rather purchase on board.

How close do you get to the lighthouses?

The Schooner Eastwind's shallow draft and size let it explore areas larger boats cannot reach, so you see lighthouses much closer than you would from a bigger vessel or from shore. The exact distance depends on the day's conditions and which lighthouses are visible on your departure.

Is there a restroom on the boat?

Yes, there is a restroom on board during the two-hour sail.

What happens if the weather is bad?

Sailing conditions depend on wind and weather. Contact the operator directly about their policy for rough seas or storms; they can advise you on what to expect for your departure date.

Can I bring an infant on this tour?

Infants are welcome but must sit on an adult's lap during the sail.

Where exactly do we depart from?

The Schooner Eastwind departs from the center of Boothbay Harbor's historic waterfront, where you'll find the docks steps away from local shops, restaurants and inns.