Boothbay Harbor: Schooner Day Sail & Maine Coastline Views

Summary

Schooner sailing in Boothbay Harbor with lighthouses, local boats and wild islands

You’ll step aboard a classic Boothbay Harbor schooner for a two-hour sail along Maine’s rugged coastline—passing lighthouses, waving at lobstermen, spotting seabirds and wild islands only boats can reach. Bring your own snacks or drinks (non-alcoholic) and settle into any spot on deck for 360-degree views, fresh air, and that rare kind of quiet you can only find under full sail.

What’s the experience like?

“You ever tried to say ‘Eastwind’ with a mouthful of salt air?” That’s what our captain joked as we pulled away from the dock in Boothbay Harbor. I could still smell coffee from the bakery across the street mixing with the seaweed and boat varnish. There were maybe a dozen of us—some couples, a family with a little girl who kept pointing at every seagull like it was her first time seeing one (maybe it was). The schooner itself felt solid underfoot, all smooth wood and ropes that creaked when the wind picked up. I liked that you could just sit anywhere—no bad seats, really.

We motored out past lobster boats—one guy waved, cigarette dangling from his mouth—and then the sails went up. It got quiet in this way you only get on water, just canvas snapping overhead and the occasional gull. Our guide (I think his name was Tom? Or maybe Tim—I’m terrible with names) pointed out Burnt Island Light off to starboard. He told us how some of those islands are only reachable by boat; apparently, people still live out there year-round. Hard to imagine in January. The sun kept shifting behind clouds and back again—Maine weather is moody like that.

I brought my own lemonade (they said BYOB but no booze), which tasted weirdly better out there than it ever does at home. Someone else had packed sandwiches—good idea for next time. There’s a restroom below deck if you need it, though I never did; too busy watching cormorants dive near the rocks or just zoning out at all that blue-gray water. The whole thing lasted about two hours but felt longer—in a good way. I still think about that silence after they cut the engine, just wind and water and nothing else for a while.

Step-by-step itinerary

Day 1 — Two-hour sailing tour in Boothbay Harbor

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

Top questions

How long is the Boothbay Harbor schooner day sail?

The day sail lasts approximately two hours from departure to return.

Are snacks or drinks provided on board?

No food or drinks are provided, but you can bring your own non-alcoholic beverages and snacks.

Is there a restroom available during the cruise?

Yes, there is a restroom available onboard for passenger use during the tour.

Where does the schooner depart from in Boothbay Harbor?

The docks are located in the center of Boothbay Harbor's historic waterfront area.

Is this sailing trip suitable for children or infants?

Yes, children are welcome; infants must sit on an adult’s lap during the tour.

Can I access public transportation to reach the dock?

Yes, public transportation options are available nearby Boothbay Harbor's waterfront.

What’s included

Your sailing trip includes two hours aboard a classic schooner departing from central Boothbay Harbor, with 360-degree open-deck views of Maine’s coastlines and islands. There’s an onboard restroom for comfort throughout your journey, plus you’re free to bring your own non-alcoholic drinks or snacks to enjoy as you watch lobstermen work or spot wildlife along the way.