Board a classic two‑mast schooner and watch Boothbay Harbor dissolve into islands, lighthouses, and working lobster boats as the sun sinks. This two‑hour sunset sail pairs easygoing windborne cruising with local stories about lobstering, seabirds, and coastal geology.
Board a classic two‑mast schooner and watch Boothbay Harbor dissolve into islands, lighthouses, and working lobster boats as the sun sinks. This two‑hour sunset sail pairs easygoing windborne cruising with local stories about lobstering, seabirds, and coastal geology.
The schooner slips from the dock as gulls wheel and the harbor exhales its last commuter boats. Salt air sharpens; masts creak into a steady rhythm. From the rail you watch the shoreline loosen into a series of rocky shoulders and small, wind-sculpted islands—lighthouses and lobster skiffs punctuating the horizon as the sun lowers.
Verified experiences and guided adventures in the surrounding area.
Operated by Boothbay Sailing · Boothbay Harbor, Maine
The schooner slips from the dock as gulls wheel and the harbor exhales its last commuter boats. Salt air sharpens; masts creak into a steady rhythm. From the rail you watch the shoreline loosen into a series of rocky shoulders and small, wind-sculpted islands—lighthouses and lobster skiffs punctuating the horizon as the sun lowers.
This stretch of midcoast Maine carries a straightforward maritime past: 19th-century shipbuilding yards, long seasons of lobstering and a living coastal culture that still runs on tide tables and weather notes. The bedrock here—granite and metamorphosed coastal formations—forces the water into channels and coves, producing the ebb and flow that define island access and safe anchorages.
On a two-hour sunset passage aboard a classic schooner you’ll trade the noise of land for wind and wake. Decks are open; views are uninterrupted except for masts. Expect narration from crew about local lobstering, the Burnt Island light, and seasonal seabirds. Harbor seals often flank the boat; in summer you might glimpse terns or offshore shearwaters drawn to baitfish.
Practicalities are simple: the cruise departs from Boothbay Harbor’s waterfront; arrive 15–20 minutes early, look for the "Schooner Eastwind" sign. BYOB snacks are allowed; there is a head on board. Dress in layers, bring windproof outerwear and motion-sickness remedies if you’re prone. The trip is suitable for most ages and mobility levels, but watch your step on wet decks. Plan to linger in town afterward—seafood shacks and galleries line the pier and make a full evening of the Maine coast.
The cruise is two hours and departs from the docks in central Boothbay Harbor—look for the 'Schooner Eastwind' sign.
Guests may BYOB drinks and snacks; the vessel has an onboard restroom but no full galley service.
Yes—infants must sit on an adult’s lap. The cruise is family‑friendly but supervise children on deck.
Trips are canceled for severe weather; full refunds are typically available if the operator cancels or you cancel at least 24 hours prior.
Boothbay Sailing operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.




The schooner slips from the dock as gulls wheel and the harbor exhales its last commuter boats. Salt air sharpens; masts creak into a steady rhythm. From the rail you watch the shoreline loosen into a series of rocky shoulders and small, wind-sculpted islands—lighthouses and lobster skiffs punctuating the horizon as the sun lowers.
The schooner slips from the dock as gulls wheel and the harbor exhales its last commuter boats. Salt air sharpens; masts creak into a steady rhythm. From the rail you watch the shoreline loosen into a series of rocky shoulders and small, wind-sculpted islands—lighthouses and lobster skiffs punctuating the horizon as the sun lowers.
This stretch of midcoast Maine carries a straightforward maritime past: 19th-century shipbuilding yards, long seasons of lobstering and a living coastal culture that still runs on tide tables and weather notes. The bedrock here—granite and metamorphosed coastal formations—forces the water into channels and coves, producing the ebb and flow that define island access and safe anchorages.
On a two-hour sunset passage aboard a classic schooner you’ll trade the noise of land for wind and wake. Decks are open; views are uninterrupted except for masts. Expect narration from crew about local lobstering, the Burnt Island light, and seasonal seabirds. Harbor seals often flank the boat; in summer you might glimpse terns or offshore shearwaters drawn to baitfish.
Practicalities are simple: the cruise departs from Boothbay Harbor’s waterfront; arrive 15–20 minutes early, look for the "Schooner Eastwind" sign. BYOB snacks are allowed; there is a head on board. Dress in layers, bring windproof outerwear and motion-sickness remedies if you’re prone. The trip is suitable for most ages and mobility levels, but watch your step on wet decks. Plan to linger in town afterward—seafood shacks and galleries line the pier and make a full evening of the Maine coast.