Boothbay Harbor Schooner Sails
Boothbay Harbor's two schooners, Eastwind and Applejack: day and sunset sails past three lighthouses, times, prices, the no-BYO bar rule, parking and Pier Six.
Boothbay Harbor has two schooners, Eastwind and Applejack, both run by Boothbay Sailing from Pier Six on Commercial Street. Each sails for two hours, out past Burnt Island Light, Squirrel Island and Ram Island Light to the outer islands, with day sails and a sunset sail. The decks are open, with a view all round from every seat, and the crew uses the engine to reach the sailing grounds quickly. Both boats carry a licensed bar, so you cannot bring your own alcohol, though food and soft drinks are welcome. Eastwind takes children of any age; Applejack is not for children under five or anyone with limited mobility.
Day sail or sunset, Eastwind or Applejack
| Sail | Times on the operator’s site | Ages | Listing price |
|---|---|---|---|
| Eastwind day sail | 10:00 am, 12:30 pm, 3:00 pm | All ages; under 3 free | From $60 |
| Applejack day sail | 9:00 am, 11:30 am, 2:00 pm | 5 and over | From $65 |
| Eastwind sunset sail | Varies with the sunset | All ages | From $75 |
| Applejack sunset sail | Varies with the sunset | 5 and over | From $75 |
Times and age rules from Boothbay Sailing’s own website, which prints no year; listing prices checked October 2026.
Boothbay Sailing’s own prices are $54.95 for ages 13 and over on either day sail and $59.95 on the sunset sails, with $39.95 for children (checked October 2026). A booking on the GetYourGuide listings can be cancelled for a full refund up to 24 hours before; a booking made with Boothbay Sailing directly is forfeited inside 48 hours unless you buy its Trip Protection.
The 2027 calendars open on 28 May for both schooners and run to 11 October for Eastwind; Applejack’s day sails go on to 24 October (read October 2026). On the 2027 calendar Applejack’s day sails leave at 11:30 am and 2:00 pm, so go by the time on your booking.
The route
Both schooners set the same course: out of the inner harbor past Burnt Island Light, by Squirrel Island, out to Ram Island Light and the outer islands of Boothbay. On the way you pass lobster boats setting and hauling their traps, and the crew watches for porpoises, ospreys, bald eagles and harbor seals. Guests can help hoist the sails or take a turn at the wheel.
Checking in and boarding
- Where: Pier Six, 20 Commercial Street. Check in at the Eastwind ticket booth in the Fisherman’s Wharf Inn parking lot, 30 minutes before; for Applejack the staff walk you to her berth.
- Boarding: the crew opens the gate 15 minutes before departure.
- On board: each schooner has a head below deck, down a ladder.
- Wear: a couple of layers and a windbreaker. Even on a hot day in town, the sea off Boothbay cools the air.
Parking
You cannot park at the Fisherman’s Wharf Inn. The town runs four municipal lots, Footbridge (66 spaces), Howard Street (79) and Oak Street (27), plus six meters on Howard Street, at $2.00 an hour, seven days a week from June 1 to Columbus Day.
Boarding and parking from Boothbay Sailing’s own website, checked October 2026.
Windjammer Days
Boothbay Harbor’s own windjammer festival, Windjammer Days, runs from Sunday June 27 to Saturday July 3, 2027, its 65th year, with a parade of sail into the harbor. The Camden Windjammer Festival guide covers it with the other schooner events of the season.
Who should pick something else
- Bring your own wine: Surprise in Camden and Portland Schooner Co. both allow it; see Camden and Portland.
- A child under five, or limited mobility: take Eastwind rather than Applejack.
- Sail at sunset: the sunset sails guide puts the evening departures beside the sunset times.
- The season: the schooner season guide has every harbor month by month.
Sail out of Boothbay Harbor on Eastwind
Two hours on Eastwind's open deck from Pier Six, past lighthouses, islands and the lobster boats at work.
See 2027 dates