Set sail aboard the historic Schooner Apple Jack and experience the thrills of traditional Maine sailing. Glide past stunning coastlines, spot wildlife like porpoises and Bald Eagles, and learn the ropes from friendly crew—all in just two hours of pure maritime adventure.
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most people; no special fitness required
Wildlife
History
Boothbay Harbor has operated as a vital fishing port since the 1800s, shaping its maritime culture.
Conservation
Boothbay Sailing emphasizes eco-friendly practices, respecting local wildlife and marine environments during sailing trips.
Boothbay Sailing
Set sail aboard the historic Schooner Apple Jack and experience the thrills of traditional Maine sailing. Glide past stunning coastlines, spot wildlife like porpoises and Bald Eagles, and learn the ropes from friendly crew—all in just two hours of pure maritime adventure.
Boothbay Sailing operates out of Boothbay Harbor, Maine, offering scheduled two-hour schooner sails that showcase the Midcoast Maine coastline. The operation runs historic schooners including the Schooner Apple Jack and the Schooner Eastwind, hosting both daytime and sunset departures. Trips include the Schooner Apple Jack Day Sail and Schooner Apple Jack Sunset Sail, plus the Schooner Eastwind Day Sail and Schooner Eastwind Sunset Sail. Each voyage emphasizes hands-on sailing opportunities, coastal sightseeing, and wildlife viewing such as porpoises and Bald Eagles. Passengers can help hoist sails, steer, or simply relax on deck while cruising past lighthouses, islands, and active waterfront scenes. The Schooner Eastwind offerings note nearly fifty years of local experience, and the Apple Jack sails depart from a central dock in Boothbay Harbor for easy access to visitors. Crews are described in public trip information as experienced and focused on safety and storytelling about the area’s maritime history. Boothbay Sailing caters to a range of guests including families, couples, and small groups seeking a scenic New England sailing experience. Advance reservations are recommended for peak summer dates. The business presents each trip as a two-hour excursion, making the sails a concise addition to a Maine vacation itinerary. Boothbay Sailing’s public descriptions emphasize authentic schooner vessels, accessible harbor departures, and opportunities to view coastal landmarks and wildlife from the water.
Public materials note unobstructed views at sunset sails and easy boarding for guests arriving from downtown Boothbay Harbor, making trips suitable for visitors of varied mobility levels and families.
Trip Length
2 hours
Consistent two-hour excursions
Location
Boothbay Harbor, ME
Harbor-front departures
Experience
Nearly 50 years
Local coastal expertise
Schooners
Apple Jack & Eastwind
Historic vessels in service
Book a day sail or sunset cruise aboard the Schooner Apple Jack or Schooner Eastwind — limited departures from Boothbay Harbor, Maine.
Dress for the weather
Bring layers and waterproof gear to stay comfortable on the water, regardless of conditions.
Arrive early
Get to the dock at least 15 minutes before your scheduled departure to ensure a smooth boarding process.
Bring a camera
Capture Coastline views and wildlife encounters—you won't want to miss the photo opportunities.
Bring binoculars
Optional but helpful for spotting distant wildlife like eagles and porpoises during the sail.
Layers and waterproof clothing
To stay comfortable and dry no matter the weather conditions on the water.
spring|summer|fall|winter
Sunscreen
Protect your skin from sun exposure while out on the open sea.
summer
Hat and sunglasses
Additional sun protection to keep glare at bay during your trip.
summer
Binoculars
Enhance wildlife viewing during your sail—spot porpoises, eagles, and more.
spring|fall|winter