Set sail on a captivating 2-hour journey aboard the Schooner Lazy Jack in Boothbay Harbor. Experience stunning coastal views, wildlife encounters, and a memorable sunset over Maine’s rugged shoreline. Read on to find out why this sailing adventure is a Maine favorite.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; no physical exertion required beyond sitting and enjoying the scenery.
Wildlife
History
Boothbay Harbor has been a major hub for Maine’s fishing and shipping industries since the 19th century, with vessels like the Schooner Lazy Jack echoing maritime traditions.
Conservation
Boothbay Sailing emphasizes low-impact tourism, promoting responsible wildlife viewing and preserving the region's natural beauty for future generations.
Boothbay Sailing
Set sail on a captivating 2-hour journey aboard the Schooner Lazy Jack in Boothbay Harbor. Experience stunning coastal views, wildlife encounters, and a memorable sunset over Maine’s rugged shoreline. Read on to find out why this sailing adventure is a Maine favorite.
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 in layers
The weather on the water can change quickly; bring layered clothing to stay comfortable.
Bring binoculars
Enhance wildlife viewing, especially for spotting eagles and porpoises.
Arrive early
Getting to the dock 15-20 minutes before departure ensures smooth boarding.
Bring sun protection
Evening cruises can still be sunny; pack sunscreen and hats.
Windbreaker or light jacket
Provides comfort against the sea breeze, especially at sunset.
spring|summer|fall|winter
Sunscreen
Protects your skin during daylight hours on the water.
summer
Binoculars
Helps spot wildlife like eagles and porpoises at a distance.
Hat with brim
Provides sun protection during the cruise.
summer