Sail the historic schooner Eastwind through Boothbay Harbor’s quiet waters during a sunset cruise that combines local lore, gentle sailing, and unbeatable coastal views. Discover what makes this intimate onboard experience a standout in Maine’s outdoor adventure scene.
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; minimal physical exertion required.
Wildlife
History
Boothbay Harbor has deep maritime roots dating back to the 18th century, with schooners once integral to coastal trade and fishing.
Conservation
Efforts focus on preserving coastal water quality and protecting marine habitats that support local wildlife and fisheries.
Boothbay Sailing
Sail the historic schooner Eastwind through Boothbay Harbor’s quiet waters during a sunset cruise that combines local lore, gentle sailing, and unbeatable coastal views. Discover what makes this intimate onboard experience a standout in Maine’s outdoor adventure scene.
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.
Arrive Early for Boarding
Plan to arrive at least 15 minutes before departure to settle in and meet the crew.
Wear Layered Clothing
Coastal winds can turn cool quickly, especially at sunset—bring a light jacket or sweatshirt.
Motion Sensitivity Preparation
If prone to seasickness, consider taking medication beforehand; the harbor usually offers smooth conditions.
Camera Ready
Bring a camera or smartphone to capture the vivid colors of the sunset over Boothbay’s islands.
Windbreaker Jacket
Blocks coastal breezes and keeps you comfortable during open-water sailing.
spring|summer|fall
Non-slip Shoes
Provides safe footing on a wooden deck, especially when wet.
Sunglasses
Protects eyes from glare reflecting off the water during bright daylight hours.
summer
Camera or Smartphone
Captures stunning sunset colors and wildlife encounters.