Set sail on a private boat in Boothbay Harbor and witness one of Maine’s most breathtaking sunsets. Enjoy a personalized cruise on the Schooner Eastwind, offering serene waters, stunning views, and wildlife encounters that leave a lasting impression.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most people, no special fitness required
Wildlife
History
Boothbay Harbor has been a vital fishing and shipping port since the 19th century, with rich maritime heritage.
Conservation
Boothbay Sailing emphasizes eco-friendly practices, including waste reduction and wildlife protection during trips.
Boothbay Sailing
Set sail on a private boat in Boothbay Harbor and witness one of Maine’s most breathtaking sunsets. Enjoy a personalized cruise on the Schooner Eastwind, offering serene waters, stunning views, and wildlife encounters that leave a lasting impression.
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 for changing weather
Sea breezes can be cool even on warm days, so bring layers to stay comfortable.
Bring your camera or smartphone
Capture the vibrant colors of the sunset and scenic views during your sail.
Arrive early to board smoothly
Check-in 15-20 minutes before your scheduled departure to ensure a relaxed start.
Respect wildlife and quiet zones
Maintain a peaceful environment by observing wildlife from a distance and minimizing noise.
Warm, layered clothing
Layered apparel helps manage varying temperatures and wind while on the water.
spring|summer|fall|winter
Sun protection (hat, sunscreen)
Protects you from sun exposure during longer daylight hours.
summer|spring
Binoculars
Great for wildlife viewing, especially seabirds and marine mammals.
Waterproof footwear
Keeps your feet dry on deck in wetter conditions.
winter|fall