Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

If you’re looking for a memorable way to see Maine’s rugged coastline, a sailing cruise in Boothbay Harbor might just be the ticket. This 2-hour trip on the Schooner Apple Jack offers a taste of traditional Maine maritime life, blending scenic views, wildlife spotting, and a touch of nautical history. We’ve gathered insights from travelers who’ve enjoyed this outing to help you decide if it’s worth hauling your sunscreen and hat along.

What we love about this cruise is how it combines stunning vistas of lighthouse-lit coastlines with the chance to see porpoises, bald eagles, and harbor seals — all from the deck of Boothbay’s oldest windjammer. Plus, the crew’s warmth and knowledge help make the experience feel authentic and engaging. A potential consideration is that at just two hours, it’s a quick trip, so if you’re craving a full-day adventure, this might feel a bit light. It’s best suited for those who want a relaxed, scenic outing with plenty of opportunities for photos and wildlife encounters, especially families, first-time visitors, or anyone eager to experience Maine’s maritime charm.

Key Points

• Authentic Maine experience: Sail on Boothbay’s oldest windjammer, combining history with scenic beauty.
• Wildlife spotting: Look out for porpoises, bald eagles, and harbor seals, making it ideal for nature lovers.
• Expert crew: Friendly, knowledgeable guides enhance the trip with interesting stories and hands-on participation.
• Great value: At $55 per person for two hours, it’s an affordable way to enjoy Maine’s coast with plenty of memorable sights.
• Flexible booking: Cancel up to 24 hours in advance or reserve now, pay later, for travel flexibility.
• Refreshments: Alcohol is available for purchase onboard, but bring your own food and drinks if you prefer.

You can check availability for your dates here:

An In-Depth Look at the Schooner Apple Jack Experience

Setting Sail: The Itinerary and Atmosphere

From the moment you arrive at the Fisherman’s Wharf Inn parking lot, the vibe is inviting. A prominent Schooner Eastwind Boarding sign guides you to your departure point. As the crew hoists the sails, a sense of anticipation builds. The boat, being the oldest windjammer in Boothbay, offers a tangible connection to maritime history. The sails catch the breeze, and you feel the wind through your hair — this isn’t just a boat ride; it’s a slice of nautical Maine.

As the schooner glides away from the dock, you’ll be treated to expansive views of rugged coastlines, remote islands, and cozy coastal homes. These sights are unique to boat trips — you won’t see them from land, making it well worth the price. The scenery is punctuated by Burnt Island Light, Squirrel Island, and other outer islands, which appear as quiet outposts rather than tourist hotspots.

What Makes It Special?

Travelers note that the crew’s friendliness and knowledge stand out. Captain Josh and Christina, in particular, are praised for their engaging manner. One reviewer commented, “Josh and Christina made the trip relaxing and fun,” illustrating how the crew’s personality adds a layer of enjoyment beyond the scenery.

Another aspect that earns high marks is the opportunity for hands-on participation. Volunteers often help hoist sails or steer the schooner, making the experience more immersive and memorable. This isn’t a passive ride; it’s a chance to get a feel for traditional sailing, especially if you’ve ever wondered how sailors did it before GPS and motorboats.

Wildlife and Scenery: The Highlights

The real treat is spotting the abundant wildlife. The waters around Boothbay harbor are teeming with life, as confirmed by multiple reviews mentioning encounters with porpoises, harbor seals, and the regal sight of bald eagles overhead. The crew is attentive, pointing out these animals and sharing interesting facts, which adds educational value to the cruise.

The lighthouse views are breathtaking. Burnt Island Light is a classic Maine lighthouse, and sailing past it at close range provides fantastic photo opportunities. Some travelers wish the trip included a circumnavigation of smaller islands, but most appreciate the focus on the main sights.

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Onboard Comfort and Extras

The boat features restrooms onboard, which is a thoughtful touch on a 2-hour trip. For those interested in a drink, alcohol is available for purchase, including beer, wine, and cocktails like Bloody Marys — perfect for unwinding with the sea breeze. However, bringing your own food and non-alcoholic beverages is recommended if you want to snack or hydrate without additional costs.

Pricing and Value

At $55 per person, the cruise offers solid value. Compared to larger, more commercial tours, this sail provides an intimate experience with a focus on genuine scenery and wildlife. You get about two hours of sailing, which is enough time to relax, take photos, and enjoy the crew’s commentary without feeling rushed.

Group Size and Booking

Most trips have around ten passengers plus two crew members, creating a cozy atmosphere without feeling crowded. Flexible booking options, including free cancellation up to 24 hours before and the ability to reserve now and pay later, make planning easy, especially for those with unpredictable schedules.

Reviews Speak for Themselves

An impressive 36 reviews with a 4.9-star rating underscore the quality of this experience. Reviewers consistently praise the “friendly and knowledgeable” crew, the beautiful scenery, and the overall value. Families report that children and grandchildren thoroughly enjoy the trip, citing its relaxed, engaging atmosphere.

Why Choose This Cruise?

This sailing trip is ideal for travelers who want a laid-back, authentic maritime experience. It’s perfect for first-time visitors wanting a quick yet memorable glimpse of Maine’s coast, wildlife enthusiasts, or anyone eager to learn about local nautical history. The combination of scenic beauty, wildlife encounters, and friendly guides makes it a well-rounded activity.

However, if you’re seeking a longer, more extensive adventure or land-based activities, you might find this trip a little brief. But for a quick escape into the sea, it hits all the right notes.

The Sum Up

The Boothbay Harbor Schooner Apple Jack Daytime Sailing Cruise offers an excellent way to enjoy Maine’s coastline without breaking the bank. The boat’s historic charm, combined with the knowledgeable crew’s friendliness and the chance to see local wildlife, makes for a memorable outing. It’s a wonderful choice for families, couples, or solo travelers looking for an authentic maritime experience that’s relaxed, scenic, and fun.

While it’s a short trip, it packs enough sights, stories, and breezes to leave a lasting impression. If you enjoy the idea of sailing on Maine’s waters, spotting eagles and porpoises, and learning about local history, this cruise will likely meet your expectations. Just remember to bring your hat, sunscreen, and a smile — Maine’s sea air is as invigorating as it is beautiful.

FAQ

How long is the cruise?
The cruise lasts approximately 2 hours, providing a relaxed yet engaging window to enjoy the scenery and wildlife.

What is included in the price?
Your ticket grants you access to the sailing, and there’s a restroom onboard. You can purchase alcohol during the trip, but bringing your own food and non-alcoholic drinks is encouraged.

Do I need to book in advance?
Yes, booking ahead is recommended. You can also reserve now and pay later, with free cancellation available up to 24 hours before the trip.

Is the boat accessible for all?
The information provided doesn’t detail accessibility features, but since it’s a traditional schooner, it may have some limitations. It’s best to contact the provider if you have specific accessibility concerns.

Can I help with sailing the boat?
Yes, volunteers are often welcomed to help hoist sails or steer, making the experience more interactive.

What should I wear?
Dress comfortably for the weather. A hat, sunscreen, and a jacket are recommended, especially if the day is breezy or cool.

Whether you’re a seasoned sailor or a landlubber, this authentic Maine sailing adventure offers beautiful views, wildlife sightings, and a taste of maritime history that’s hard to beat.

You can check availability for your dates here: