Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

If you’re dreaming of slipping away on a classic Maine schooner, this Boothbay Harbor daytime sailing cruise might be just what you’re looking for. While I haven’t personally been on this exact trip, the glowing reviews and detailed descriptions suggest it’s a pretty special way to see the coast.

What makes this tour stand out? First, it’s a chance to sail on Boothbay’s oldest windjammer, which adds a sense of history and authenticity. Second, the crew is described as friendly and knowledgeable, often sharing stories and insights that make the experience feel personal. Lastly, the scenery—lighthouse views, tiny islands, and coastal homes—looks utterly captivating from the water.

That said, keep in mind that it’s a two-hour trip, so if you’re craving a longer adventure or more extensive exploration, this might not be enough. Also, bringing your own snacks and non-alcoholic drinks is recommended, so plan accordingly.

This experience is perfect for travelers who love nature, history, and scenic views but prefer a relaxed, guided sail instead of a strenuous excursion. Families, couples, or solo travelers seeking a taste of Maine’s maritime charm will find plenty to love.

Good To Know

• Authentic Experience: Sail on Boothbay’s oldest schooner with a knowledgeable crew.
• Scenic Views: See lighthouses, remote islands, and coastal homes only visible from the water.
• Wildlife Encounters: Watch for porpoises, bald eagles, and harbor seals.
• Value for Money: At $55, it offers a well-rounded, memorable coastal adventure.
• Interactive Sailing: Help hoist sails or steer the boat if you’re feeling adventurous.
• Comfort & Convenience: Restroom onboard and options to purchase drinks, with a clear meeting point.

You can check if your dates are available here:

An In-Depth Look at the Apple Jack Daytime Sailing Cruise

The Vessel and Its Historic Charm

Sailing aboard the Apple Jack, the oldest windjammer in Boothbay Harbor, is like stepping back in time. Many reviews highlight the vessel’s classic design and well-preserved condition, which adds a layer of authenticity to the trip. The boat’s weathered but sturdy appearance suggests durability and history—perfect for those who appreciate maritime character.

Knowing you’re on a vessel with a storied past enhances the experience. As the crew hoists the sails, you can’t help but feel a sense of connection to the generations of sailors who’ve navigated these waters. The sound of the wind filling the sails and the gentle rocking of the boat create a tranquil, almost meditative atmosphere that many find deeply relaxing.

The Itinerary: What You’ll See and Do

The cruise begins at Fishermans Wharf Inn, marked clearly by a prominent Schooner Eastwind Boarding sign. Once aboard, the crew—known for being friendly and engaging—starts sharing stories about the local area, making the journey informative as well as scenic.

As the sails are raised, the boat begins to glide smoothly through the harbor. The first sights are the iconic Burnt Island Light, visible from the water and a favorite among visitors for its photogenic charm. From there, the route takes you past Squirrel Island, a tiny, remote island only accessible by boat, providing unique photo opportunities and a chance to appreciate the rugged Maine coastline.

Another highlight is the chance to see local boats catching lobsters—a real-life glimpse of Maine’s lobstering industry. Reviewers mention how the crew often points out these sights, adding context and local color.

Wildlife and Nature Encounters

Wildlife sightings are a key part of this cruise. Expect to see porpoises, bald eagles, osprey, and harbor seals—all frequently spotted from the boat. Several reviews emphasize how these encounters add excitement and a sense of connection with Maine’s natural environment.

One reviewer mentioned, “We saw plenty of porpoises and even a bald eagle soaring overhead,” which made the trip feel truly special. The crew’s attentiveness to wildlife and their knowledge about local habitats make these moments even more meaningful.

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Crew and Atmosphere

The crew, including Captain Josh and Christina, receive high praise for their friendliness and expertise. Multiple reviews mention how they’re eager to share stories and answer questions, making the experience feel personalized.

Guests often note how volunteers are encouraged to help hoist sails or steer, adding a hands-on element that appeals to those wanting a more active role. The overall vibe is described as relaxed, fun, and engaging, with a good balance of informative commentary and free time to soak in the scenery.

Comfort and Facilities

The boat is equipped with a restroom onboard, which is always appreciated during a two-hour excursion. You might also want to bring a hat, sunscreen, and a light jacket, as per recommendations, to stay comfortable in Maine’s variable weather.

While alcohol isn’t included in the ticket price, guests can purchase drinks onboard, including beer, wine, and soft drinks. Many reviewers appreciated having this option, especially as they relaxed and enjoyed the views.

Pricing and Value

At $55 per person, this cruise offers solid value for a two-hour scenic sail. For the price, you get a chance to see iconic Maine landmarks, spot wildlife, and learn about the local area from friendly, experienced guides.

Considering the boat’s historic significance and the quality of the crew, many feel that this trip provides a memorable experience comparable to more expensive tours. The opportunity to participate actively in sailing also adds a layer of engagement that many travelers value highly.

Practical Details and Booking

The meeting point is straightforward—just look for the Schooner Eastwind Boarding sign at Fishermans Wharf Inn parking lot. Booking is flexible with options to reserve now and pay later, plus free cancellation up to 24 hours in advance.

Trips are generally available in the morning and afternoon, making it easy to fit into most travel plans. Since the tour is in English, non-native speakers should have no trouble following along.

Who Should Consider This Tour?

This cruise appeals to a wide range of travelers. Families with children (ages 11 and up, as noted in reviews), couples seeking a romantic yet laid-back experience, or solo travelers eager for a peaceful day on the water will all find value here.

It’s ideal for those who appreciate authentic, intimate boat experiences over large cruise ships or overly commercialized tours. If you’re craving a quick but meaningful glimpse of Maine’s coast, with plenty of chances for wildlife spotting and photo ops, this trip delivers.

The Sum Up

The Boothbay Harbor Schooner Apple Jack Daytime Sailing Cruise offers a beautiful, engaging, and well-priced way to experience Maine’s coastal scenery. Its blend of historic charm, friendly crew, and wildlife encounters makes it a standout activity for anyone wanting a genuine taste of the region.

You’ll love the views of lighthouses and islands, the chance to learn about local maritime life, and the relaxed, friendly atmosphere onboard. Plus, the option to help hoist sails or steer adds a memorable touch that keeps the trip lively and hands-on.

While it’s a shorter adventure, the authentic experience and stunning scenery ensure it’s a worthwhile addition to any Maine itinerary. It’s especially well-suited for travelers who enjoy nature, history, and authentic maritime culture without a hefty price tag.

If you’re looking for a scenic, peaceful, and fun sail in Boothbay Harbor, this tour delivers in every way.

FAQs

• How long is the cruise?

The cruise lasts about 2 hours, offering a relaxed but engaging experience.

• What is the meeting point?

The meeting point is marked by a prominent Schooner Eastwind Boarding sign in the Fishermans Wharf Inn parking lot.

• Can I buy drinks onboard?

Yes, alcohol and soft drinks are available for purchase during the trip.

• Is food provided?

No, food and non-alcoholic beverages are not included, so bring your own if you’d like to snack.

• Are there restroom facilities onboard?

Yes, the boat has a restroom for passenger convenience.

• Can I participate in sailing activities?

Yes, guests are encouraged to help hoist sails or steer, depending on the crew’s instructions and your comfort.

• Is this tour suitable for children?

Yes, many reviews mention bringing children aged 11 and older, who enjoyed the experience.

• What kind of wildlife might I see?

Expect to spot porpoises, bald eagles, osprey, and harbor seals.

• How much does it cost?

The ticket price is $55 per person, which many reviewers find very reasonable for the value.

• Do I need to book in advance?

It’s recommended to reserve ahead, but you can also choose to pay later with flexible booking options. Cancellation is free up to 24 hours beforehand.

This schooner cruise offers an authentic, scenic voyage into Maine’s coast, perfect for travelers seeking a blend of wildlife, history, and maritime charm—all at a friendly price.

You can check if your dates are available here: