Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

Sailing along Maine’s rugged coast offers a rare chance to see its natural beauty from a perspective few get — the water. The Schooner Apple Jack Daytime Sailing Cruise in Boothbay Harbor promises a gentle, engaging ride that takes you past iconic lighthouses, remote islands, and bustling lobster boats. This review explores what makes this trip stand out, along with practical tips to make your experience unforgettable.

We love how this cruise combines spectacular scenery with a friendly, knowledgeable crew that makes you feel like a guest in their maritime world. Plus, the chance to see wildlife such as porpoises and bald eagles adds a lively touch to the peaceful voyage. On the downside, the two-hour duration might leave those craving a longer adventure wanting more—though it’s perfect for a relaxed taste of Maine’s coast. If you enjoy authentic, hands-on experiences with a touch of maritime history, this cruise is ideal for families, first-time visitors, or anyone eager to see Maine from a different angle.

Key Points

• Stunning coastal views of Maine’s rugged shoreline, lighthouses, and islands.
• Engaging crew that shares local stories, making the trip both entertaining and educational.
• Wildlife sightings including porpoises, bald eagles, and harbor seals.
• Historic schooner experience on Boothbay’s oldest windjammer.
• Affordable price point at $55 per person for two hours of sailing.
• Ideal for all ages and those looking for a relaxed, scenic outing.

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An Authentic Maine Sailing Experience

The Apple Jack schooner offers an experience rooted in Maine’s maritime tradition. As the sails are hoisted, you can’t help but feel a sense of anticipation. There’s a quiet thrill in watching the old vessel glide away from the dock, its sails billowing in the breeze. The gentle rocking, combined with the sound of water lapping against the hull, sets a relaxing tone.

The boat itself is Boothbay’s oldest windjammer, which adds a layer of authenticity and charm. Its weathered wood and classic design immediately evoke a sense of stepping back in time — a perfect backdrop for appreciating Maine’s maritime culture. This vessel isn’t just a boat; it’s a moving piece of local history.

What’s Included and What to Bring

For just $55 per person, the ticket covers your two-hour sailing adventure. Restrooms are available onboard — a thoughtful touch for comfort — and you can purchase alcohol, including beer, wine, and cocktails, if you want to toast the scenery. However, you’ll need to bring your own food and non-alcoholic drinks. This makes it a flexible option for picnickers or those wanting to sip a local brew with the salty air.

It’s worth noting that gratuities are not included, so if you’re pleased with your crew’s efforts, a tip is appreciated but not expected. The meeting spot is clearly marked by a Schooner Eastwind Boarding sign at Fisherman’s Wharf Inn parking lot, making check-in straightforward.

The Itinerary: What You’ll See and Do

The cruise begins with the crew raising the sails, an engaging process that often invites volunteers to help out. The setting sail marks the start of a scenic journey into Maine’s coastal waters. You’ll cruise past Burnt Island Light, an iconic lighthouse offering a glimpse into the maritime navigation that keeps the coast safe. The crew’s commentary brings these sights to life, often sharing stories or interesting facts, which reviewers praise as “friendly and knowledgeable” guides.

Next, the boat glides past Squirrel Island and Ram Island Light, where the views of coastal homes and remote islands are truly special — sights accessible only by boat. These spots seem to belong to a different world, showcasing Maine’s natural and human history in a quiet, unspoiled setting.

Wildlife is a highlight as well. Travelers frequently spot porpoises, harbor seals, and bald eagles, adding a lively dimension to the trip. One reviewer notes, “We saw so many porpoises — it was like watching playful dolphins,” encapsulating the sense of wonder you might experience.

The cruise also offers a charming view of local lobster boats, busy hauling in their catches — a quintessential Maine scene that connects you to the day-to-day life of the coast.

The Crew: Knowledgeable and Friendly

Multiple reviews emphasize the crew’s friendly, engaging nature. Captain Josh and Christina, for instance, are praised for their informative commentary and approachability, making everyone feel involved. One reviewer mentioned, “They made the sailing experience relaxing and fun,” highlighting how the crew’s enthusiasm enhances the trip.

The crew also invites volunteers to help hoist sails or steer, adding a participatory element that appeals to those wanting more than just passive sightseeing. It’s a great way to connect with the boat and its history, especially for families or groups who enjoy hands-on adventure.

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The Price and Value

Considering the $55 ticket price for a two-hour outing, this cruise offers genuine value for money. It’s an affordable way to enjoy Maine’s coast with minimal fuss, especially given the included amenities like onboard restrooms and the opportunity to purchase drinks. The reviews consistently describe it as “a relaxing, beautiful day on the water,” which makes it seem like a worthwhile investment.

The size of the group is kept comfortable, often around ten passengers plus crew, which ensures a cozy, intimate atmosphere. You won’t feel crowded or rushed, and the small group allows for better interaction with the crew and more personalized stories.

Who Will Enjoy This Cruise?

If you’re looking for a calm, scenic excursion that combines history, wildlife, and coastal views, this tour fits the bill. It’s perfect for families, couples, or solo travelers wanting a taste of Maine’s maritime life. It’s also suitable for those who appreciate authentic sailing experiences, as opposed to large, commercial cruises.

For those curious about lighthouses, islands, and lobster boats, this cruise delivers close-up views and storytelling that bring the coast alive. However, if you prefer a longer or more adventure-oriented trip, or want to circumnavigate islands, you might find this slightly limited in scope.

Practical Tips for Travelers

Dress comfortably with layers, as the weather can change quickly on the water. A hat and sunscreen are essential for daytime trips, and a light jacket can keep you warm if it gets breezy. Since alcohol is available for purchase, bringing cash or cards is advisable.

Remember to arrive at least 15 minutes early for check-in, and bring your own food and drinks if desired. The trip operates rain or shine, so check the weather forecast beforehand and dress accordingly.

The Sum Up: Who Should Book This Experience?

This two-hour schooner cruise offers a beautiful, authentic taste of Maine’s coast without breaking the bank. It’s a wonderful choice for travelers who want a relaxed, scenic outing with a friendly crew sharing local stories. The combination of stunning views, wildlife sightings, and maritime history makes it a memorable addition to any itinerary.

If you’re after a peaceful escape, want to learn about Maine’s nautical heritage, or enjoy seeing wildlife up close, this cruise will meet and often exceed your expectations. It’s especially well-suited for those traveling with families, couples, or solo adventurers eager to connect with Maine’s maritime soul.

The Apple Jack Daytime Sailing Cruise is an authentic, high-value outing that delivers plenty of memorable moments in just two hours — a true highlight of any trip to Boothbay Harbor.

FAQ

What is the duration of the cruise?
It lasts about 2 hours, making it a manageable and relaxing outing.

Can I help with the sails?
Yes, volunteers are often invited to hoist sails or steer, depending on the crew’s discretion.

Is the trip suitable for children?
Yes, many reviews mention taking children on the trip, especially since it’s a gentle, scenic cruise with engaging storytelling.

Are drinks and snacks available onboard?
Soft drinks, beer, wine, and cocktails are available for purchase; you should bring your own food and non-alcoholic drinks.

Where do I meet the boat?
At the Fisherman’s Wharf Inn parking lot, marked by a Schooner Eastwind Boarding sign.

Is there a restroom onboard?
Yes, restrooms are available, which is a considerate feature for a 2-hour trip.

What should I bring?
Dress in layers, bring sunscreen, a hat, and a jacket to stay comfortable.

Can I cancel my booking?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is there a minimum group size?
While not explicitly stated, reviews suggest small groups, typically around ten passengers for a cozy experience.

Is the crew friendly and knowledgeable?
Absolutely — reviews consistently praise the crew’s friendliness, local knowledge, and engaging manner.

In essence, the Schooner Apple Jack Daytime Sailing Cruise offers a genuine, affordable, and thoroughly enjoyable way to soak in Maine’s scenic coast. Whether you’re a first-time visitor or a seasoned sailor, this trip provides a peaceful yet vivid glimpse into the maritime charm that defines Boothbay Harbor.

You can check availability for your dates here: More Great Tours Nearby