Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

Taking to the water on a classic schooner in Boothbay Harbor offers an authentic and scenic way to explore Maine’s rugged coast. This 2-hour cruise on the historic Schooner Apple Jack promises stunning views of lighthouse-laden islands, chances to spot porpoises and bald eagles, and a taste of Maine maritime tradition. Whether you’re a seasoned sailor or a first-time boatgoer, this trip delivers a relaxed, informative, and picturesque experience.

What we love most about this tour is its blend of natural beauty and maritime history, all wrapped up in an intimate, friendly setting. The knowledgeable crew, led by the charismatic Captain Shawn and First Mate Megan, makes the journey engaging without overwhelming. A potential consideration is that, being a daytime cruise, it’s best suited for those who enjoy bright, sunny weather and clear views — weather can influence the experience if clouds roll in.

This cruise is ideal for travelers seeking a laid-back yet immersive way to see Maine’s coastal highlights without the crowds or formality of larger tours. It’s perfect for families, couples, or solo adventurers who appreciate a mix of scenic sailing, wildlife watching, and learning about the local maritime landscape.

Key Points

• Authentic Sailing Experience: Sail on Boothbay’s oldest windjammer with a crew that’s both knowledgeable and personable.
• Stunning Coastal Views: See lighthouse islands, remote coves, and sea life only visible by boat.
• Wildlife Spotting Opportunities: Look out for porpoises, bald eagles, osprey, and seals.
• Interactive & Relaxed: Help hoist sails or take the wheel if you want to get involved.
• Great Value: At $55 per person, it’s a reasonably priced way to enjoy a unique Maine maritime experience.
• Family & Solo Friendly: Small groups and an intimate atmosphere make it suitable for all travelers.

Detailed Review of the Schooner Apple Jack Daytime Sailing Cruise

What the Experience Is Like

From the moment you arrive at the Fisherman’s Wharf Inn parking lot, marked by a prominent Schooner Eastwind sign, there’s an immediate sense that you’re about to step into a classic Maine adventure. As the crew prepares the schooner, you’ll notice how well-maintained and charming the vessel is — a true piece of maritime history, being Boothbay’s oldest windjammer.

Once aboard, the feeling of anticipation grows as the crew hoists the sails, filling the air with the fresh scent of salt and canvas. The gentle sway of the schooner and the rhythmic lapping of waves against the hull set a peaceful mood. The captain, Shawn, and first mate Megan, are praised for their warmth, expertise, and good humor, making everyone feel welcome whether they’re experienced sailors or first-timers.

The cruise kicks off with a slow glide out of Boothbay Harbor, revealing sweeping views of rugged cliffs, colorful lighthouse towers, and quaint waterfront homes rarely seen from land. It’s a chance to appreciate Maine’s maritime charm from a vantage point that’s both intimate and expansive.

The Highlights Along the Route

Burnt Island Light: A major highlight is passing Burnt Island Light, which is visible from the water and offers a classic Maine lighthouse photo op. As you approach, the crew shares stories about Maine’s lighthouse history, adding depth to the scenery.

Remote Islands & Coastal Homes: The boat drifts past Squirrel Island, Ram Island Light, and other tiny islands that are only visible from the sea. Many of these spots are home to summer cottages and fishing retreats, giving you a glimpse into local life.

Wildlife Watching: The crew’s keen eyes often spot porpoises playing in the wake, while the overhead view might reveal soaring bald eagles or osprey nests. Reviewers mention seeing harbor seals lazily lounging on rocks, adding to the sense of being in a living, breathing ecosystem.

Local Boats & Lobster Traps: Watching the lobster boats hauling traps or setting pots brings Maine’s working waterfront into focus. It’s a reminder of how intertwined the local economy is with the sea.

What Makes It Special

The knowledgeable crew truly elevates this experience. Reviewers rave about Captain Shawn and Megan, who are described as friendly, humorous, and eager to share their maritime expertise. One reviewer, Glenn, noted that as a solo offshore sailor, he appreciated the historic charm of the schooner and the chance to sail on a vessel with real character.

Participants are encouraged to take an active role, whether helping hoist sails or steering the boat, which enhances the sense of connection and fun. The small group size — around ten guests — ensures plenty of personal attention and space to ask questions or simply relax.

The Practical Stuff

Price & Value: At $55 per person, this tour offers excellent value considering the intimacy, scenic beauty, and expert guidance. For this price, you get a true sailing experience without the crowds or commercial feel of larger tours.

Duration & Timing: Lasting two hours, it’s a perfect length to enjoy the scenery without feeling rushed. Check the schedule for available start times, which vary seasonally.

Onboard Amenities: Restrooms are available, and you can purchase drinks like beer, wine, or soft drinks onboard. Bring along your own food and non-alcoholic beverages if you prefer a picnic at sea.

Weather Considerations: The tour is weather-dependent; a clear, sunny day will really let you soak in the sights. Cloudy or rainy weather might dull the views, but the crew does their best to keep everyone comfortable and informed.

Who This Tour Suits Best

This cruise is perfect for those looking for a relaxed, scenic voyage with a touch of maritime history. It’s well-suited for families, couples, solo travelers, or small groups seeking an authentic experience. Nature lovers will appreciate the wildlife sightings and the chance to see Maine’s coast from a different perspective.

If you enjoy engaging with knowledgeable guides, sailing on a historic vessel, or simply want a peaceful day on the water, this tour checks all those boxes. It’s also a great choice if you prefer a smaller, more intimate setting rather than crowded large boats or busy tour operators.

The Sum Up

The Boothbay Harbor Schooner Apple Jack Daytime Sailing Cruise offers a genuine slice of Maine’s maritime life. With its friendly crew, stunning scenery, and opportunities to spot wildlife, it provides more than just a boat ride — it’s an authentic experience that captures the spirit of the coast. For a reasonable price, you’ll enjoy a memorable two hours filled with beautiful vistas, lighthearted storytelling, and a sense of history.

This tour is especially well-suited for travelers who want to combine scenic beauty with a bit of hands-on sailing and cultural insight. It’s a peaceful, picturesque way to connect with Maine’s coast away from the crowds and commercial tours. Whether you’re a maritime enthusiast or simply seeking a relaxing day on the water, the Schooner Apple Jack is a charming choice.

FAQs

Is this tour suitable for children?
While the information doesn’t specify age restrictions, the small group size and relaxed pace make it a good option for families. Kids who enjoy boats and wildlife will likely love it, but check with the provider if you have very young children.

How long is the cruise?
The cruise lasts approximately 2 hours, making it a manageable outing without feeling too lengthy.

Are food and drinks included?
No, food and non-alcoholic beverages should be brought along, but onboard drinks like beer, wine, and soft drinks are available for purchase.

Can I help with sailing during the tour?
Yes, volunteers are encouraged to help hoist sails and steer, adding an interactive element to the experience.

Where do I meet for the cruise?
The meeting point is marked by a prominent Schooner Eastwind Boarding sign at the Fisherman’s Wharf Inn parking lot, to the right and behind the ticket booth.

Is the tour weather-dependent?
Yes, the tour relies on good weather to provide the best views. It’s advisable to check the forecast and be prepared with a hat, sunscreen, and a jacket.

In summary, the Boothbay Harbor Schooner Apple Jack Daytime Sailing Cruise provides a charming, authentic look at Maine’s coast, blending scenic beauty, wildlife, and maritime history. It’s an excellent option for travelers seeking a relaxed, intimate, and educational experience on the water in one of Maine’s most picturesque harbors.