Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

Boothbay Harbor: Schooner Apple Jack Daytime Sailing Cruise

If you’re looking to experience the Maine coast from a unique vantage point, a daytime sailing cruise aboard the Schooner Apple Jack might just be the perfect choice. While I haven’t personally set sail on this boat, the glowing reviews and detailed descriptions paint a picture of a delightful adventure that’s both scenic and engaging. It’s a solid pick for those who appreciate maritime history, love being on the water, or simply want a relaxing way to see Boothbay Harbor’s picturesque landscape.

What really draws me to this cruise are the stunning views of remote islands and lighthouses—some only visible from the water—and the chance to spot local wildlife like porpoises and bald eagles. Plus, the fact that you get to sail on Boothbay’s oldest windjammer adds a historical touch that many boats can’t offer. On the flip side, it’s a shorter, two-hour trip, so if you’re after an in-depth exploration or a longer cruise, you might find this a bit limited. Still, for a laid-back morning or afternoon outing, it hits all the right notes.

This tour is well-suited for travelers who enjoy casual, scenic excursions and want to learn from friendly, knowledgeable crew members. Families with kids, couples, friends, or solo travelers who appreciate maritime charm will likely find this sail a memorable part of their Maine trip. Serious sailors or those wanting a more immersive experience might want to look for longer or more adventurous options, but for most, this cruise hits a sweet spot of comfort, scenery, and value.

You can check availability for your dates here:

Key Points

• Scenic views of remote islands and lighthouses only visible by boat offer a special perspective.
• Knowledgeable and friendly crew make the experience more engaging and relaxed.
• Wildlife sightings like porpoises, bald eagles, osprey, and harbor seals add an exciting touch.
• Historic schooner adds a layer of charm and authenticity to the trip.
• Affordable price point at $55 per person for two hours of sailing.
• Bring your own snacks and drinks to enjoy while cruising, as provisions are not included.

The Experience: What to Expect on the Schooner Apple Jack Cruise

Imagine the thrill of seeing the sails go up, feeling the wind catch them, and the gentle sway of a beautifully maintained schooner cutting through the water. That’s exactly what a two-hour sail in Boothbay Harbor promises. The crew takes pride in their work, not just as guides but as storytellers who can share insights about local sites and maritime life while keeping the trip lively and friendly.

Setting sail from Fisherman’s Wharf Inn, you’ll notice the prominent Schooner Eastwind Boarding sign—an easy marker. Once aboard, the crew will help you settle in, and you’ll quickly feel the calming rhythm that only sailing can bring. The boat itself is historic, being the oldest windjammer in Boothbay, which adds a touch of nostalgia and authenticity to the experience.

As you glide away from the dock, the views start unfolding—rugged coastline, quaint fishing villages, and the iconic Burnt Island Light gradually come into view. The crew actively encourages participation, so if you’re up for it, help hoist the sails or take a turn at the wheel. This hands-on approach is a big part of what makes the trip memorable, especially if you’re new to sailing.

One of the greatest pleasures of this cruise is the chance to see remote islands like Squirrel Island and Ram Island Light—places you’d miss if you were just driving by. The conversations with the crew add depth to the trip, especially when they point out local boats hauling lobster or share stories about the area’s maritime traditions. Expect a soothing soundtrack of water laps and wind, punctuated by the occasional shout of encouragement from the crew.

Highlights of the Boating Adventure

Scenic Islands and Lighthouses

The primary attractions are the views of Burnt Island Light, Squirrel Island, and Ram Island Light. These landmarks are not only picturesque but also tell stories of Maine’s maritime history. Watching the lighthouse’s steady beam on the horizon gives a timeless feel to the cruise.

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Wildlife Encounters

Many reviewers, including Stacey and Nancy, mention the wildlife sightings as a highlight. Porpoises are often seen playing in the water, while the bald eagles and ospreys soar overhead. Harbor seals might also pop up alongside the boat—these moments make the trip special for nature lovers.

The Crew and Atmosphere

Multiple reviews praise the friendly and knowledgeable crew. Captain Josh and Christina, in particular, are noted for their warmth and ability to share interesting facts without overwhelming. Their attentiveness makes you feel cared for without feeling rushed.

Historic Schooner Experience

Sailing on Boothbay’s oldest windjammer lends an authentic maritime vibe. You’ll feel like you’ve stepped back in time, especially when helping with sails or standing at the wheel, which many guests report as fun and engaging.

Value for Money

At $55 per person, this cruise is competitively priced. It’s a two-hour trip that combines sightseeing, light activity, and relaxing scenery, offering good value, especially considering the quality of the experience and the stunning sights.

Practical Details and Tips

Duration & Timing: The cruise lasts exactly two hours, usually available in the morning or afternoon. If you’re tight on time, this is a perfect window to fit into your day.

Meeting Point: The Schooner Eastwind boarding sign at Fisherman’s Wharf Inn parking lot makes it easy to locate. Arrive a bit early to get settled and perhaps chat with other travelers.

What to Bring: Pack a hat, sunscreen, and a light jacket—conditions can change quickly on the water. Since food and drinks aren’t included, bring snacks and non-alcoholic beverages to enjoy during the cruise.

Accessibility & Comfort: Restrooms are available onboard, and the boat isn’t very crowded (usually around 10 passengers plus crew), so it’s a relaxed environment.

Additional Info: You can cancel up to 24 hours in advance for a full refund, which adds some flexibility if your plans change. Booking now and paying later options give you peace of mind as you plan your trip.

The Value and Who This Tour Suits Best

This scenic sailing cruise offers a delightful blend of nature, history, and maritime charm. It’s a wonderful way to experience Boothbay Harbor without the hustle or fuss—perfect for anyone who appreciates gentle adventures and stunning vistas. The crew’s enthusiasm and local knowledge elevate the experience, making it educational and enjoyable simultaneously.

While it’s not a long or adrenaline-pumping ride, the relaxed pace and scenic highlights suit travelers looking for a calm, picturesque outing. Families with children can enjoy this trip as well, especially since the crew makes it engaging and interactive. However, it’s primarily designed as a sightseeing and leisure activity, so if you’re after a more adventurous or extended sailing experience, consider other options.

The price point of $55 is attractive, considering the inclusion of sailing, stunning views, and the chance to participate in sailing activities. The reviews consistently praise the value for money, noting that the trip is “relaxing and enjoyable” and “well worth the cost.”

Frequently Asked Questions

How long is the cruise?
The cruise lasts exactly two hours, making it a perfect short outing for a morning or afternoon.

Is this tour suitable for children?
Many reviews mention families enjoying the trip with kids aged 11 and 13, finding it fun and relaxing. The hands-on sailing activities can be engaging for children who like boats and nature.

Can I help with sailing?
Yes, volunteers are encouraged to help hoist sails or steer, which adds to the fun and connection to the vessel.

What should I bring?
Bring a hat, sunscreen, and a light jacket. Since food isn’t included, pack snacks and drinks if you like. Alcohol is available for purchase onboard.

Is there a restroom onboard?
Yes, a restroom is available during the cruise.

What landmarks will I see?
You’ll see Burnt Island Light, Squirrel Island, Ram Island Light, and possibly the outer islands of Boothbay. The crew also points out local lobster boats and wildlife.

What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund, providing some flexibility in planning.

Final Thoughts: Is This Cruise Right for You?

If you’re after a peaceful, scenic sail that offers a taste of Maine’s coastal beauty and maritime history, this cruise is a strong contender. It’s especially appealing if you enjoy being on the water, want to see iconic lighthouse and island views, and appreciate engaging, friendly guides. The price makes it accessible, and the small group size ensures a relaxed, personable experience.

On the other hand, if you’re looking for a longer, more adventurous, or action-packed boat ride, this might feel a bit limited. The two-hour duration doesn’t leave a lot of room for extensive exploration or high-energy activities. Still, for many, it hits the sweet spot of a memorable, picture-perfect outing in Boothbay Harbor.

Overall, it’s a well-reviewed, authentic sailing experience that balances scenery, history, and wildlife in a way that many travelers find charming and worthwhile. Whether you’re traveling solo, as a couple, or with family, this cruise can add a peaceful, scenic highlight to your Maine trip.

You can check availability for your dates here: