A Friendly Look at the Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
If you’re dreaming of sailing along Maine’s scenic coastline, this 2-hour day sail on the Schooner Applejack offers a genuinely laid-back way to soak in the views and enjoy the fresh ocean air. While we haven’t been on this particular trip ourselves, reviews and descriptions paint a picture of a charming, accessible experience perfect for those wanting a taste of classic Maine sailing.
What really draws us in are how much you can participate—helping hoist sails or taking the wheel—making it more than just a sightseeing trip. Plus, the chance to spot local wildlife like porpoises, bald eagles, and harbor seals really helps bring the scenery to life.
That said, this is a shorter, relaxed sail, so if you’re after a full-day adventure or intense sailing, this might feel a bit light. Still, it’s well-suited for visitors who want a gentle, scenic outing that mixes history, wildlife, and some hands-on fun. It’s perfect for travelers who appreciate authenticity, stunning coastal views, and a bit of maritime history without the fuss.
Key Points

- Short but sweet: Around 2 hours, making it easy to fit into a busy day or combine with other activities.
- Hands-on experience: You can help hoist sails or steer, which adds a fun, interactive element.
- Wildlife sightings: Expect to see porpoises, osprey, bald eagles, and seals—nature lovers will appreciate this.
- Inclusion of snacks and restroom: Bring your own drinks or snacks; a restroom is available onboard.
- Affordable value: At around $55 per person, it offers a lot of the Maine sailing experience without a hefty price tag.
- Limited group size: With a maximum of 14 travelers, it feels intimate but not crowded.
Introduction to the Experience
Sailing on the Schooner Applejack in Boothbay Harbor is a simple yet charming way to connect with Maine’s coastal beauty. This 2-hour sail promises a relaxed atmosphere, friendly crew, and plenty of chances to enjoy the scenery without feeling rushed.
Two things really stand out about this experience. First, the interactive nature—you’re encouraged to help with the sails or take the wheel, which makes the trip feel more genuine and engaging. Second, the potential for wildlife sightings—from playful porpoises to soaring eagles—adds a special touch that appeals to nature buffs and casual observers alike.
On the flip side, a potential drawback is the weather dependency—good weather is crucial, and if the wind isn’t cooperative, the experience might be more subdued or subject to cancellation. It’s also a short trip, so if you’re craving a full day on the water, this might leave you wanting more.
This sail is best suited for travelers who want an authentic, manageable way to enjoy Maine’s coast, especially if they’re interested in hands-on sailing and wildlife viewing but aren’t looking for a lengthy or intense adventure.
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All About the Itinerary

Starting Point and Setting
The tour kicks off at 20 Commercial St in Boothbay Harbor. From here, you step aboard the Schooner Lazy Jack, a vessel that’s steeped in local maritime charm. As the boat begins to glide out into the harbor, the real magic starts.
The Voyage Out
During this sail, you’ll head past Burnt Island Light, Squirrel Island, Ram Island Light, and the outer islands of Boothbay. These landmarks are classic Maine maritime icons, and being out on the water makes their details more vivid.
Wildlife and Scenic Highlights
The crew keeps a sharp eye out for porpoises, which are often playful and can surface right alongside the boat. You might see Osprey, Bald Eagles, or harbor seals lounging on rocks or popping up nearby. Several reviews highlight this aspect, with one noting that the “excellent experience” was partly thanks to “beautiful boat and wonderful crew.”
The Sails and Hands-On Fun
One of the most praised parts of this sail is the opportunity to get involved with hoisting sails and taking the wheel. This isn’t just a sightseeing cruise—it’s a chance to step into the role of sailor, even if just for a little while. As one reviewer said, watching the crew work the sails “brought the schooner alive,” which adds a layer of authenticity.
Return and Reflection
After about two hours, the boat gently makes its way back to the harbor. The experience ends right where it began, leaving you with memories of a breezy, scenic adventure and hopefully some good photos.
What You Can Expect Onboard

Crew and Atmosphere
The crew is described as “wonderful” and “friendly,” making the whole experience feel welcoming. They’re experienced, and their enthusiasm helps everyone feel comfortable participating in the sailing tasks.
Group Size and Intimacy
With a cap of 14 travelers, this sail maintains an intimate feel without being crowded. You’ll have plenty of space to move around or just relax and take in the views.
Comfort and Convenience
The boat features a restroom, so you won’t have to worry about comfort. You’re encouraged to bring your own snacks and drinks—non-alcoholic beverages are recommended, though beer, wine, and liquor are available for purchase if you want to indulge.
Weather and Cancellation
As with most outdoor activities, good weather is essential. If the weather turns poor, the tour might be canceled or rescheduled, with a full refund or alternative date offered. This flexibility is good to know beforehand.
The Value of the Experience
At $54.95 per person, this sail offers a relatively affordable way to experience Maine’s coast authentically. Considering the interactive hands-on element, the wildlife sightings, and the scenic routes, many travelers find the value pretty good. It’s not a full-day extravaganza—more of a quick, relaxing escape—but one that can fit easily into a day of sightseeing.
The reviews suggest that this experience is appreciated for its balance of relaxation and activity. The opportunity to steer or hoist sails, combined with the chance to spot wildlife, makes it more memorable than a passive cruise.
Who Should Consider This Sail?
This trip is tailored for those who enjoy gentle adventures, scenic views, and a touch of maritime history. It’s perfect if you’re visiting Boothbay Harbor and want a laid-back experience with a bit of hands-on sailing.
It’s also a good choice if you’re traveling with a small group or looking for a more personal, less commercial feel in your boat ride. Wildlife lovers will appreciate the chance to see porpoises and eagles, while those interested in Maine’s nautical heritage will enjoy being on a classic windjammer.
If you’re flexible with weather and don’t mind a shorter trip, this sail offers a genuine Maine maritime experience without the cost or commitment of longer cruises.
Final Thoughts
The Schooner Applejack 2-Hour Day Sail provides a straightforward, enjoyable introduction to Maine’s coastal waters. It’s an experience well-suited for travelers who want to combine scenic beauty with some active participation—you might find yourself hoisting sails or steering the schooner, all while taking in spectacular views.
While it’s not designed for those seeking a long or intense sailing adventure, it’s ideal for visitors craving a relaxing, authentic maritime outing that offers excellent wildlife sightings and friendly company. The affordability and intimate group size add to its appeal, making it a worthwhile choice for a memorable day on the water.
Overall, if you enjoy maritime scenery, wildlife spotting, and the chance to get involved in sailing, this trip is well worth considering—especially on a calm, clear day when the wind is just right.
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor
“Excellent experience! Would recommend to anyone! Beautiful boat and wonderful crew! We enjoyed the cool air and the length of the journey! We also …”
FAQ
How long is the sail?
It lasts approximately 2 hours, making it a manageable break from other sightseeing activities.
What is included in the price?
The ticket covers the sail itself, with a restroom onboard. You can bring your own non-alcoholic drinks and snacks.
Can I bring alcohol?
Alcoholic beverages are available for purchase on board, but the fare itself only includes non-alcoholic drinks and snacks you bring.
Is this experience suitable for children?
Most travelers can participate, but the tour is better suited for those comfortable on boats and with moderate activity levels.
What kind of wildlife might I see?
Expect to see porpoises, osprey, bald eagles, and harbor seals, based on the reviews and common sightings in the area.
What if the weather is bad?
The tour is weather-dependent. If canceled due to poor weather, you’ll be offered a different date or a full refund.
How many people are on each trip?
The maximum group size is 14 travelers, ensuring a more personal experience.
Where do I meet for the tour?
The meeting point is 20 Commercial St in Boothbay Harbor.
Is there a minimum number of travelers?
Yes, if the minimum isn’t met, the trip might be canceled or rescheduled with options for a refund or alternative date.
Do I need to book in advance?
Yes, most travelers book about 32 days ahead on average, which helps secure a spot during busy seasons.
If you’re after a simple, authentic Maine sailing experience that combines scenic views, wildlife, and active participation, the Applejack Day Sail could be just the ticket. It offers a taste of maritime life, friendly crew, and the chance to breathe in that crisp coastal air—perfect for a relaxed day by the sea.


