Sailing in Boothbay Harbor on the schooner Apple Jack offers a delightful way to explore Maine’s rugged coastline. For just $55 per person, you’ll embark on a 2-hour trip that promises scenic vistas, wildlife encounters, and a dash of nautical history. The trip takes you past Burnt Island Light, Squirrel Island, and other remote islands only visible from the water, giving you a perspective that’s impossible to get from land.
What excites us most about this experience is how knowledgeable and friendly the crew is—reviewers consistently praise the guides for making the trip both educational and fun. Plus, the classic old schooner itself is a joy to sail on, evoking the golden age of Maine’s maritime past. On the flip side, since this is a daytime cruise, if you’re hoping for sunset views or a longer voyage, you might find this trip a bit shorter than some other options.
This cruise suits travelers who love authentic maritime experiences, enjoy wildlife watching, and appreciate scenic coastal landscapes. It’s perfect for families, couples, or groups wanting a relaxed, engaging outing that combines history, nature, and a touch of adventure.
Key Points

- Authentic schooner experience on Boothbay’s oldest windjammer, Apple Jack.
- Wildlife sightings including porpoises, bald eagles, and harbor seals.
- Scenic views of lighthouses, islands, and coastal homes only accessible by boat.
- Knowledgeable crew that shares engaging stories and info about the area.
- Affordable value for a memorable Maine day on the water.
- Flexible booking with free cancellation up to 24 hours in advance.
Discovering the Maine Coast on a Classic Schooner

Sailing on the Apple Jack, Maine’s oldest windjammer, feels like stepping back in time. The vessel’s weathered wooden hull and traditional rigging are beautiful reminders of the state’s seafaring heritage. As we set off from the dock, the crew expertly hoists the sails with a rhythm that’s both efficient and charming. There’s something inherently satisfying about watching the sails catch the breeze, propelling you smoothly into the harbor.
Once underway, the gentle hum of the wind fills the air, and the rhythmic lapping of water against the hull becomes your soundtrack. We loved the way the crew made everyone feel involved—helping hoist sails or taking a turn at the wheel. It’s a hands-on experience that turns passengers into part of the crew for a brief but memorable stretch.
Planning more time in Boothbay Harbor? We've covered other experiences worth considering.
The Scenic Route and Key Landmarks

The main sights along the route are lighthouses, islands, and coastal homes that only reveal themselves from the water. Passing Burnt Island Light is a highlight—its striking red and white tower standing guard over the entrance to Boothbay Harbor. The view of Squirrel Island and Ram Island Light offers a perspective few visitors get, making the trip feel exclusive and special.
The trip’s itinerary also includes passing by outer islands of Boothbay, which are largely uninhabited but boast rugged beauty. These remote spots are perfect for wildlife viewing. According to reviews, you might catch sight of porpoises playing in the water and bald eagles soaring overhead. The crew is attentive to spotting and pointing out these creatures, enriching the experience.
If you’re lucky, you’ll see harbor seals lounging on rocks or local boats busy with their daily lobster catch, giving you a lively window into Maine’s working harbor. The crew’s stories about the area’s maritime history and current life add an educational layer to the cruise, making it more than just a pretty ride.
What to Expect During the Cruise

The 2 hours fly by as you glide past scenic landmarks and enjoy the company of fellow travelers. The crew is known for their friendly and engaging attitude, often sharing interesting facts or stories. One reviewer noted, “Josh and Christina were so friendly and informative about the sites,” which highlights how personal and approachable the guides are.
The experience is relaxed—there’s no rush, and you’re encouraged to help with sails or simply sit back and enjoy the views. Since restrooms are available onboard, comfort isn’t sacrificed during this trip. You may also purchase alcoholic beverages or soft drinks to sip while taking in the scenery, although bringing your own food and beverages is encouraged for a more personalized experience.
Weather can influence your trip—sunscreen, hats, jackets are recommended, especially on sun-drenched or windy days. The crew ensures everyone is comfortable and safe, but remember, alcohol and drugs are not permitted onboard for safety reasons.
Authenticity and the Value of the Experience

For just $55, this cruise offers excellent value. It’s a relatively short trip, but that’s part of its charm—allowing you to experience a taste of Maine’s maritime life without committing to a full day at sea. Multiple reviews mention how “the trip was relaxing and enjoyable the entire time,” and how it’s “a great ride for the money.”
The small group size means you won’t feel overwhelmed or lost in a crowd, and volunteers get the chance to participate actively. Several guests appreciated the attention to detail from the crew, which contributed to a comfortable, engaging experience without feeling commercialized.
More Great Tours NearbyWho Will Appreciate This Tour?

This cruise is ideal for families with kids, couples looking for a romantic daytime outing, or anyone interested in Maine’s maritime culture. Nature lovers will enjoy wildlife sightings, while history buffs appreciate the stories about Maine’s coastal and maritime history. It’s also suitable for those who want a laid-back, scenic experience with friendly guides and a classic sailing vessel.
Final Thoughts
The Schooner Apple Jack Daytime Sailing Cruise offers a genuine taste of Maine’s coast, combining scenic beauty, wildlife, and maritime charm in a relaxed two-hour trip. The affordability and small-group feel mean you’ll get more personal attention and a more authentic experience than many larger, commercialized tours.
If you want to see Maine from a different perspective—close to the water, with knowledgeable guides pointing out lighthouse beacons and wildlife—this cruise is a fantastic choice. Plus, the chance to help hoist sails or steer the boat adds a dash of adventure that’s hard to beat.
This experience is best suited for travelers who enjoy scenic outdoor activities, value authentic local experiences, and appreciate the history and beauty of Maine’s coastline. Whether you’re traveling solo, as a couple, or with family, it’s a memorable way to spend a couple of hours on the water.
FAQ
How long is the cruise?
The cruise lasts approximately 2 hours, offering a good balance of sightseeing and relaxation without feeling too rushed.
What is the price?
It costs $55 per person, making it an affordable option for a scenic, engaging water trip.
Is there any food or drinks included?
No, food and non-alcoholic beverages are not included; you’re encouraged to bring your own. Alcohol is available for purchase onboard.
Are restroom facilities available?
Yes, there are restrooms onboard, ensuring you stay comfortable during the trip.
Can I participate in sailing activities?
Yes, you can help hoist the sails or take a turn at the wheel, making it a hands-on experience.
What should I bring?
Bring a hat, sunscreen, and a jacket—the weather can vary, and it’s best to be prepared. No alcohol or drugs are allowed onboard.
In summary, the Boothbay Harbor Schooner Apple Jack cruise offers a well-balanced, authentic maritime adventure packed with scenic views, wildlife, and engaging guides—all at a reasonable price. Whether you’re a first-time visitor or a seasoned sailor, it’s a good way to connect with Maine’s coastal charm and maritime heritage.
You can check availability for your dates here: