Schooner Lazy Jack: Sail Boothbay Harbor's Oldest

Embark on a 2-hour sail aboard Boothbay Harbor’s oldest windjammer. Spot wildlife, explore islands, and experience Maine’s maritime charm.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Boothbay Harbor Region - Maine might be one of the finest cruising areas globally, offering a perfect blend of ocean sailing, coastal island adventures, and breathtaking mountain scenery. Wildlife sightings are frequent.
What's Included
  • BYOB drinks & snacks (non-alcoholic)
  • On-board restrooms
What's Not Included
  • Gratuities
  • Alcoholic beverages
Additional Information

Welcome aboard the Schooner Lazy Jack in Boothbay Harbor; your Maine vacation begins here! Join the crew for a 2-hour day sail on Boothbay Harbor’s oldest windjammer. You can help hoist the sails or even take a turn at the wheel as we navigate past Burnt Island Light, Squirrel Island, Ram Island Light, and the outer islands of Boothbay. Keep an eye out…

Location
20 Commercial St
Commercial Street
Please proceed to the Eastwind booth situated on the left side of the parking lot at Fisherman's Wharf near Pier 6 for check-in. Once checked in, for Apple Jack, our staff will direct you to a holding area, and a crew member will escort you to Pier 1, where Apple Jack is docked.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.2
(25 Ratings)
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Irenebg7402ad
Jul 20, 2025
The Schooner adventure - We had never been on a schooner before and we were so excited to be able to do this. The ship was sooo beautiful, they do not make ships like this anymore, it truly is a thing of beauty. Kate and Christina were awesome and so informative about sailing and all the landmarks around us. We saw different types of water fowl and even a seal came to visit.. It was the perfect day.
Review provided by Tripadvisor
Mariejos_ep298
Jul 16, 2025
I recommend - Wowwww, Katy and Bryan were really great , great as an activity to do in Boothbay! We also liked the effect that there are only 14 of us on the sailboat ............
Review provided by Tripadvisor
John
Jul 8, 2025
Wonderful Summer Cruise - Great afternoon cruise around Boothbay Harbor. The crew was professional, informative, and even funny at times. It was fun to learn the history of the ship which was older than me ( in my late 70’s) but still looked like it was in top shape and handled well. As a sailor in the past, it was really fun to get out on the water again with a crew that could handle a double masted ship that well. I highly recommend this tour.
Review provided by Tripadvisor
L0vingfam
Oct 7, 2024
A don't miss experience! - I am a sailor and was very impressed. Wonderful sail with beautiful views and capable, friendly captain and crew. Loved every minute of it!
Review provided by Tripadvisor
658davidk
Oct 6, 2024
Wonderful sail - Wonderful sail It was a partly cloudy afternoon, temperature in the 60’s. Captain Katie explained the safety rules and features and we got underway. The communications between Katie and her crew (Marison, also a certified captain) were systematic and unambiguous, showing us that we were in excellent hands. We motored out of the inner harbor and found a lovely moderate wind on the bay. They set the sails and we tacked out past Squirrel Island with captain Katie and Marison providing pertinent narration and answers to questions we had. It was a totally pleasant experience.
Review provided by Tripadvisor
Donna
Sep 13, 2024
Had a wonderful sail on the Apple Jack - Had a great 2 hour tour on the Apple Jack schooner. Captain Katie kept us entertained with great stories and tales. The weather was perfect and even saw a loon and a seal. Highly recommended!
Review provided by Tripadvisor
E919fgshannonm
Sep 7, 2024
Wonderful trip in the Apple Jack - Great tour and fun sailing aboard the Apple Jack. Crew did a fantastic job setting the sails and navigating us out to the lighthouse and back. Great information about sailing on schooners and the history and fun stories about Boothbay Harbor. Saw some seals and the porpoise swam along side us.
Review provided by Tripadvisor
Ddolson
Jul 6, 2025
Fun smooth sail with friendly crew. - Fun smooth sail with friendly crew. Great break for our family from walking around the town and a nice way to see more of the harbor.
Review provided by Tripadvisor
Paradise22085323617
Oct 19, 2024
Nice, but going nowhere - Nice boat, very friendly crew, but the boat went nowhere. It remained in the middle of the sea for about an hour. Maybe that is what was supposed to be, just the experience of sailing with a schooner, maybe my expectations of going to see the coast were unreasonable
Review provided by Tripadvisor
Melinda_l
Jun 8, 2025
Not As Expected - This is not a narrated tour. You basically sail around the harbor area. They did ask for participants to help raise the sails, which was cool.
Review provided by Viator
From $55
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).