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
4.3
(35 Ratings)
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1 star
Gayle
Oct 5, 2025
A great way to enjoy Boothbay Harbor - We had a great sail with Captain Luke and Brian. The day was fine, the wind was fresh, and the crew was friendly and courteous. We even got to see the fog roll in towards the end of the sail! This is a great way to experience Boothbay Harbor.
Review provided by Tripadvisor
Yongesimmons
Sep 19, 2025
Couldn't get better! - Beautiful day, steady wind, and great captain and mate. The information about the area and what we were sailing past made the cruise more enjoyable.
Review provided by Tripadvisor
Rmdead
Sep 13, 2025
A Lovely Afternoon - What a wonderful afternoon excursion! Captain Luke and Christina were a great team, and knowledgeable and entertaining hosts. They made the trip not only relaxing but enjoyable. Just sit back and enjoy the ride with a drink in hand. I highly recommend Sean's Sangria. And I highly recommend an afternoon sail on the Applejack!
Review provided by Tripadvisor
Adelinet889
Sep 6, 2025
Fantastic & Relaxing Sail on a Historic Schooner run by Women! - The Applejack Schooner was built in about 1940, if my memory is correct. Her captain and 1st mate are very accomplished women who are a lot of fun to sail with and make handling the 4 sails and schooner look easy!! They offered valuable information about the area and delicious beverages for all! Thank you for a lovely afternoon!!
Review provided by Tripadvisor
Julie_m
Aug 28, 2025
Fun day for sailing! - What a beautiful way to spend a few hours! The crew were friendly and made us feel safe. We enjoyed this sailing experience!
Review provided by Viator
Karen_s
Aug 19, 2025
Great Schooner tour of the harbor - Great 2 hours tour of the harbor with Captain Josh and Brian. Highly recommend this to anyone wanting to take a Schooner ride around the Harbour.
Review provided by Viator
Anh_n
Aug 15, 2025
Must-do excursion! - We were able to book a tour the same day. It was a peaceful and relaxing trip. Luke and Katie were excellent crew members who made the experience memorable and enjoyable. Will definitely do this again!
Review provided by Viator
Mariasfromct
Jul 31, 2025
Relaxing trip, beautiful scenery - Our excursion on the Applejack was one of the highlights of our trip to Maine. It was a relaxing ride with beautiful scenery. Captain Luke and Bryan really made it special. Interesting to watch what is involved in sailing.
Review provided by Tripadvisor
Maryanne_s
Aug 28, 2025
Lovely sailing - Beautiful boat, Katie & Bryan were very knowledgeable & personable. Appreciated the small group size.
Review provided by Viator
Pathenderson3
Aug 21, 2025
Scam! - The Captain cancel trip because he had a wedding party. I wasn’t happy, but understood. Still waiting for my refund, now wondering if this was a scam!
Review provided by Tripadvisor
From $55
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).