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Address: Pier 1, Boothbay Harbor, ME
Phone Number:
+1 207-975-2628
09:00 - 19:00
Open now
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Sun - Sat 09:00 - 19:00

Lazy Jack takes her lines from the traditional Gloucester fishing schooners...

Lazy Jack takes her lines from the traditional Gloucester fishing schooners of the 1850's and has had a colorful and notorious history as a fishing and passenger charter schooner. During the early years Lazy Jack sailed between the East Coast, Man O War Key and Cuba running guns, rum, cigars and bananas. Today Lazy Jack offers 2 hr. day sails or private charters from Pier 1 in Boothbay Harbor celebrating 66 years of continuous sailing and 10 years as Boothbay Harbors only historic working schooner. Lazy Jack is owner operated by Captain Joe Tassi and his son Michael.

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TripAdvisor Reviewer Highlights

Read all 128 reviews
Visitor rating
  • 103
  • 13
    Very good
  • 4
  • 3
  • 5
Nice 2 hour sailing adventure!

We embarked on an early morning trip. It was misty and a slight drizzle. Captain Joe and Mike put you at ease with pleasant conversation and the gentle wind propels you out... read more

5 of 5 bubblesReviewed 11 July 2013
John L
Bloomsburg, Pennsylvania
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128 Reviews from our TripAdvisor Community

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Showing 128: English reviews
Bloomsburg, Pennsylvania
1 review
5 of 5 bubbles Reviewed 11 July 2013

We embarked on an early morning trip. It was misty and a slight drizzle. Captain Joe and Mike put you at ease with pleasant conversation and the gentle wind propels you out through the bay. Plenty of sights to see, a really laid back adventure. It was cool and sunny by the time we got back. I would recommend this... More 

Thank John L
Binghamton, New York, United States
Level Contributor
3 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 8 July 2013

We make a trip on the Lazy Jack one of our annual "Must Do's" when visiting the Coast of Maine. Booking is easy, they are always on time, and Capt Joe & Mike always treat us to a calm wind and cool conversation. This boat is family friendly, and we highly recommend to anyone looking to see Boothbay the way... More 

Thank Jen O
Bath, Maine
Level Contributor
3 reviews
5 of 5 bubbles Reviewed 1 July 2013

We had a wonderful day and chartered the whole boat for the birthday celebration.....four generations on board.....a terrific sail...so gentle the 90 and a 92 year old on board were "happy as clams!" Joe, the captain, was knowledgable, an expert sailor, not at all intrusive but happy to answer all of our many questions. The weather broke, the sun came... More 

Thank lawr_k
Little Rock, Arkansas
2 reviews
5 of 5 bubbles Reviewed 30 June 2013

On our return trip to Boothbay Harbor this year, we decided to go on an afternoon sail on the Schooner Lazy Jack. So much fun! According to Captain Joe the weather hadn't been cooperating much, but we lucked out and had a fantastic sail with a bit of sun and fair amount of wind. Would highly recommend this tour to... More 

Thank Sam S
Fort Worth, Texas, United States
Level Contributor
10 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 12 helpful votes
5 of 5 bubbles Reviewed 30 October 2012

OMG! Just the best sail ever in all our times on the water in Maine! On a cold, drizzly, overcast morning the day after Columbus Day, a strong, prevailing easterly wind was blowing. Being sailors ourselves, we wanted to get out on the water, but many of the boats were done for the season. Captain Jack took my husband and... More 

Thank Emie S
coppell texas usa
Level Contributor
100 reviews
62 attraction reviews
common_n_attraction_reviews_1bd8 26 helpful votes
5 of 5 bubbles Reviewed 30 September 2012

My Daughter and I thoroughly enjoyed our sunset cruise on the Lazy Jack. There were only 5 total guests on the boat, with great weather. The Sunset was amazing!! Very relaxing with a glass of wine and the cool wind in the sails!

Thank barbaradtaylor
Richmond, Virginia
Level Contributor
8 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 28 September 2012

Had a wonderful time with Joe and his son Michael on the Lazy Jack! My wife and I appreciated that this wasn't the typical narrated tour that you find on the big harbor cruises with tourists packed shoulder to shoulder. Captain Joe was friendly and answered questions as we had them, but really lets you enjoy the scenery and the... More 

Thank Chris U
2 reviews
5 of 5 bubbles Reviewed 24 September 2012

My wife and I finally made it to our annual Boothbay Harbor vacation last week. Looking for something to do that afternoon we were advised by our B&B owners of cruises on the Lazy Jack. We scheduled a sunset cruise that evening. The weather and sights couldn't have been any better, saw Loons, a seal and cormorants. Enjoyed talking with... More 

Thank J C
Houston, Texas
Level Contributor
56 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 33 helpful votes
5 of 5 bubbles Reviewed 18 September 2012

Signed up with the Lazy Jack last Friday for the 5 o'clock sail. I loved this experience. It was so peaceful and relaxing. I felt fortunate that there were only 5 of us passengers and then Joe and Michael. I'm not much of a people person but this felt like a trip with friends. Engaging conversation with the captain... there... More 

Thank TakeAPicture-PaintIt
Leominster, Massachusetts
Level Contributor
72 reviews
31 attraction reviews
common_n_attraction_reviews_1bd8 23 helpful votes
5 of 5 bubbles Reviewed 17 September 2012

My wife, daughter and I had a great time on this excursion. We really liked the fact that we were actually sailing, and that a peaceful day on the water wasn't interrupted by lots of chatter. We did enjoy chatting with the crew, and learning about the history of the ship and the Captains interesting background. We also enjoyed laying... More 

Thank pghtransplant

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Questions & Answers

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4 questions
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6 months ago
East Moriches, New York
6 months ago
Gorham, Maine

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?