$20 for Two-Hour Sail Aboard a Schooner (Up to $37.50 Value)


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$37 46% $17
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In a Nutshell

  • Two-hour trip
  • 90-foot, nicely rigged schooner
  • Sail through the oldest working seaport in America

The Fine Print

Promotional value expires Oct 11, 2010. Amount paid never expires. Limit 4 per person. Season starts 5/8, weather permitting. Subject to cancellation due to weather. Not valid for feature trips. 24-hour cancellation policy or Groupon is forfeited. Reservation required. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Pirates will always sail aboard schooners since there is plenty of cargo space to stash tiny hats for their parrots, and painting a skull and crossbones on two masts rather than one is twice as intimidating. Set sail for reveling rather than pillaging with today's Groupon. For $20, you get a two-hour sail (up to a $37.50 value for adults) aboard the Thomas E. Lannon, a schooner that makes its home on Rogers Street in Gloucester.

So what is a schooner? A schooner looks like one of those miniature ships that are trapped in bottles; they have two or more masts and a ton of sails. The Thomas E. Lannon is a 90-foot vessel, crafted with incredible intricacy and manned and owned by a nice-looking family. The Lannon can carry up to 49 people on each of its four daily sails around Gloucester, the oldest working seaport in America. On your two-hour trip, you can relax and enjoy the view, or you and your guests can help raise the sails. Take a virtual tour of the ship to see what it's like.

The Lannon sails until mid-October this year (when this Groupon expires), so don't miss out; spending an afternoon out on the water in a one-of-a-kind ship impresses the whole family and makes seagulls jealous.


There isn't a lot out there about the Thomas E. Lannon, but what is there is glowing. Seven Reviewers on Yahoo!Travel give the Lannon experience five stars:

  • I loved everything about my sail on this beautiful schooner. I would recommend it highly to anyone who loves the sea. The owner and his sons were very professional and friendly and gracious. – Rick Pawlenty
  • Can't remember having a better day. It was filled with wonder and laughter and the wind and full sails were breathtaking. Took the tiller and didn't hit anything, a first for me. – A Yahoo! Contributor
  • Absoultely [sic] a great schooner, went sailing las [sic] June and will be back this year to join in on the Schooner races. Tom and Kay were fantastic, and we really had a wonderful time. Thumbs up to the Lannon and her crew! – Christine

Thomas E. Lannon

While the Thomas E. Lannon schooner boasts many impressive characteristics—including a 65-foot deck and a resemblance to a 1903 sword-fishing schooner—none of them rivals the story of how the vessel got its name.

Before the ship was built in 1997, founder Tom Ellis was visiting his relatives in Newfoundland when he overheard them reciting stories of his grandfather Thomas Lannon, who had fished the Gloucester coastline for more than 40 years. On one particularly stormy day in 1908, Lannon and five other men set out into the waters off Nauset aboard two dories and rescued the crew of the capsized schooner Eric amid 70-mph winds. Each of the rescuers received the eternal admiration of the rescued men and a medal from the Massachusetts Humane Society, which Ellis possesses to this day.

More than a century later, the crew of the Thomas E. Lannon keeps its namesake's love of the sea alive by chartering an array of sailing voyages that have attracted more than 100,000 passengers to date. After helping raise the sails at the voyage’s start, passengers capture vivid views of Gloucester harbor's lighthouses, castles, and beaches.

Customer Reviews

Lovely way to experience Gloucester Harbor! The crew is wonderful and really great with kids.
Catherine C. · August 11, 2014
A great way to get out on the water for a short period of time relaxing under the sun. Dont forget to bring a jacket even on a nice day!
Michelle P. · June 22, 2014
The captain was informative, friendly, and funny; the boat was beautiful as was Gloucester and my friend and I had a lovely day.
Catherine H. · December 12, 2016
Merchant replied
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Glad you had a good time aboard our vessel
Merchant replied · March 23, 2017

By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.