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About Us

The Pineapple’s Journey

In 1976, the Pineapple (then “Vida Loca”) was launched in Chicago, Illinois and began an epic journey from the Great Lakes, out the Canal, down the Hudson and out to the Atlantic. Then, she traveled down the East Coast to Florida, where she cruised throughout the upper Caribbean and the Keys. Changing hands a few times, she ended up in the panhandle of Florida in the coastal town of Niceville as a liveaboard with an owner who had “never even sailed her.”

We found her in the fall of 2004 in such rough shape that we could not even consider sailing her back to Maine. After a long winter of hard work, the Pineapple was christened with her new name and launched into the chilly Atlantic in the spring of 2005. The Pineapple Ketch sailed as a “six pack” for two seasons while we went through the process of certifying her as a United States Coast Guard Inspected Vessel to accommodate 14 souls.

The Pineapple Ketch has had a wonderful career in Kennebunkport and has been witness to many proposals, weddings, honeymoons, and celebrations along with being seen in countless photos, magazines, newspapers, videos, TV shows, and advertisements.

The Pineapple Ketch has been sailing out of Kennebunkport since 2005. All of our captains and crew members are local folks with extensive knowledge of the coast as well as suggestions for what to do while you are visiting. Our crew carries current CPR and First Aid certifications as well as having all required United States Coast Guard licenses.