Charter the Caribbean founder Dennis Dori took up sailing in earnest at the ripe old age of 39, after he was forced into early retirement from his job as a professional race car driver for being “too old”. He got the hang of sailing and captaining, eventually earning his 100 gross ton U.S. Coast Guard Master’s License.

Dennis operated a small charter sailing company in Chicago in the 1990s. He took corporate and private parties out on Lake Michigan, and also offered themed cruises, sailing lessons, and bareboat rentals for experienced sailors.

The sailing season is short in Chicago, so Dennis decided to expand his business to the Caribbean. In 1992, he opened a charter yacht brokerage firm for clients who wanted to sail in the Virgin Islands and surrounding areas. Fun fact: he was one of the first brokers to promote his services on the Internet.

After a brief fling with retirement, Dennis returned to the brokerage business in 2018 with the launch of Charter the Caribbean.

Dennis is exceptional at helping clients arrange customized sailing vacations aboard fully crewed private luxury yachts based in the Caribbean, Bahamas, South Florida and New England. With thousands of yachts at his fingertips, it’s Dennis’s goal to find the boat and crew that best match your desired location, time frame, and budget.

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