Consider the mecca of many a Florida Keys pilgrimage- Key West, the last stop on the line before you’re headed for Cuba about 90 miles away. The place has long drawn legions of colorful characters ranging from Tennessee Williams to Ernest Hemingway. Several presidents also vacationed here; Franklin D. Roosevelt was a particularly big fan.

If heading ashore, many often head to Duval Street. You can even take part in the Duval Crawl, a do-it-yourself bar crawl along Duval Street in the heart of town. (Check often due to Covid restrictions)

Marinas are plentiful on Key West for boats of most sizes: