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)

• Sloppy Joe’s Bar, has been around forever (the 1930s) and starts pouring drinks by 9 a.m. most days and then hosts live music many nights.
• The Bull and Whistle Bar is another favorite and its filled with murals that tell the story of the city.
• Of course, any visitors to Key West will want to have their photo taken at the giant “buoy” on land that marks the Southernmost Point in the continental United States.
• History minded buffs will enjoy Then, head over to the Ernest Hemingway Home and Museum, where the writer lived during the 1930s on Whitehead Street across from the lighthouse.
• The Hemingway property has been a museum since the 1960s (officials say this property is a more popular tourist attraction than the Duval Street bars, even). 

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