The Keys consist of 800 islands strung over 113 miles. How much time you have will determine how close to Cuba you make it. Just an hour and a half from Miami is Key Largo, famous for the 1948 Bogie and Bacall movie of the same name and the breathtaking dive and snorkeling sites at John Pennekamp Coral Reef State Park.

Farther south, Islamorada — which lies less than two hours from Miami — is renowned for its scuba, tarpon fishing and its sunset cruises. For cruises and diving, try Holiday Isle Dive Shop; the folks at Papa Joe's Backcountry Marina can set you up for fishing.

There are countless other pitstops along the way, but if you aim to make the three-hour drive all the way to kitschy Key West, on a quest to retrace Ernest Hemingway's every last bar fight, then an overnight stay is in order. Lay your head at the Marquesa Hotel, a chic boutique inn that provides a restful break from the Margaritaville-types populating the drinking holes on Duval Street.

• 1. John Pennekamp Coral Reef State Park
  102601 Overseas Hwy, Key Largo, FL 33037; 305-451-1202 25.1261153-80.4118681 pennekamppark.com
• 2. Holiday Isle Dive Shop
  84001 Overseas Highway, Key Largo, FL 33037; 1-800-327-7070 x644 25.1243595-80.413686 diveholidayisle.com
• 3. Papa Joe's Backcountry Marina
  Milepost 79.9, Islamorada, FL 33060; 877-665-5599 25.1243595-80.413686 papajoesmarina.net
• 4. Marquesa Hotel
  600 Fleming Street, Key West, FL 33040; 305-292-1919 24.556699-81.801327 marquesa.com