Continue the leisurely drive south and west through the Keys along U.S. 1, making an obligatory stop at Mrs. Mac’s Kitchen for its famous Key lime pie.
Fishing lovers should pull off in Islamorada to hop aboard the Dirty Boat for half-day to full-day charters. Outdoor enthusiasts can continue 45 miles south to Bahia Honda State Park for fine waterfront cabin camping. Just outside Key West, stop at Stock Island for a delicious hogfish slider at Hogfish Bar & Grill, where outdoor tables sit on the working shrimp docks and bobbing boats fill the view.
In Key West, you’ll find all manner of accommodations, from tiny bed-and-breakfasts to grand waterfront resorts. For a room just a couple of blocks from the southern shoreline — right near the monument marking the southernmost point of the continental U.S. — stay the night at the Best Western Hibiscus Hotel.
The end of the road in Key West is hardly the end of the fun. Go snorkeling at Fort Zachary Taylor State Park. Join the nightly sunset celebration at Mallory Square, an outdoor festival with food and craft vendors, set right along the water near the northern end of Duval Street, the main drag. Tour the Hemingway Home, where the author wrote several of his famous works. Head to Sloppy Joe’s, the famous bar on Duval Street, where Hemingway used to raise a glass.
While Duval Street is full of restaurants and bars, it’s well worth venturing off the beaten path to find a gem of a restaurant to celebrate your drive through paradise. Tucked away on the western end of the island, Santiago’s Bodega serves up tasty tapas like chorizo skewers and yellowfin tuna ceviche in rustic-chic surrounds that Hemingway himself would have loved.