Day Five: Islamorada to Key West (81 miles)
At the road trip’s end: the southernmost point of the continental United States.
Breakfast: Green Turtle Inn
Revamped 1940’s diner with one of the best morning meals around (just try to resist the coconut French toast). 81219 Overseas Hwy., Islamorada; 305/664-2006; breakfast for two $20.
Do: Robbie’s of Islamorada
Feeding the tarpon ($3 for a bucket of bait) off the dock of this water-sports center is a Keys rite of passage. 77522 Overseas Hwy., Islamorada; 305/664-9814.
Lunch: Seven Mile Grill
Just north of the Seven Mile Bridge, which connects Marathon to the Lower Keys. Order the grouper sandwich. 1240 Overseas Hwy., Marathon; 305/743-4481; lunch for two $25.
Shop: Isle Style
A true fashion oasis in souvenir-laden Key West: colorful women’s wear and accessories that would look equally at home on the beaches of Malibu. 1204 Simonton St., Key West; 305/292-4000.
Stay: Casa Marina, a Waldorf Astoria Resort
Great Value Rita Hayworth and Gregory Peck are among the stars who once stayed at this revamped 1920 compound, another product of Henry Flagler’s bold vision. Doubles from $199.
See: Key West Sunset
The main event in town. You could brave the carnival-like Mallory Square, where the rowdy Sunset Celebration involves sword swallowers and fortune-tellers. Or you could sit back with a cocktail at Casa Marina’s Sun Sun beach bar and toast the day’s end in a more civilized fashion.
Dinner: Pepe’s Café
Atmospheric little shack that’s the oldest restaurant (est. 1909) in Key West. Head here primarily for the Key lime pie—pleasingly tart, garnished with whipped cream, and served in a bowl. 806 Caroline St., Key West; 305/294-7192; pie for two $8.