The Florida Keys: Islamorada to Key West (70 miles)
For me, every road trip to Key West truly begins with the road itself, U.S. Highway 1, a fabled trail that winds its way from Fort Kent, Maine, to Key West, mile-marker 0. In Islamorada, the Moorings Village & Spa ($$$) is the uptown end of Keys retreats and, better yet, provides convenient access to M.E.A.T. ($), a new smokehouse and taproom featuring an enormous elk head mounted on the wall. Not that long ago, the Keys were all fried fish, generic beer, and steel-drum bands churning out “Yellow Bird.” True to its name, M.E.A.T. serves everything from house-made bacon to duck-fat-fried french fries, accompanied by craft Florida beers like Monk in the Trunk Organic Amber Ale.
In the early 1900’s, the islands of the Florida Keys were linked together by Henry Morrison Flagler, who brought his Florida East Coast Railroad south with the now-gone Over-Sea Railway. At mile-marker 47, more than 400 workers for the original Seven Mile Bridge lived on Pigeon Key, which remains the prettiest—and perhaps the most upstanding—attraction in the Keys.
At mile-marker 28.5, off Little Torch Key, I take the motor yacht shuttle to the classic Little Palm Island Resort & Spa ($$$$) for a nicely calibrated lunch of grilled snapper and—of course—Key lime pie. It’s worth the effort: tiny, endangered Key deer, which live only in the Florida Keys, swim over from an adjacent island, milling among the outdoor dining tables like skittish exotic pets.
In Key West I check in at Cypress House Hotel ($), then immediately leave to breathe in some local atmosphere. West Martello Tower, an eccentric garden in a Civil War oceanfront fort, never fails. Ditto the antiques shopping at Duck & Dolphin Antiques (601 Fleming St.), with finds including a Regency-era secretary once owned by the Duchess of Kent.
Brunch is a big deal in Key West, a town dedicated to stretching out life’s little indulgences. On Sundays, it runs until 3 p.m. (no surprise) at the restaurant 2 Cents ($$$), half a block from Duval Street on Appelrouth Lane. The bartenders work major looks (1950’s glamour-gal dresses accented with Bettie Page stylistic conceits) and dance to rocker-girl hits like Nena’s “99 Luftballons.” An order of truffle fries is essential.