There’s a certain charm about Key West, perhaps foreshadowed by the long stretch of placid, crisp blue water on either side of the Seven Mile Bridge, punctuated by remnants of Henry Flagler’s famed old railway. It’s a drive worth making, though flying overhead directly onto the island isn’t a bad alternative. Scenery aside, the island is a quaint paradise, filled with as many quiet pockets as buzzing main streets throughout Old Town long into the night. A trip to Key West is what you make of it, but our rum-soaked 72-hour itinerary is a good place to start. Read on for our favorite places to stay, dine, and drink around Ernest Hemingway’s cherished stomping grounds.
As far as getting to the two-by-four mile island of Key West, there are several viable options including flying directly into Key West International Airport or to Miami or Fort Lauderdale, where one would rent a car for the scenic drive out (Miami is approximately 165 miles from Key West with Fort Lauderdale being slightly further at 188 miles away). Choose whichever adventure tickles your fancy, and upon arrival, head straight for your home for the next few nights: The Gates Hotel Key West.
Once you’ve checked in, get settled into your nautical-chic digs. Take in the view and then make your way to the dreamy pool (with or without your pawed companion––The Gates Hotel is pet-friendly). You’ll want to spend the afternoon lounging by the water, especially given the steady supply of food truck fare and local rum at your fingertips. The Blind Pig serves regionally-inspired and sourced tapas dishes from 7am to 10pm; Rum Row will be your go-to for all things potable, and the Rodriguez Cigar Lounge and garden is worth checking out too.
Venture off the property this evening via the hotel’s Old Town shuttle for a leisurely dinner at Nine One Five, an elevated bistro helmed by Chef Brendan Orr and known for its signature New Island cuisine. Stay past dinner for a late-night glass of wine upstairs––Point5 is open until midnight.
Sleep in and enjoy a sun-drenched breakfast at the hotel.
Make your way back into town to explore island’s most celebrated Hemingway tribute in the form of a stunning rum distillery, backed by his own family and honoring his illustrious life and writing through a collection of two distinct and dynamic Solera blended rums. Join the 1pm guided tour of Papa’s Pilar distillery for an in-depth look and tasting.
Spend this evening exploring more local fare at either Latitudes on Sunset Key (you’ll need a boat to get there) or Turtle Kraals, a Caribbean seafood joint housed in a former turtle cannery. You can’t go wrong with either choice.
Depart The Gates Hotel, rum in hand, to return to reality.