One Hot Night in Key West: Local-Style

First-time visitors to Key West flood the bars on Duval Street, but we chose to seek out the insider spots where island breezes are abundant, seafood is perfectly prepared, Key-lime martinis are authentic and colorful locals will drink with you till dawn.  Here’s our guide to a great night off the beaten track.

 

Take a Sunset Cruise

Feel your worries melt away on the Wind & Wine Cruise as the barefoot captain, with a weathered Panama hat perched on his head, smoothly guides the 65-foot schooner to a front-row seat for the sunset. After hoisting the sails, his ruddy-faced, windblown mates Brian and Sunshine (a perfect name for a Florida sailor, don’t you think?) make the rounds with glasses of wine, gourmet cheeses and crudités. As the open sky transforms into a canvas of oranges, pinks and lavenders blown like crushed chalks, cameras make their way around and everyone shares in an “ahh” moment.

Insider tip:
Feel like trying your hand at the wheel? Just ask. Captain Brian will gladly take a break.
 

Enjoy a Key Lime Pie Martini

After dinner, stroll to Duval Street and turn down Applerouth Lane. This unremarkable side street leads to a lone awning that’s markedVirgilio’s, an upscale martini bar hidden behind La Trattoria Italian Restaurant. A sexy speak-easy vibe prevails here with covered windows and a privacy fence; inside candles are set in iron sconces, while large, gold-rimmed mirrors and retro martini pictures adorn the walls.

Insider tip:
Traditionally, Monday in the Keys is an off night, but Virgilio’s is hopping with $5 Martini Madness.

Party into the Night, Local Style

Many stories of great late nights in Key West finish with “… and we ended up at the Green Parrot”. Only one block from Virgilio’s, this quintessential local dive bar draws all walks of life. Hosting some of the best live blues, funk and rock music, this venue is a great way to finish up the night. Open-air sides are designed for people watching, while the self-serve popcorn and Creature from the Black Lagoon pinball game round out the experience.

Insider tip:The Parrot takes its motto, “No Snivelling,” seriously. If you complain because they don’t serve your favorite drink, you’ll be ignored.

 

Staying the Night

If you don’t have a hotel room when you’re ready to crash, head to the Truman Hotel on Truman Avenue, one block off Duval Street. All the Key West hustle and bustle disappears when you enter the courtyard, where the hypnotic rhythm of the pool’s jets greets you. The hotel has a checkered past, but a recent renovation has transformed the property. Spacious rooms boast tropical orange-and-green décor that’s accented with abstract paintings and zebra-print rugs. When it’s time to sleep, enjoy floor-to-ceiling blackout curtains, a fluffy white bed piled with soft pillows and nighttime chocolates.

Originally published in Florida Travel + Life magazine