There’s much more to a weekend in Key West, Florida, than Mallory Square sunsets and Ernest Hemingway look-alikes.

Sitting just 150 miles south of Miami and 90 miles of Havana, Key West’s brightly painted homes and colorful crowd have become its calling card. And while the thriving nightlife is an obvious draw, don’t be surprised to find a number of fine art galleries and yachting pursuits. Whether enjoying an ocean view lunch in earshot of the famed local chickens or taking in street performers who throw flames in the square, you’ll find that the hidden highlights of this island only continue to grow year after year.



Escaping from the hustle and bustle of downtown Key West is as easy as checking into The Laureate Key West. This coastal-chic, all-suite resort, located right on the bay, is the perfect starting point for exploring the vibrant culture of Key West. For the ultimate seclusion, Sunset Key Cottages is located on a 27-acre island seven minutes away by boat from Key West, so you, too, can have a private escape from the city.


Simonton Street’s Better Than Sex restaurant reinforces the southernmost outpost’s free spirit and specializes in one type of food group: sweets. Staples items include Chocolate Grilled Cheese and Kinky Key Lime Pie, as well as drinks like Argentinean wines served in chocolate-rimmed goblets and apple-infused beer in caramel-lined glasses. That’s one way to start a trip.



It may seem a bit morbid, but taking a 90-minute tour of the 20-acre Key West Cemetery with the Key West Historical Society reveals the kooky, for-the-fun-of-it mentality that floats through the sweet, humid air – even in death. Quirky epitaphs include a large white crypt upon which the phrase “I told you I was sick” is inscribed and pink granite gravestones for three Yorkshire terriers and a pet deer named Elfina.


Since it was scuttled in 2009, the 523-foot long USNS General Hoyt S. Vandenberg has become a popular diving site for its plethora of sponges, arrow crabs, and patrolling barracudas. This easily accessible – just seven miles south of Key West – wreck is the second largest artificial reef in the world with plenty of nooks to explore along its bridge, main deck, and giant dish antennas.

Big Fish

Above the surface, all-day fishing excursions with Captain Chris Robinson are more than just baiting tarpon and bonefish. This 20-year local can tell you how he befriended a struggling Jimmy Buffett. Ask him about the night Hunter S. Thompson had a midnight boating mishap, wreaking havoc on a local harbor.


Caffeine Boost

Before heading home, a Cuban to-go is a must – that’s a coffee, anyway. The not-watered-down iced coffee at the Cuban Coffee Queen gives an extra perk to the average Joe. Here, cubes for iced coffee are actually frozen blocks of straight coffee. A morning staple for groggy locals, too, the colorful shack is within walking distance of the water and sports a scenic Key West postcard mural.

Where to Stay The Laureate Key West | Sunset Key CottagesOpal Key Resort & Marina| The Capitana Key West