Key West is all about fun under the sun—and long after it sets.
Sunset Pier at Ocean Key Resort & Spa in Key West lives up to its name.
Ocean Key Resort
It’s a long drive to Key West, so why not time your arrival to coincide with happy hour? At day’s end, the party’s already started in Mallory Square in anticipation of the Sunset Celebration. Here, street performers, musicians and artists all vie for your attention as the sun appears to set into the Gulf.
If you prefer to observe the spectacle far above the madding crowd, check into the Ocean Key Resort & Spa and request a room overlooking the square. Or, split the difference and get closer to the action while avoiding the sweaty press of people by watching the sunset from the resort’s waterfront Sunset Pier, Liquid Lounge Pool Bar or Hot Tin Roof Restaurant.
This tiny speck of land located less than 100 miles north of Cuba is far more than bars and tacky T-shirt shops. It’s filled with more history, natural beauty and colorful stories per acre than any place this small ought to possess. You’ll find more to see and do than you can fit into a long weekend.
What to Do
Key West Lighthouse
Mallory Square is party central; you can find out about scheduled events, featured artists and even what time the sun will set on a specific date at sunsetcelebration.org. After dark, stroll down Duval Street for drinks at the bounty of bars, including Hog’s Breath Saloon (hogsbreath.com/key-west), Sloppy Joe’s (sloppyjoes.com) and Captain Tony’s Saloon (capttonyssaloon.com), the original Sloppy Joe’s where Ernest Hemingway hung out in the 1930s. Visit the home where the great author briefly lived (hemingwayhome.com; admission $13) and catch a glimpse of the six-toed cats, descendants of Papa’s own feline, who still call the place home. For a bird’s-eye view of the island, climb the 88 steps to the top of the
Key West Lighthouse (kwahs.com/lighthouse; $10). Get a taste of history at the Harry S. Truman Little White House (trumanlittlewhitehouse.com; $16.13), originally the command headquarters when the Spanish-American War began and later a favorite retreat of our 33rd president, or take in some beach time at Fort Zachary Taylor Historic State Park (floridastateparks.org/forttaylor; $2.50 per person). Key West can wear you out, but a visit to Ocean Key’s SpaTerre (oceankey.com) for a massage ($110-$185) will help revive your energy level.
Where to Stay
Ocean Key Resort & Spa guest room
Zero Duval Street may end at the waterfront, but it’s the beginning of a memorable stay in the Keys. Here, the Ocean Key Resort & Spa (oceankey.com) is at the terminus of what’s arguably the most famous paved party route next to Bourbon Street. Ocean Key and its restaurant, Hot Tin Roof, have won a host of awards, including a four-diamond ranking from AAA. Room rates start at $429 a night. Key West is small, and Ocean Key is ideally located, so you can walk just about anywhere. But to get there faster, ask at the front desk about renting a bike (24 hours, $18); it’s the best way to get around the island. The concierge can also arrange for sunset cruises, fishing trips, snorkeling and other activities.
Where to Dine
Kelly’s Caribbean Bar, Grill & Brewery
If you like to mix a little stardust with history, Kelly’s Caribbean Bar, Grill & Brewery (kellyscaribbean.com) is a great spot to sit on the patio and dine on the catch of the day. The simple wooden structure is where Pan American Airlines got it start in 1927, and it’s named for its former owner, actress Kelly McGillis of Top Gun fame. Or stay alfresco but head south of the border at Salsa Loca (305-292-1865). The spicy Mexican dishes are a tasty counterpoint to the frosty alcoholic libations, the ultimate motivation for sitting back and relaxing in Key West.