Planning a two-day trip to Key West?
Follow this guide to get the most out of your time on the island.
Start your morning right with breakfast at one of Key West’s most classic restaurants, Pepe’s Café, founded in 1909. Tucked behind a white wooden fence on Caroline Street, snag a table in the cozy backyard or belly up to the small bar where friendly bartenders squeeze fresh orange and grapefruit juices before your eyes as orders for screwdrivers and greyhounds roll in. This is Key West after all and “it’s five o’clock somewhere” definitely applies! Breakfast specials are the way to go with hearty options ranging from omelets to French toast.
Afterwards, make your way towards Duval Street where you’ll find a slew of restaurants, bars and shops – and plenty of rowdy revelers cruising Key West’s main street. Points of interest include Sloppy Joe’s Bar, Oldest House Museum, the San Carlos Institute and Margaritaville.
Head to the southern stretches of the island where the Atlantic Ocean laps against Key West’s shore. Here is where you’ll find Smathers Beach. There’s a range of activities to choose from including volleyball, Hobie cat rentals and other water sports. You’re also never far from food vendors in case you get hungry. The main attraction, of course, is endless ocean views and the warm sun on your shoulders. Nearby, visit the East Martello Fort, a Civil War era fort that’s home to Robert the Doll, a haunted doll with a creepy story. It’s a fun stop for any ghost story lover.
Head back towards Old Town and discover a quirky piece of Key West history with the Key West Cemetery. Covering 19 acres, the cemetery opened in 1847. There’s plenty to learn from stories told through the tombstones including this irreverent gem: “I told you I was sick,” scrawled on one famous headstone.
Make your way to Mallory Square in time for sunset. You have two options for experiencing the famous spectacle. One, the classic way, is to enjoy it at Mallory Square complete with street performers, magicians and food stands dishing up everything from conch fritters to mojitos. Two, board a state-of-the-art catamaran with Fury Water Adventures on a two-hour sunset sail with all you can drink beer, wine and champagne. The good news is: You can’t go wrong with either option. Opt for dinner after sunset at El Meson de Pepe for delicious Key West Cuban food, located directly in Mallory Square.
Key West is home to the third largest coral reef in the world; so heading seven miles offshore for a snorkel trip is an absolute must do on any Key West vacation. Join Fury Water Adventures for a three hour morning snorkel trip where you’ll sail to the reef and snorkel with incredible marine life, like yellowtail snapper, rainbow parrotfish and maybe even a stingray or sea turtle. On the sail home, it’s all you can drink beer and wine – not to mention, spectacular views.
After your snorkel trip, make your way around the Historic Seaport with yachts, fishing charters and sailboats docked in the marina. It’s a piece of Old Key West with laidback boat bars alongside upscale restaurants. For lunch, opt for the Conch Republic Seafood Company. This open-air bar and restaurant features a giant wraparound bar and ample seating, serving up fresh fish and strong drinks. If you’re lucky, you might even catch a live musician to set the mood.
The Southernmost Point is a must visit on any Key West vacation. Make your way to the southern end of Simonton Street for your photo op by the buoy marking 90 miles to Cuba. While you’re there, swing by the Southernmost House Grand Hotel & Museum. This Victorian-style historic home is an eclectic mix of seafoam green and conch shell pink, making it one of the most beautiful properties in Key West.
Veer off the beaten path and visit Bahama Village for dinner, particularly down Petronia Street towards Santiago’s Bodega. There’s plenty of local color to discover on your walk, from charming shops to casual restaurants. Santiago’s is a longstanding favorite, serving a Spanish tapas-inspired menu with highlights including beef tenderloin with blue cheese butter, seared grouper with fennel and saganaki made with flambéed haloumi cheese.
A Key West vacation itinerary is not complete without hopping aboard the Old Town Trolley. A Key West institution for over 30 years, those venerable green and orange trolleys consistently rank at the top of things to do in Key West. With the single largest fleet in the city, you’ll spend less time waiting and more time sightseeing. Their friendly and knowledgeable conductors will take you on a fully narrated journey filled with humor and history. Explore the must-see sights of the Conch Republic. A really handy, time-saving component built into this tour is the freedom to hop on and hop off at any of the 13 stops they service, allowing you to maximize your 2 day vacation.