Itineraries for Your Trip to Key West
2 Days in Key West for First Timers
I dream of lazy afternoons in Key West, Florida, indulging in a tangy slice of key lime pie and watching the street performers on Duval Street and in Mallory Square during the nightly sunset celebrations which start two hours before dusk. Sunset, in fact, is my favorite time of day on this inviting island, mainly because you can enjoy the sky’s wild colors from lots of different vantage points—either from land or from the water on a sunset cruise.
While a couple of days in Key West isn’t nearly long enough to really adapt to island time, it’s definitely enough to get a taste of this sunny paradise. Here’s what to do with just two days in Key West.
Weather tip: Key West can get very hot, so wear light, loose, and breathable clothing—and don’t forget a bathing suit.
Key West can get very hot, so wear light, loose, and breathable clothing—and don’t forget a bathing suit.
If you only have time for one thing, make it Fort Zachary Taylor State Park to enjoy historic attractions and sprawling beaches.
Spend your first morning walking or biking through the Spanish Colonial Key West Historic District, a colorful area known for its 19th-century Bahamian conch homes and cigar cottages. There, be sure to stop at local highlights, such as the Ernest Hemingway Home and Museum, the Key West Butterfly and Nature Conservatory, and the Harry S. Truman Little White House, often called the winter White House.
Make your way down to Pier B on foot or by trolley tour to catch a quick catamaran cruise this afternoon—this is the best way to spot whales and sharks, as well as sea turtles, stingrays, fish, and endemic bird species. Many cruises even include polarized sunglasses, which can help you better spot wildlife in the bright, reflective sunlight.
It’s no secret that while Key West is a very family-friendly destination, it also has an active culinary and nightlife scene. This evening, go bar-hopping to sample some craft cocktails—an ice-cold drink never goes amiss, even on the balmiest of Florida evenings. Alternatively, let a friendly and knowledgeable guide take you around to all the best bars in town on a cocktail crawl.
Head out early this morning and beeline for the calm waters of Key West’s mangroves before it gets too hot. These serene marshes are perfect for kayaking or canoeing, and you’ll also learn about the local flora and fauna—think: turtles, fish, and birds—that live in this special landscape. (Just remember that mosquito repellent is a must.)
Explore Key West’s gastronomic side this afternoon and sample Cuban cuisine, key lime pie, fresh seafood, and rum as you visit some of the island’s best eateries. Although you can stop at any spot that looks good—or even take a cooking class, then reserve a table at a fancier restaurant—a good old Key West food tour and cultural walk means you’ll get to see more top foodie favorites with ease.
On your final night, snap a few photos at the Southernmost Point of the Continental USA—you’ll want to remember that you were just 90 miles (144 kilometers) from Cuba—before boarding a sunset cruise. These cruises are among the best ways to get panoramic sea views and say goodbye to this beautiful island in style. Plus, most offer drinks and snacks, while others provide live music.
