A perfect day in Key West


What Key West lacks in size (it’s roughly four miles long and less than two miles wide) this little island makes up for in character: fresh seafood, breathtaking sunsets, and waterfront dive bars. A single day in the Conch Republic is hardly enough time to experience everything this oddball community has to offer, but this itinerary showcases the charm and grit that’s come to define the southernmost town in the continental United States.
Key West is a study in contrasts and this itinerary mixes the can’t-miss landmarks with quiet respites in nature, literary history with the island’s famous tangy dessert, and upscale elegant eats with down-home dive bars. We’ve also incorporated real Tripadvisor reviews and ratings of what other travelers have learned and loved so you can make the most of your trip, too.
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MORNING: An iconic photo and communing with nature



A large part of Key West’s appeal is it’s geography: It is the last island on an archipelago that stretches 125 miles off the tip of Florida and only 90 miles from Cuba. A 12-foot-tall red, blue, and yellow buoy at the Southernmost Point conveniently lists these attributes, which makes taking a photo beside it highly sought-after. Set the alarm before 8 a.m. to arrive long before the sun starts searing down and the queue for photos winds down the block.
Once you’ve snagged the coveted photo, head east towards Indigenous Park, a seven-acre native tree and bird park with shaded footpaths winding through some of the oldest trees on the island and rescued pelicans, owls, cormorants, and ibises at the Key West Wildlife Center that’s also located on the grounds.
Just across the street is the West Martello Tower, a red-brick fort built in the 19th century that has since been refashioned into a lush, blossoming botanical garden. The best seat in the house is a white gazebo that overlooks the turquoise waves crashing onto Higgs Beach.
Travelers say: “This is just a marker at the Southernmost Point of the continental US and is 90 miles from Cuba. Go early as the line gets long in the afternoon. We were here on a cruise stop and walked there first thing off the ship and only waited about a minute. People in line are great about taking your picture and you take theirs. It was fun to get the picture.” —NorCal-traveler08
AFTERNOON: Key West eats and literary history

Now that you’ve hit your daily step goal, it’s time for lunch. Head to the corner of Thomas and Petronia Streets in Old Town, where crowing roosters announce your arrival at Blue Heaven, a no-frills dirt yard with individually painted tables and mismatched plates that boasts shrimp and grits, fresh fish sandwiches, and light bites. Whatever you do don’t skip dessert: a slice of their famous key lime pie made with a buttery cracker crust, freshly squeezed lime juice, sweet condensed milk, and heaps of meringue.
On the next block, you’ll find The Ernest Hemingway Home and Museum, a Spanish Colonial mansion where the storied author lived in the 1930s and wrote Death in the Afternoon, The Green Hills of Africa, and To Have and Have Not, and short plays including “The Snows of Kilimanjaro.” The guided tours are frequent and educational, but be sure to take in the view of the Key West Lighthouse from the second-floor veranda and the adorable colony of lazy six-toed cats who appear to run the place.
For anyone seeking to cross paths with a living literary hero, head on over to Books & Books, a nonprofit bookstore co-founded by Are You There God? It’s Me Margaret author Judy Blume, who sometimes can be found manning the cashier herself.
Looking for a quiet oasis to kick up your feet? Look no further than The Gardens Hotel, a 20-room boutique inn dating back to the 1800s with crown molding, brocade curtains, and a surprisingly high-tech self-serve wine bar. Press the button to fill your glass and step outside to a shaded nook among the rare orchids, black bamboo, and koi pond in the namesake garden.
EVENING: Pastel sunsets and seedy dive bars

Figure out when the sun will set and, roughly an hour before, join the throng of oddball locals and wide-eyed visitors to Mallory Square for a communal waterfront viewing of the sunset. There’s plenty of kiosks selling knickknacks and souvenirs and curious street performers on stilts and tightropes all vying for your attention, but the setting sun is the true star of the show.
Dinner tends to be a far more serious affair and might be worth considering a quick outfit upgrade from shorts and sandals. Antonia’s, which is one of the most popular restaurants in town, is an elegant Italian option with a carb-lover’s offering of pastas.
For the quintessential Key West experience, simply stroll down Duval Street to witness the drunken shenanigans. For anyone looking to partake in the revelry themselves, consider any of the seedy dive bars within a half-mile radius: Capt. Tony’s Saloon, a dimly lit bar festooned with dollar bills and brassieres that Hemingway was rumored to have frequented; Green Parrot Bar, a classic Key West bar where a small plaque near the bathrooms states that “Elvis Presley Slapped Hemingway Here” in 1957; and The Chart Room Bar, a laidback watering hole that doles out free popcorn with cocktails and is tucked inside the Pier House Resort & Spa.
GETTING OUT ON THE WATER TOUR OPTIONS
- Key West’s sunsets are legendary, and the snazziest way to experience it is on a locally owned sailboat with complimentary wine.
- There’s arguably no one better than Captain Sheri, founder/director of the Florida Keys Wild Dolphin Alliance, to take you out on the water to learn about and encounter wild bottlenose dolphins.
- For a slower pace, consider an eco kayak tour that’ll wind through the backcountry mangrove channels and get you up close to natural wildlife.
Worthy detours along the way
Know Before You Go
Key West is most comfortable weather-wise between November and March, when the temperatures and humidity are at their lowest. But for anyone looking to snag a hotel deal, consider visiting during the summer — just pack plenty of sunscreen and an umbrella.
Everyday is a good day to visit Key West. Most eateries, establishments, and attractions are open seven days a week. Weekends tend to be more crowded so consider a midweek visit for a more laidback vibe (and an easier time finding parking).
Most museums and attractions close around 5 or 6 p.m. Restaurants typically stop serving around 10 or 11 p.m. (though there are plenty of late-night spots, especially on Duval Street). Since last call isn’t until 4 a.m., most bars and lounges stay open late.
Old Town: For those looking to stay close to the raucous action, Old Town is for you. Everything’s within walking distance, and most accommodations have fascinating histories and date back to the 19th century. Consider the Key West Historic Inns Collection, which includes five historic properties across Old Town that feature three private pools, an outdoor bar, and a tropical white and wood-toned palette.
New Town: On the quieter side of the island, New Town is a whole lot easier to navigate, find parking, and, like the name suggests, features newer construction. With a lagoon pool and classic midcentury cars, Havana Cabana is a 106-room hotel overlooking the bay on Roosevelt Boulevard and inspired by the island nation 90 miles away.
Stock Island: Though it’s not technically on Key West, Stock Island is just across the Cow Key Channel on the neighboring island. It’s grittier on this side of the channel with marinas, fishing boats, and colorful mobile homes. But The Perry Hotel & Marina embraces the seafront charm with its sleek design that incorporates concrete, steel, and wood. Rooms overlook the pool and boats bobbing dockside at the 229-slip marina.
Public transportation: There’s no metro or subway system here, but public buses do service the island, connecting Stock Island, New Town, and Old Town. The Duval Loop is a free hop-on, hop-off service that makes 18 stops across Old Town, where parking is notoriously difficult.
By hotel shuttle: If you’re staying at a hotel in New Town or Stock Island, check with the front desk since most hotels offer regular shuttles to and from Old Town.
By bike: Key West is certainly more bike-friendly than it is car-friendly. There’s plenty of bike racks posted around the island and no shortage of bike tours to choose from.
By rideshare: Uber and Lyft service the island.
By taxi: Cabs service the island as well. Though you’ll most likely find them posted near the airport.