The southernmost tip of the United States is often called a sun worshiper’s paradise, and for good reason. Bright rays of light have a particular way of glistening on the translucent teal waters surrounding Key West that beg you to linger as long as you can. The island is also known for its laid-back, eccentric culture that’s sure to have you fully in the moment and embracing the fun you’ll find on its coasts and streets. If you’re into bars, there’s plenty to be found on Duval Street, but if that’s not your scene, no problem. The town is just big enough that there’s plenty to do while still being easy to get from point A to point B any time of day. Here we’ve listed out our favorite ways to spend a laid-back few days on Key West with adults or families.
When should I visit? Winter is the most popular time of year to travel to Key West as daily highs stay in the 70s, a pleasant contrast to most anywhere farther north, and spring and fall are also warm weather wise, though fall is hurricane season. Summer is the hottest season, of course, but if you like the heat, it might be for you.
How to get there? You can fly directly into Key West International Airport or take a scenic drive down through the Florida Keys from Miami, which takes under four hours with no stops. You can also arrive on the island via boat, including a ferry service from Fort Myers Beach or Marco Island.
And now for our top eight things to do while in Key West for a laid-back island vacation.
Choose a hotel with R&R in mind.
While there’s plenty to explore in Key West (more on that below), start your planning by making a reservation at a hotel or resort that creates plenty of opportunities for rest and relaxation during your visit.
We recommend Ocean Key Resort & Spa, which is uniquely situated at Zero Duval Street so you’re a quick walk from shops, restaurants, and the historic architectural charm of Old Town and also have picturesque views of the idyllic teal waters of the harbor side of the island.
Each of the hotel’s 100 rooms and suites (a boutique suite is pictured above) has recently been updated with delightful décor in vibrant colors (including a hand-painted armoire) that capture the energy of the island in a serene retreat of a home-away-from-home. There you’ll find everything you need for downtime including a well-stocked snack and drink bar and a yoga mat to use during your stay. It all complements the hotel’s newly redesigned lobby with elegant tropical floral prints in wallpapers and pillows as well as a new bar and lounge that extends outside with its harbor vistas and ocean breezes.
Watch the sunset.
The nightly sunset with its stunning colors is a must-see event in Key West that comes with plenty of fanfare. Be sure to check the sunset time for the nights you are there and make sure you’re paying attention just before then because it drops fast at the end.
People from all over the island flock to Mallory Square for its famed sunset celebrations and views, and if you stay at Ocean Key, most hotel room balconies offer private views of the setting sun that are just as good as the square below it. Next door at the aptly named Sunset Pier, colorful tables and stools extend from the base of the hotel overlooking the ocean from both sides, making it an ideal spot to watch the sunset while listening to live music and partaking in drinks and bar food (they serve lunch too).
Explore Old Town.
For a quintessentially Key West experience, walk up and down Duval Street—Key West’s version of Bourbon Street—during the day for a more family-friendly experience. You’ll pass plenty of gift stores, art galleries, and open-air bars and restaurants. Be sure to take in the majestic architecture of St. Paul’s Episcopal Church and the San Carlos Institute along the way.
There’s far more to the historic city center than just Duval Street, including lots of 19th-century architecture and historic homes, so be sure to explore nearby streets too. Look for a gigantic kapok tree in front of the Monroe County Courthouse on Whitehead Street (pictured above), and nearby you’ll find fun shops in Bahama Village, including Bésame Mucho for gift-buying treasures and The Green Pineapple and Float Key West boutiques. Also be sure to check out Judy Blume’s bookstore, Books & Books, housed in a distinctive 1950s building that was originally a Masonic Temple. No matter what street you wander down in Old Town, you’re sure to find quaint homes rife with Key West character too.
Watch out for chickens.
Speaking of wandering around Old Town, you’re sure to see plenty of chickens and roosters, and you’ll hear crows all over the island. These birds are very comfortable with humans and seem to almost pose for pictures as they make their way across and along streets (cue “why did the chicken cross the road?” jokes).
The Funky Chicken Store, where you can find plenty of art, T-shirts, bejeweled figurines, and more celebrating the famed Key West chickens, explained the history of all these funky chickens in a marker: Key West settlers originally brought chickens to the island as a source of food when they moved from the Bahamas, and then Cubans moving to Key West as a part of the cigar industries brought another variety used for cockfighting. But once a highway was opened to Miami and eggs and chicken were easier to buy, many residents released their chickens to roam free, and even more roosters were released when cockfighting was outlawed in the 1970s.
Try Key lime pie wherever you can.
Nothing is more refreshing on a sunny day walking around Key West than the tart sweetness in a slice of its famed dessert, the Key lime pie. We recommend trying at least one slice a day as restaurants around the island all prepare it a little differently, and it truly tastes its best in the Keys. For a treat on Duval Street, order a frozen, chocolate-dipped piece of key lime pie on a stick at Kermit’s Key Lime Shop (or order a classic slice or whole pie).
The Key lime experience doesn’t stop with pies either as you’ll find on Key West. At SpaTerre at Ocean Key, in addition to standard massages and more, you can also indulge in a Key Lime in the Coconut Package with an 80-minute massage, a 25-minute coconut crush scrub, and then a ritual bath while sipping a Key Lime Martini or Key Lime Margarita.
Maximize time on or near the water.
Perhaps Key West’s most stunning feature is the translucent teal waters surrounding it, so make sure you spend as much time around it as you can. To fully experience the waters of the island, book a boat tour (sunset cruise, anyone?) or jet skis to go snorkeling, watch dolphins or ocean wildlife from a glass-bottom boat, and more. You can book those excursions through Fury next to Ocean Key or other outfitters on the island.
Not all water time has to be the active variety either. Be sure to also maximize chill time simply taking in ocean vistas. You can order breakfast on a veranda overlooking the water at the Hot Tin Roof restaurant in Ocean Key—there’s no better way to start the day (see photo above)—and throughout the day you can relax in or around the pool overlooking the harbor and order food and cocktails for lunch or snacking at Liquid Pool Bar & Lounge.
Taste your way through local “conch cuisine.”
Key West’s “conch cuisine” was influenced by both Bahamian and Cuban culinary traditions, so be sure to try authentic conch fritters and chowder and local Cuban food while you’re there.
For a nice dinner out, you can dine on Chef Scott Maurer’s “conch-fusion” style, mixing Florida and Caribbean influences at Ocean Key’s Hot Tin Roof restaurant, named for one of the plays written by former Key West resident Tennessee Williams. A short walk away, Café Marquesa offers a menu of “coastal Southern eloquence” in an intimate dining room in a former corner grocery store, part of Ocean Key’s sister property Marquesa Hotel. Be sure to order the beignets at Marquesa, and a slice of key lime pie too.
For a different dining experience, Key West Cooking Show offers part cooking demonstration (with plenty of humor and local flavor) and part history lesson on local cuisine, all with a full four-course meal served as you watch. Menus vary by day, but we were especially partial to the plantain chips with Cuban chimichurri and the delectable flan (and that they send you with recipe cards to try them at home).
Take in local history and ecology.
Key West is an island full of stories and lore, and some of the best ways to learn them are by touring historic sites.
Most notable is a visit to the home where writer Ernest Hemingway lived in the 1930s. A tour of the house will take you to his personal writing studio where he penned seven of his life works as well as past stunning glass chandeliers his wife Pauline, a former Paris-based fashion editor, collected on her travels in Europe, and you can wander the gardens around the home and look out for its famous six-toed cats, all descendants of Hemingway’s first cat, Snow White. Across the street you can visit Key West Lighthouse & Keeper's Quarters as well.
To explore more historical sites, a breezy way to get around is by renting a bike (or better yet an e-bike that will do most of the work for you). Along the way, stop to see the Harry S. Truman Little White House and the famed Southernmost Point marker (and take a picture with the landmark giant buoy if you want to wait in line). From there you can hug the southern coast of Key West to Clarence S. Higgs Memorial Beach, where you can explore the garden-by-the-sea Key West Garden Club and the Key West African Burial Ground memorial.
While you are on a sightseeing excursion, make a stop at the Key West Butterfly & Nature Conservatory where you can walk through a jungle-like greenhouse as hundreds of butterflies representing 30 species fly around you for an altogether mesmerizing experience—and that’s not even mentioning the exotic tropical plants and 30 species of birds (including a pair of flamingos named Rhett and Scarlett).
