If you think Key West is too hedonistic for families, think again. This compact city with its laid-back, barefoot attitude is the perfect place to bring the kids where they will be allowed to be, well, kids.
What to Do
Hit the beach. Keys beaches can feel a bit limited when compared to the Caribbean's wide stretches of sand, but a pail and a shovel, or a boogie board, are enough to keep any kid happy for hours. For gear rentals and food trucks, head to Smather's Beach. If you want to experience a bit of history and look at coral and other cool flotsam that has washed ashore, Fort Zachary Taylor is just the thing. It also has picnic tables and grills shaded by pine trees, food concessions and bathrooms, so plan to spend the day here and bring your hammock. Higgs Beach—Astro City Playground is a postage-stamp-size beach with a nearby playground. From the playground you're also only three blocks away from the Southernmost Point for the obligatory Key West photo-op.
Visit a remote island. One of the U.S.'s most remote national parks, Dry Tortugas National Park hits all the marks when it comes to cool. First, to get to this park 70 miles off the coast of Key West, you have to take a ferry or, even better, a seaplane. Second, there is Fort Jefferson to explore, which includes cannons, a lighthouse, a moat, and 2,000 archways and five spiral staircases perfect for an epic game of hide-and-seek. Third, from the pristine beach you can snorkel among tropical fish that gather along pilings and the outside of the moat. Tip: If your family is prone to motion sickness, dole out the Dramamine for Kids half an hour before boarding the ferry.
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Bike the Heritage Trail. The Florida Keys Overseas Heritage Trail is a flat bike path that extends over 70 miles. In Key West, a short stretch of it hugs beautiful Smather's Beach along A1A and beyond with gorgeous views of the Atlantic. Another kid-friendly spot is directly across A1A from the bike path: the Fort East Martello Museum, where tykes can climb to the top of the citadel tower, check out shipwreck exhibits, and look at “junk art” sculptures.
Watch the sunset at Mallory Square. Head down to Mallory Square for nightly street theater performances that begin at 5 pm and end when the sun sinks into the ocean. Where else can you see a slack rope walker juggle knives or a unicyclist ride around with lit torches? Some performances are more kid friendly than others, so just keep moving if you hear jokes geared to adults.
Learn about the Keys' Ecology. If a passing shower dampens the beach vibe at Fort Zachary Taylor, pop into the Eco Discovery Center, where everyone can learn about the unique Keys habitats. There are interactive exhibits and tropical fish in a 2,500-gallon tank.
Check out the aquarium. Touch tanks where you can see a live conch; shark and stingray feedings; and rehabilitated sea turtles up the typical aquarium ante at the Key West Aquarium.
Flit with the Butterflies. The Key West Butterfly & Nature Conservancy is a great place to escape the heat or the rain as it's totally glass enclosed, air conditioned, and beautifully landscaped. The whole family will need to be careful where they step and remain relatively quiet, but everyone will be filled with wonder while being surrounded by butterflies.
Have a fun history lesson. Between pirates, ghosts, shipwrecks, and hurricanes, history is anything but boring in Key West. Learn all about it at the Key West Museum of Art & History in the Custom House.
Parents Need a Vacation Too
Find your Zen. Parents can give each other a break from the kids and hit the lovely spas of Key West. If you only have an hour or two free, opt for an in-town spa like Ocean Wellness Spa & Salon. Or you and the family can make a day of heading to Sunset Key, just a 10-minute ferry ride away, to enjoy the sandy beach at the Sunset Key Cottages while you get a treatment at the Spa at Sunset Key. Beach passes are available at the concierge desk starting at 8 am (passes are limited). The $40 per person per day pass includes a towel, chair, umbrella, and the ferry ride to and from Key West. Children under 4 are free.
Yoga on the beach. For early-rising families, park the kids on the sand (supervised, of course), while you do Yoga on the Beach under the shade of pine trees at Fort Zachary Taylor. Classes are available every morning at 8:15 am.
Sip a sundowner. Who says you can't enjoy a drink with the rest of the adult revelers? The line between bar and restaurant in Key West is a bit blurry. Many are open-air, have live music, and serve food, like the Sunset Pier at the Ocean Key Resort & Spa. Key West is one of the few places where you don't have to miss out on live music because the kids should be in bed by the time the party starts. So sip a sundowner while your kids have an early dinner and everyone enjoys the party atmosphere.
Fly directly in and out of Key West International Airport (EYW). There's no gangway, so you'll have the decidedly old-school experience of walking off the plane via stairs. What you might save in airfare flying into Miami or Ft. Lauderdale you will end up spending on a car rental that will be a burden once you reach Key West. Not to mention you'll save yourself the four-hour road trip from Miami, on one-lane U.S. 1, in traffic.
Rent bikes, not a car. Key West is chock-a-block with bike rental companies that will bring bikes to your hotel and pick them up at the end of your stay and include everything from kids' seats to helmets. You are allowed to bike on the sidewalk everywhere in Key West except Duval Street, so kids can stay safe off the street.
Where to Eat
Two food groups are ubiquitous in The Conch Republic and must be sampled: fried seafood (including conch fritters) and Key lime pie. Many restaurants in Key West are outdoor-only or have plentiful outdoor seating—meaning kids don't have to sit still, they often have fun surroundings to explore, and the kids' noise is drowned out by live music, raucous adults, and the crowing of resident roosters. Cats, too, are known to wander through outdoor eateries, even at cloth-napkin spots.
The wait for a table at Blue Heaven can be long at breakfast, lunch, or dinner, but there's a ping-pong table and sometimes a live band to keep everyone entertained.
Take the awesome fish sandwiches and conch fritters with house-made cocktail sauce to go from B.O.'s Fishwagon, or eat at a picnic table at this quirky outdoor restaurant and bar. The ramshackle establishment with a broken-down truck out front has an only-in-Key West feel.
Essentially a food truck with tables and an indoor bar, Garbo's Grill makes for a great lunch stop. It was featured on Diners, Drive-Ins, & Dives, so the secret of their Umami burger and Korean BBQ tacos is definitely out, but head here early and you won't have to wait too long for gourmet-meets-grunge.
Conch Republic has a marina-side location that can't be beat, and there's live music every day.
The perfect spot to hit after sunset at Mallory Square, El Meson de Pepe offers al fresco dining and live Cuban music. A Cuban tapas menu also helps feed picky eaters. Ask for a table near the band or in the pretty courtyard.
For dessert or really any time, Kermit's Key West Lime Shoppe is a must for Key lime pie, or better yet, frozen Key lime pie dipped in chocolate.
Where to Stay
The rule of staying somewhere with a pool to keep the kids happy applies in Key West as anywhere. But don't limit yourself to resorts, because many smaller properties have pools too. If you are visiting in the winter, you'll want to be sure the hotel pool is heated as winter days can still be cool this far south.
The Ambrosia Key West can accommodate larger family groups in cabanas and they have two small heated pools; the dip pool is perfect for toddlers. There's also a hot tub for adults. This is a great option for families who prefer a more intimate feel.
For families on a budget, Authors Key West fits the bill. They have rooms that sleep three (in one queen bed and one twin bed) for only $220 in high season. While being conveniently located close to the action in Old Town, they are specifically not a property for spring breakers, and guests under 16 stay free—plus there's a small pool.
The Casa Marina, A Waldorf-Astoria Resort is on the largest private beach in Key West with a dock to help you get past the rocks on the shore and to a sandy bottom. It also has a babysitting service.
Located on Sunset Key, a 10-minute ferry ride from Key West proper, the one- to four-bedroom cottages at the Sunset Key Cottages have kitchens, and there is a private beach and pool.