#1: History Like No Other Place

Key West’s history reads more like an epic movie. From an indigenous boneyard to a secret haven for pirates to a military outpost, Key West has been home to shipwreck salvagers and bootleggers, playwrights and politicians and everyone in between. Geographically it’s closer to Cuba than Miami and you’ll see all of this reflected in the architecture and arts. When roaming the streets of Key West, you’ll exhaust yourself trying to photograph all the historic markers. Visit keywesthistoricalmarkertour.org and download a free app that narrates a walking tour for you.

#2 Famous Felines

The Ernest Hemingway Home & Museum is not only a sweet oasis from the busy streets, it also features the descendants of Hemingway’s own famous six-toed cats. These cats have the run of the place and are as mellow as they come. You can pet them (but no picking them up). If the kids are little, skip the guided tour and explore the property and historic home on your own. Look for paw prints in the cement! 

#3 Maritime Marauders

The Mel Fischer Maritime Museum tells the story of this world-famous treasure hunter and includes many of the spoils he salvaged from the wreck of the Atocha. Upstairs you’ll find pirate history and a few interactive exhibits for the kids.The Shipwreck Museum offers plenty of interactive fun for the kids but the real highlight is the view from the top of the tower. The Key West Lighthouse & Keepers Quarters  lis right across the street from the Hemingway Home. Kids 6 and under are free and you can climb the 88 steps to the top of the lighthouse.

#4 Kid-Friendly Cuisine

The rich culture of Key West, from Cuban influences to the abundance of fresh seafood, means there's no shortage of amazing cuisine. It is impossible to try every place and the beauty of Key West is once you visit, you just want to go back again and again. Do not skip Blue Heaven We love it for breakfast where the crowd is mellow and hungry for Key Lime Hollandaise on their eggs. The vibe, which also includes wandering chickens, is like an artsy backyard in the tropics. Cuban Coffee Queen has two locations and some of the best Cuban coffee you can find in Key West. It's uber-casual and quick, meaning you can feed your hungry kiddos on the fly while upping your colada (strong Cuban coffee served with sweet cream) intake in style. Look for the location off Key Lime Square for real hidden gem.

#5 Wandering Roosters

It's not at all uncommon to see a rooster dash across as frequently as squirrels in Central Park. Chickens and roosters roam free, along with the occasional cat. Animal-loving kids will fit right in here. 

#6 Key Lime Pie

Rule #1 when you're in the Keys: eat Key Lime Pie. And you might even eat it for breakfast. Nearly every place has it, and they all claim to be the best. It's your duty to try them all and compare.

#7 Adventures on Land & Sea

From a sunset sail on the Appledore II to a sunset carnival just off Mallory Square, adventure awaits around every corner. Don’t miss the Key West Historic Memorial Sculpture Garden, an impressive collection of the busts of famous people who lived in Key West, from shipwreck salvagers to confectioners to writers.

#8 Surprisingly Uncrowded Beaches

Maybe it’s because there’s such a variety of indoor and outdoor activities right near by, but we found the beach at Fort Zachary Taylor State Park to be surprisingly uncrowded. While by no means deserted, there was plenty of space to spread out your blanket or rent a couple of lounge chairs and relax (in between sand castle building and pristine-water swims).

#9 The People You'll Meet

From the cat-loving docents at the Hemingway Home to the ticket vendor to the Ghosts & Gravestones Tour, you will meet many a friendly face in Key West. With a unique cultural background, Key West boasts a vibrant sense of community and attracts artists and sailors alike. You never know who you'll meet on the streets of Key West. 

#10 Secret Street Poetry

You'll no doubt be looking up a lot in Key West, craning to see the Victorian-details of the turrets of a historic home, or watching a mermaid weathervane turn with the wind. But don't forget to look down, literally. Throughout the streets of downtown Key West, you'll find poetry embedded. Stop, read aloud, and get your kiddos in on the beatnik vibe. 

Key West Tips & Tricks

It is possible to fly in and out of Key West and not need a car while you are here. There are a number of "hop-on/hop-off" trolleys and buses to take you to sights a little farther afield, though truthfully the majority of the top highlights are within blocks of each other. 

Parents should be aware that the "party town" atmosphere of Key West can come out after dark, especially during peak Spring Break season. We never felt unsafe in any way but the crowd is definitely different after dark, with bar patrons spilling onto the streets and loud music. 

Parking can be tricky in downtown, but there are a number of paid parking lots. If you are driving, make sure you map out the location of more than one because many of the lots are small and could fill up. 

There's no shortage of hotels and B&Bs to choose from. We highly recommend the Oceans Edge Resort & Marina. It is located on Stock Island, the other side of the island from downtown, but there's a free shuttle to and from downtown between 9 a.m. and 11 p.m. The resort is safe, peaceful and has six oceanfront pools! There's a restaurant on-site too, should you decide you need a little late night nosh. 

If you want to explore the rest of the Florida Keys, check out our guide to doing it with the kids in just five days.