We were immediately hooked.
My husband, Jonathan, had been looking for the perfect opportunity to take our 3-year-old daughter, Lucy, fishing for the first time. When we arrived at Cheeca Lodge & Spa on Islamorada in the Florida Keys, we discovered that the hotel had pint-size fishing rods for kids.
Within seconds of casting a line off Cheeca’s pier, Lucy pulled in a little fish. It was so small that we immediately threw it back, but she was delighted.
We’re always looking for a family getaway that isn’t too far from home, has kid-friendly accommodations, and offers plenty of entertainment for children and adults.
Islamorada checked off all those boxes — and then some. Here are the 10 reasons why this beachy vacation spot is perfect for kids.
1. Its location in the Florida Keys
The great thing about Islamorada is that it’s halfway into the Keys. (The iconic Midway Cafe at mile marker 80.5 indicates the “midway” point.) So you’re well located if you want to take a day trip to Key West, but not too far from the mainland.
Set between Everglades National Park and the deep-blue Florida Strait, Islamorada is actually a string of six islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, as well as offshore Indian Key and Lignumvitae Key. This means you’re surrounded by an aquatic paradise, with ocean on one side and protected waters teeming with marine life on the other.
Father and daughter fishing off the pier at Cheeca Lodge. (Photo: Laura Begley Bloom)
Islamorada is known as the sportfishing capital of the world, and even Ernest Hemingway came here back in the day. You can charter a boat or fish just about anywhere: off the shore, off a dock, off old railroad bridges. The easy angling makes it great for both grownups and guppies. Cast a line and your kids will be reeling in everything from snappers to ladyfish in no time.
Want to introduce your kids to the species of the area? Stop by the sprawling World Wide Sportsman (mile marker 81.5), which has a saltwater aquarium in the middle of the store. (Kids also love climbing on the store’s wooden boat, sister of Hemingway’s Pilar.)
Cheeca Lodge, on a sliver of land in the Florida Keys. (Photo: Cheeca Lodge & Spa)
3. Cheeca Lodge & Spa
Jonathan and I visited Islamorada a few years back and stayed at a hip boutique hotel called Casa Morada. This time around, we chose the more classic Cheeca because of all that it offers families — from movies under the stars to snorkeling expeditions to bikes for exploring the lush, 27-acre property with its hidden lagoons.
The kids’ club, Camp Cheeca, has plenty of programming — scavenger hunts, dance parties — to keep the young ones busy. The drop-off sessions are for children 5 and up, but the club still let Lucy come by to paint coconut shells and play on the new jungle gym.
The hotel turns 70 this year and has tons of history around every turn, including an old graveyard where some of the founding families of Islamorada are buried. Fun fact: Cheeca’s first guest was none other than President Harry Truman.
Exploring the beach at Cheeca. (Photo: Laura Begley Bloom)
Narrow, sandy beaches line Islamorada, and thanks to the warm, calm — and shallow — waters, they’re perfect for kids. Cheeca is smack-dab on a 1,200-foot-long private beach that is flat enough for biking. Founders Park has tons to do, including a skate park for older kids and a heated pool where you can watch movies after dark. (Bring your own float.) A boardwalk stretches along Anne’s Beach, which has picnic tables for an afternoon repast. Another fun destination: white-sand Islamorada Beach, which is actually an offshore sandbar near Holiday Isle that you can only reach by boat.
This pelican found a fine place to roost. (Photo: Laura Begley Bloom)
5. The birds
Lucy loved chasing the pelicans on Cheeca’s pier and spying the egrets lounging on the hotel’s golf course. The Keys are known for stellar bird watching, and Islamorada in particular is a natural habitat for many species. Owls and gulls, herons and hawks — you’ll find them here. Take the kids to the Laura Quinn Wild Bird Sanctuary on nearby Tavernier, where they can see birds that have been rescued and brought back to life.
Dockside dining and a spectacular sunset at Lorelei. (Photo: Lorelei Restaurant & Cabana Bar/Facebook)
6. Waterfront restaurants
Islamorada is ground zero for beach restaurants and tiki bars. Live music, killer sunsets, and stone crabs are the draws at dockside Lorelei Restaurant & Cabana Bar, which will also cook the fish you caught that day. The colorful, Caribbean-style Morada Bay Beach Café has tables right in the sand; its sister restaurant, Pierre’s, is a more elegant affair (think blue crab vichyssoise) set in a West Indies-style plantation house. And at Cheeca, the waterfront Tiki Bar serves up fresh lime-agave margaritas, mojitos, and perfect conch fritters.
A huge and hungry tarpon at Robbie’s. (Photo: Jonathan Bloom)
7. Feeding the tarpon at Robbie’s
One thing not to miss is Robbie’s at mile marker 77.5, where kids will get a kick out of feeding the tarpon. You pay a $1 admission to get on the dock itself, then another $3 for a bucket of chum. The massive fish leap out of the water to grab the bait. Watch out: Those suckers have teeth!
Listening to the ocean at the Shell Shack. (Photo: Jonathan Bloom)
8. Shell shops
There’s nothing like a kitschy shell shop to get a kid excited (and me too). Shell shops line the highway, but my favorite is the open-air Shell Shack, with rows and rows of conchs and more. Lucy and I spent forever wandering around while she picked out the perfect souvenir.
A slice of goodness at the Midway Cafe. (Photo: Midway Cafe)
9. Key Lime pie
What’s a visit to the Keys without a slice of Key lime pie? The not-so-secret ingredient is (shocker) Key lime, but they’re surprisingly hard to find, even in the Keys. Less so in Islamorada, where some locals grow the fruit in their backyards. The jury is out on the best slice in the area, but some of the contenders include the Midway Cafe (which serves a legendary local recipe from the now defunct Manny & Isa’s), Ma’s Fish Camp, Lazy Days, and the Green Turtle, with its funky neon sign out front. Go on a Key lime pie crawl and decide for yourself.
Sunset at Pierre’s. (Photo: Jonathan Bloom)
Islamorada means “Purple Isle” in Spanish — the early settlers were inspired by the purple hues of the sunsets here. For the best spectacle, head to the bayside. Most tourists flock to Lorelei. My personal pick? Pierre’s, which is much more sedate and where the palms perfectly frame that sunset photo op.
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