Family Vacation in The Keys—A Day in Islamorada

Reinforcing Love & Support

You’re planning a family vacation to the Florida Keys and your family includes small children.

Where do you go?

You could follow the Overseas Highway all the way to the end and lose yourself in the romance, mystique and anything-goes Hemingway lifestyle of Key West.

Sounds great—if you’re with friends or your significant other. But remember: You’re bringing the kids. And if you’d rather not have to explain to them why the bald, barrel-chested biker with the bushy mustache is wearing a bra, maybe you’d like to rethink your plan.

Think Islamorada.

Islamorada means “Purple Isle” but it’s not one single key. It’s a village stretched over five keys. Statistically, its residents are far less likely to be biker dudes than working couples raising children. It feels more like Buffett’s Keys than Hemingway’s.

And it presents many tourist options. Here we suggest two of the best, plus a great place to eat on the way back—all within the confines of 3 miles. Let’s start with the most distant stop.

Theater of the SeaTheater of the Sea

There may be no more entertaining or enriching family activity in all of the Keys than visiting this marine park at Mile Marker 84.5 and swimming with the dolphins.

Theater of the Sea also offers snorkeling cruises and other adventures, all described at Theater of the Sea. But it’s most famous for its dolphin, sea lion and stringray swims, which have drawn more than 200,000 participants.

Get a “kiss” or “hug” from an Atlantic bottlenose, then hang onto a fin and go for ride. Younger children can enjoy wading with dolphins in shallower waters.

Maybe you’d rather try steadying a hoop while a California sea lion jumps through it. Maybe you’d rather snorkel among the gentle stringrays and feed them in a shallow lagoon. Or maybe you’d rather not hop in the water at all, in which case you can mingle with dolphins or sea lions from dry land instead.

Whatever sessions you choose must be reserved in advance by calling 305.664.2431. Swimming sessions are available mornings and afternoons but dry land interactions are afternoon-only.

The Florida Keys History of Diving Museum

Florida Keys History of Diving MuseumYou won’t have trouble spotting this museum. It’s on your right only 1 1/2 miles away as you head back toward The Hammocks at Marathon, at Mile Marker 83. Just look for the 200×13- and 60×30-foot exterior mural depicting endangered undersea Florida species. Painted by world-renowned mural artist David Dunleavy and legendary marine life artist Guy Harvey, this painting is the largest environmental mural in the Florida Keys.

Inside you’ll find the largest collection of diving equipment and artifacts in the world. Room after room tells the story of man’s quest to learn the secrets of the sea. Guided tours are available only to large groups, so explore at your own pace. Follow a timeline that traces the history of diving to almost 3,000 B.C. Track the evolution of gear from ancient to current. Compare helmets from around the world. Browse the photos, books and documents. Watch films. Examine sunken treasures. Your kids will be far from bored thanks to interactive displays they can immerse themselves in.

If you manage your time right, you can fit this museum into your day even though it closes at 5 p.m. on most days. Admission prices are reasonable at The Diving Museum.

Islamorada Fish Company

By now, undoubtedly you’re ready for sea treasures of the edible kind—and quickly. Luckily, Islamorada Fish Company is minutes away at Mile Marker 81.5.

The restaurant and seafood market, now part of the Bass Pro Shops® family, is the expansion of a marina snack bar opened in the 1940s. The menu today, as then, features fresh local seafood. From your table, you might even be able to view the daily catch unloaded at the dock.

Florida Keys VacationLocal specialties include the Grouper Reuben and other indigenous sandwiches, platters, soups and salads. There’s no children’s menu per se, but if the kids are finicky about fish, feed ’em a cheeseburger. And just for fun, wait until they’ve raved about the appetizer before telling them they’ve eaten alligator.

Now you’re on your way back to your overnight accommodations. You’re tired, but the drive will pass quickly as you relive the fun you’ve had.

But if you’re intent on Key West …

Now, if after enjoying Islamorada you’d still like to enjoy a small, family-friendly dose of Key West, a great way to sample the mostly sweet, sometimes spicy flavor is to ride the Conch Tour Train.

Sloppy Joe's Bar Florida KeysThe narrated, 90-minute tour makes three stops. The first, at Station Depot, gives riders 10 minutes to hop off and grab an ice cream or brick of homemade fudge. The second stop drops you off at Truval Village, at the corner of Duval Street and Truman Ave. Take a jog to see Hemingway’s home, the Key West Butterfly and Nature Conservatory and the Southernmost Point. And last but not least, is the final stop at Flagler Station.

Trains run 30 minutes apart all morning and afternoon. Check the website for info on parking and a complimentary shuttle.