Named Islamorada ("purple island") by the Spanish in the late 1800s, this tropical Florida island has been a destination for legendary storytellers including Zane Grey and Ernest Hemingway ever since.
In the mid-1940s, a small inn called Olney Inn opened right smack on the Atlantic. The first guest was President Harry Truman, followed shortly thereafter by Edward Murrow and many a political Washington elite. Frequent transformations of the lodge brought avid fishermen from all around the world, with perhaps the most famous angler President George H.W. Bush, who came so often he established an annual Bonefish Tournament raising thousands of dollars for various charities.
A Miami Herald newspaper reported, “Here is the fishing ground of the world, where strikes are as frequent as sunny days and specimens that would be record catches in other parts of the world are tossed disdainfully overboard to grow up.”
Today this inn is a world-class resort and spa, Cheeca Lodge. It's the perfect spot for an unforgettable family vacation. Trust me when I say that you’ll find every comfort, every delicious morsel you could desire at Cheeca.
But here’s what I want to tell you: You and your children can choose from more activities than I have room to write about — snorkeling to North America’s only living coral barrier reef; paddling through the Everglades in a sea kayak for amazing wildlife viewing; fishing with a skilled captain who will prioritize your family’s safety and fun; parasailing to touch the clouds; windsurfing; paddle boarding while enjoying the beauty of the Islamorada waters; joining Camp Cheeca, a day camp, learning about wildlife and marine habitats in the Florida Keys. All of this happily is arranged by the staff at Cheeca.
Off resort: Pretend you’re Captain Nemo as you navigate the exhibits at the History of Diving Museum; enjoy an island ride in a Clydesdale horse-drawn carriage; meet a dolphin or ride a Bottomless Boat at the Theater of the Sea; stroll through the Florida Keys Wild Bird Center; rent a Tiki Jet, the world’s first water-powered jetpack taking you airborne for 15 to 30 minutes; and visit San Pedro Park, the final resting place of one of the 21 Spanish galleons that sank in a 1733 hurricane.
For off-resort dining: The Green Turtle is a breakfast must, for coconut French toast and keys benedict with blue crab cake. The Lazy Days Restaurant is oceanside, kid-friendly, fun and delicious. The Lorelei Cabana Bar & Restaurant is the place to enjoy conch chowder, live entertainment and brilliant sunsets.
Pierre's Restaurant is for mom and dad’s night out. It’s the most gorgeous island experience. I expected to see Rick sitting at the bar and Sam playing "As Time Goes By” on the piano. Ask for a table on the balcony and enjoy fine dining and the most civilized, enjoyable sunset on the island.
And remember, this is about eating out in Islamorada: Most, but not all, of the restaurants will cook your catch and you must — absolutely must — have at least two or three pieces of key lime pie before you leave.
Shopping is as funky and laid back as the island. Look for the gigantic lobster out front of the Rain Barrel Artisan Village, where you’ll find kitschy island stuff. Latitude 25 Clothing Co. will outfit you and the kids in swimwear, sandals and Tommy Bahama. And for the ultimate in fishing gear, there’s a truly outstanding Bass Pro Shop.
You could spend all day here, enjoying the lovely art gallery the Zane Grey Lounge and perusing the Pilar, sister ship to Ernest Hemingway's beloved boat.
Grab the kids and a bucket of bait or some fancy fishing lures and try your luck in the "sport fishing capital of the world." The fish won’t care — or, as President Herbert Hoover once said, “All men are equal before fish.”