Named Islamorada (Purple Islands) by the Spanish in the late 1800s, this tropical Florida island has been a favorite destination for legendary storytellers like Zane Grey and Ernest Hemingway. In the mid-1940s, a small inn called Olney Inn opened right smack on the Atlantic. Its first guest was President Harry Truman, followed shortly thereafter by Edward R. Murrow and other political Washington elite. Frequent transformations of the lodge brought avid fishermen from around the world, including perhaps the most famous angler, George H. W. Bush, who came so often he established an annual Bonefish Tournament raising thousands of dollars for various charities.
Today, the inn has been transformed into a world-class resort and spa, Cheeca Lodge—the perfect spot for an unforgettable family vacation. Trust me when I say that you’ll find every comfort and every delicious morsel you could desire at Cheeca. But here’s what I really want to tell you: You and the your children can choose from more activities than I have room to write about. There’s 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, parasailing to touch the clouds, windsurfing, paddle-boarding while enjoying the beauty of the Islamorada waters, and joining Camp Cheeca to learn about wildlife and marine habitats in the Florida Keys—all happily arranged by the lodge staff.
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 Underwater Archeological Preserve State Park, the final resting place of one of the 21 Spanish galleons that sank in a 1733 hurricane.
For off-resort dining, Green Turtle Inn is a breakfast must, for Coconut French Toast and Keys Benedict with Blue Crab Cake. Lazy Days Restaurant is kid-friendly, fun and delicious. Lorelei Restaurant & Cabana Bar is the place to enjoy conch chowder, live entertainment and brilliant sunsets. Pierre’s Restaurant is for Mom’s and Dad’s night out. Ask for a table on the balcony and enjoy fine dining and the most civilized, enjoyable sunset on the island. And remember this about eating out in Islamorada: Most restaurants will cook your catch; and you absolutely must have at least two or three slices 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 Company 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 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 Herbert Hoover once said, All men are equal before fish.