Islamorada, Florida Keys

In the 16th century, Spanish conquistadors came upon a thin stretch of land within a longer belt trailing off the Southern end of what became Florida. There they witnessed some of the most intense sunsets of their journey, and so they christened the land Islamorada, literally “The Purple Isle.”

Five hundred years later, Islamorada is one of our favorite places, too. And the sunsets, though just as spectacular as advertised, are just one reason. I’ve been going there almost every summer since I was seven when it was still a sleepy fishing village.

The town has grown up in the last thirty years, with more visitors, more resorts, cooler shops, and better restaurants. But since the 1880s when homesteaders known as Conchs first arrived, the island has somehow kept a vintage charm balanced with modern luxuries. Here’s our insider guide to Islamorada for an uncommon and adventurous visit to the “best” Florida Key.

Sport Fishing: Cloud Nine Charters

Islamorada is widely known as the sportfishing capital of the world, where bayside or oceanside you’ll enjoy an array of fabulously memorable targets. Our favorite fishing charter is Captain Greg Eklund, who’s fished around the world and been featured on ESPN’s Walker’s Cay Chronicles, Flip Pallet’s Fishing the Keys, and Fox Sports Reel Adventures.

Aboard his the 48-foot custom “Cloud Nine” or 16-foot “Little Nine” Hells Bay flats skiff, we fill up the phone with loads of memorable catches, as he quietly teaches our family everything we want to know about deep-sea or inshore fishing and simply puts you on fish after fish. While hunting fish, don’t forget to pack and apply safe sunscreen to protect your skin from direct and indirect sunlight.

Exploration: Indian Key Historic State Park

Found on an eerie 11-acre island that boasts excellent snorkeling along a long ago coral reef, a Spanish settlement thrived on Indian Key until the mid-19th century when Seminole Indians attacked, either killing or driving away all the settlers.

Today you can explore gravesites and town ruins in an almost apocalyptic experience. Since there’s no freshwater on the island, mosquitoes are practically nonexistent, but with harsh sun and no modern conveniences, bring water in a reusable bottle, wear a long sleeve sun shirt and wear a good sunscreen.

Pro Tip There are no bathrooms or trash cans on the island, so bring food and drink with minimal packaging. The park is only accessible by boat or kayak, and there is a small per-person fee per to enter the island.

Lunch: Robbie’s

Near Indian Key, Robbie’s is one of those rare places where the view is great, the food is tasty, AND there’s more to do than just eat. In 1976, Robbie Reckwerdt and his wife helped an injured silver king tarpon they named Scarface. The fish stayed, then invited friends.

And now you can feed whole schools with a bucket of baitfish for only $3 before enjoying a festive lunch at the Hungry Tarpon, where Trailer Trash Bloody Mary’s and fish tacos rule the menu. While waiting for a table or after the meal, cruise the open-air market showcasing art, jewelry, sunglasses, clothes, and all kinds of uncommon island-feel items. Whenever you wear it back home, you’ll be tempted to ask, “remember that time at Robbie’s?”

Family Activity: Keys Cable

If you want to make uncommon memories doing something friends have likely never tried, go cable wakeboarding at Keys Cable at oTHErside Adventure Park, a 50-acre park containing a five-acre tidal lagoon (with depths up to 65 feet) dredged during the 1900s as the Overseas Railroad was built.

Even if you’ve never heard of cable wakeboarding, Matt and his team will gently guide and inspire you to try (and love) new things. And if you’re an experienced boarder, there’s an advanced cable system. Don’t miss oTHEerside Boardsports, where Mike and Shana can set you up with kiteboard lessons, paddleboard rentals, and eco-tours, and where you can pick up the best sunscreen on the planet.

Outfitter: Bud n Mary’s

Islamorada has lots of spots to outfit your day trip, but Bud N Mary’s is the best, most old school version, visited by locals and tourists alike, where you can find classic keepsakes like the iconic sailfish shirt, and a visit to the tackle shop sets the tone for a perfect day on the water. The Stanczyk family has been running Bud n Mary’s Marina since 1978, and it’s an Islamorada institution.

Stay: Cheeca Lodge & Spa

Since 1946, this 4-star, 214-room resort has offered families and couples alike ridiculously friendly service, first-classing dining, and unfettered amenities like golf, tennis, pools, and a lovely private beach — all set among lush, nature-first grounds. During your stay, check out The Signature Store, where you can find elite clothing and gear that will always remind you of the wonderful time you had.

Extra: The ‘Bloodline’ Tour

Ok, first go watch Bloodline, one the best, most well-crafted miniseries Netflix has ever produced. Then take a trip to Islamorada and seek out locations found throughout the show. Then come home and watch it all again, letting the “hey, we were right THERE” feeling wash over you like a warm Islamorada breeze. You’re welcome.

In Closing

Islamorada is one of our favorite places, where we love the good times in, on, and off the water with our favorite people. A destination for world-class sport fishing, snorkeling, scuba diving, and all kinds of water sports, for a person who loves thriving in the sun, it simply doesn’t get better.

When you’re out enjoying all that water, wind and sun, make sure you’re staying safe with elite, reef-safe sunscreen and eco-friendly sun shirts 100% made with fibers from recycled plastic water bottles (so you can help keep a little bit of plastic out of our marine habitats).