For the best of both the beach and boating, book a villa at Hadley House, which is located near the center of Islamorada. This recently remodeled boutique resort (from $150) is set up near some of the Key’s most popular restaurants and attractions, with cocktails, water sports and other activities like breweries and museums all less than a five-minute drive away. With a location practically sitting on the sand, guests of the hotel can take advantage of complimentary on-site kayaking and paddle boarding or (for an added charge) a private jet-skiing tour of the surrounding keys. The Cheeca Lodge & Spa is another popular resort, offering tropical-inspired rooms, a nine-hole golf course and a full-service spa on a secluded beach with a fishing pier (from $200).
We promised beaches, so here you go: Founders Park in Islamorada features 45 acres of clear coastline, with shallow turquoise waters, plenty of sand and palm trees to lounge under for an afternoon. Then, check out the History of Diving Museum, which features one of the largest collections of diving artifacts in the world. Speaking of which, the Theater of the Sea is the world’s second oldest marine mammal facility, where you can swim with dolphins, California sea lions and stingrays. Swing by Islamorada’s growing arts district too, which includes numerous galleries such as Pasta Pantaleo’s and Michelle Lowe’s. If you’re lucky, you may be able to catch the Morada Way Third Thursday Art Walk, which features live music, food and local art. But above all, book a sunset sail at Robbie’s Marina, home to its world-famous tarpon feeding, shopping and food. You’ll cruise along the open ocean for nearly two hours, catching one of the most picturesque sunsets in Florida. (Oh, and the boat is always stocked with free Champagne.)
Unsurprisingly, seafood reigns supreme in Islamorada. Some of the freshest catches can be found at Lorelei Restaurant and Cabana Bar, where the setting is next-level (you’ll literally eat dinner on the sand facing the water) and the food is out of this world. Get there 30 minutes before sunset, order a margarita and pair it with smoked fish dip and a blackened snapper sandwich. Other noteworthy island restaurants include Midway Café and Coffee Bar for breakfast and brunch, Green Turtle Inn and Chef Michael’s for something slightly more upscale, and the Hungry Tarpon at Robbie’s Marina, which is home to the best blackened hogfish sandwich ever.
Get this: Islamorada is home to not one but two funky breweries worthy of a visit. Florida Keys Brewing Co. (try the best-selling Iguana Bait) and Islamorada Beer Company both brew local beers with Keys-inspired ingredients, from key limes to starfruit and honey. You’ll also want to stop by Hog Heaven, a waterfront sports bar known for live music, stiff margaritas and sweet sangria. If your schedule allows, spend a few hours at Florida Keys Brewing Co.’s outdoor beer garden, which also features live music a few nights a week.
