A Weekend in Islamorada
Luxury resorts, sunset celebrations, and kitschy old Florida charm just two hours from Miami
Miami is known for its cosmopolitan days and vibrant, neon-filled nights but if you’re longing for a true taste of Old Florida hospitality, you’ll find it in the Florida Keys.
And, while Key West gets the lion's share of celebrity for its bars, history, and Hemingway ties, Islamorada is your destination for lovers of sunset celebrations and water sports.
Known as the “sportfishing capital of the world”, Islamorada is more than that. Consisting of six islands in the Florida Keys, Islamorada is home to over two dozen restaurants, several breweries, coffee houses, parks, attractions, marinas, and resorts.
Keys life revolves around the water, and visitors to Islamorada can find their own paradise whether it be sport fishing, snorkeling, or watching the sun dip into the bay. Here are the best places to check out in Islamorada.
Where to Stay
This coastal chic resort is part of the Islamorada Resort Collection of four hotels including the Pelican Cove Resort & Marina, the Postcard Inn Beach Resort & Marina, and La Siesta Resort & Villas. Of all four, Amara Cay feels the most like a boutique hotel with beautifully appointed rooms and suites equipped with a Keurig coffee maker, microwave, and fridge. The best part is that guests of any of the four hotels can use the amenities of all four resorts including bikes, kayaks, and pools. Amara Cay’s sister hotel, Postcard Inn is home to the Florida Keys’ favorite Tiki Bar. Amara Cay also offers a tiki bar experience, adjacent to the pool and the ocean for perfect views.
Where to Eat
Sunset celebrations are a popular activity in the Florida Keys and you’ll find no better place to watch the end of another glorious day than at Marker 88. This restaurant is the epitome of “barefoot elegant” with many tables actually located directly on the sand. Marker 88 offers fresh seafood and craft cocktails. A favorite is a key lime seafood platter of local shrimp, crab legs, and lobster tails over fragrant cilantro-lime rice. Market 88 also offers fresh sushi and craft cocktails — the Hemingway daiquiri is especially appropriate during sundown. If you’re traveling with your four-legged friend, there’s an entire dog-friendly wing or, if you simply want to enjoy a few drinks, two tiki bars allow you to enjoy the views with a cocktail in hand.
For decades, Safari Lounge was the watering hole of choice for both locals and visitors in the know who would stop for a drink at the “Dead Animal Bar”. The bar received its slightly macabre nickname for the display of animal trophies mounted on its walls. Hurricane Irma caused significant damage in 2017, and the bar remain closed until it reopened as Oceanside Safari just last month. You’re greeted by a lion, a giraffe, and a hippo — these new wildlife are animal friendly and made of wood. Inside, giant picture windows allow for panoramic views of the ocean. Or, opt for a table outside. Chow down on local seafood — including homemade fish dip, burgers, and salads. Oceanside Safari also offers craft beers brewed just up the road, wines, and a full cocktail program.
Loved by locals and visitors, Square Grouper offers fresh seafood and steaks in a resort-casual setting. Though the restaurant is modern and spacious (and an indoor dining room offers some much-needed respite from the sun after a long day boating), locals “in the know” arrive at 4:20 p.m. on the dot for the opportunity to snag a barstool at the upstairs speakeasy on the third floor. The 4:20 opening? It’s a nod to the restaurant’s name: Square grouper is the name for the floating bales of marijuana that were picked up by boats in Miami’s drug-running heyday in the 80s.
Where to Drink
This modern brewery and distillery offers locally brewed beers and cocktails made with locally distilled spirits. Core beers include Sandbar Sunday, a wheat beer that’s a perfect beach pounder, and Channel Marker IPA — but you simply cannot leave the Keys without a pint of the No Wake Zone coconut Key Lime ale. Islamorada also distills its own spirits including a pea flower hibiscus gin. The brewery also has a beer garden in back, along with a food truck serving light bites.
Florida Keys Brewing Co. is a colorful indoor/outdoor brewery that features freshly brewed local beers like the Iguana Bait hibiscus kolsch and the Smelly Butt American IPA. A huge beer garden offers food from rotating food trucks, live music most evenings, and dog-friendly theme nights.
This multi-use complex (part marina, park restaurant, part bar) comes alive during sunset with live music, cocktails, and fishing charters. Whatever you do, don’t sleep on the Key Lime colada — a frozen cocktail that’s sweet/tart and potent for the perfect tipsy brain freeze.
What to Do
Is Robbie’s a tourist trap, a marina, a restaurant, or an art gallery? The answer is “yes”. At Robbie’s, you can eat and drink at one of its many bars, shop for art and crafts from locals, and rent a kayak to explore the mangroves. But the main attraction is feeding the tarpon. For $2.50 (and an additional $5 for fish), you can access a pier where giant tarpon gather for free meals provided by sunburnt visitors.