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Insider’s Guide to Islamorada, Florida Keys

By Becky Strauss

The Florida Keys are a 120-mile-long chain connected to the mainland by the two-lane U.S. 1. And they’re the closest thing we’ve got to the Caribbean, with dive-able coral reefs, sport fishing, mangrove kayaking, beach bars galore, and a kick-back culture that’ll put you in a flip-flop state of mind. Near the top of the keys is Islamorada (pronounced EYE-la Morada) a world-famous sport fishing spot with tons to offer both on and off the water.


Where to Stay

The Postcard Inn Beach Resort & Marina at Holiday Isle (PCI) has been around since 1951, but was reborn in January 2012 as a chic resort with a mid-century modern meets New England-boathouse vibe (Rates from $169/night). Retro rooms feature driftwood floors and hand-painted quotes. Famous for its formerly raucous parties and for inventing the rum runner at the onsite Tiki Bar, which is still there —and still rocking — the resort has mellowed into a family friendly spot with plenty of diversions like jet skiing, kiteboarding, scuba diving, or just lounging by the pool.


What to Do

Fishing needs are well taken care of at Holiday Isle Marina, where you can either rent your own boat or go with a guide (from $450 to $1,600 per trip). Onsite Islamorada Watersports Company rents kayaks, jet skis, stand-up paddleboards, and the like; the onsite dive shop offers two trips per day. The Morada Way Arts and Cultural District is a collection of studios and galleries filled with local art; there’s a “third Thursday walkabout” every month when each stays open late. Also nearby are a number of state parks, both under and on the water.

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Where to Eat

For such a small island, there’s a lot of variety on Islamorada. Your first stop should be cocktails at Morada Bay Beach Cafe, on the inlet side of the island. The sand’s not deep, but it’s wide, and there’s live music most days, as well as an excellent tapas menu, raw bar, and entrees like whole fried snapper.

Then, Jaws Raw Bar at PCI offers a tasty seafood menu, with favorites like conch fritters and popcorn shrimp, overlooking the ocean—just keep an eye out for the pelicans who’ll be watching your every move.

The deck of local institution Lorelei Cabana Bar and Marina is the place to catch the sunset. There’s live music to see the sun down seven days a week, as well as a menu chock full of fish-centric fare. Despite the proximity to the water, we recommend their baby back ribs and juicy burgers.

How to Get There

By Car

If you’re driving from Miami International Airport take LeJeune Rd. south to 836 West. Get on the Florida Turnpike south towards Key West; it ends at US 1 in Florida City, which you’ll follow south to Islamorada.

From Ft. Lauderdale-Hollywood International Airport, follow the signs for 595 West; take that to the Florida Turnpike and follow signs for the Florida Keys. From Florida’s west coast, take I-75 (Alligator Alley) east to the Miami exit and south to the Keys.

By Air

You’re about an hour and a half from Islamorada if you fly into Miami International Airport; fly into Fort Lauderdale International and you’ll add about an hour of driving time. Alternately, you can fly into Key West International Airport and drive up; that’s also about an hour and a half.

Thinking of a trip to Florida?

For up-to-the-minute hotel and restaurant recommendations, as well as the best planning advice, check out our Florida Travel Guide.

Photo credits: Islamorada Beach via Shutterstock; Postcard Inn Holiday Isle courtesy of Postcard Inn; Jet Skiing via Shutterstock; Jaws Raw Bar courtesy of Postcard Inn

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