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.
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.