A mere 80 mile-drive South from Miami International Airport, you’ll find the cozy and relaxing charm of Islamorada. The journey along green mangrove-lined US 1 (also known as the “Overseas Highway”) brings you to the northern part of the Keys, the island chain that forms a narrow spit separating the turquoise waters of the Florida Bay and the Atlantic Ocean.
I’ve always driven through Islamorada thinking there was nothing worth stopping for between Miami and Key West, but I was pleasantly surprised. I’d always thought of it as a rather nondescript destination, aside from beautiful beaches, trying to “out-Key” its neighboring islands with a bigger conch shell or giant lobster in the driveway. For the past 30 years the roadside billboards have advertised t-shirt and sandal outlets, and it has historically prided itself in being “rustic” and super-casual aside from two or three high-end resorts. But as I learned, the tourism bureau and chamber of commerce made a concerted effort over the past few years to renovate several simpler hotels, as well as create a historic arts district with higher-end galleries, boutiques and restaurants.
Islamorada (named by the early Spanish explorers “Purple Isle,” perhaps because, according to fishermen’s legend, the waters turn an amazing purple at night) has become a very hip destination for couples, families, sports fishermen, boaters, snorkelers, scuba divers and land lovers alike. The palm-lined pristine beaches, calm clear Caribbean seas, luscious tropical vegetation and proximity to island activities such as freshly refurbished accommodations, excellent restaurants, breweries, a whiskey bar, numerous cafes, and an art district walk, make this an ideal place to spend a long weekend.
Island Resorts Company has recently revamped a few hotels and resorts. There is the more relaxed, family-oriented, bright and airy Pelican Cove with its poolside Wild and Lime restaurant situated right on the beach overlooking the lagoon, and its highlight, the marina for boaters and sports fishermen.
My favorite place to stay is the completely renovated Amara Cay with its understated elegance, inviting decor and friendly, gracious service. The muted light colors, reclaimed wood, rattan and green tropical plants throughout remind me of a beach cottage, and the playful hanging papasan chairs in the lobby and bar area invite a relaxed intimate social atmosphere. I had a spacious ocean-view suite and particularly enjoyed waking up in my very comfortable bed to the sound of the ocean waves lapping gently on the beach below my balcony (I had left the doors open overnight to enjoy the sea breezes). The hotel features an excellent gourmet restaurant Oltremare, where Chef Dario serves creative Italian food with a fresh Florida twist. I had the locally caught cobia on melted leeks with candied carrots, followed by Zeppoli Italian doughnuts with Nutella sauce…delicious!
Michelle, one of the supervisors, was most helpful and knowledgeable, sharing some of the island’s geography as well as where to go and what not to miss. Apparently Islamorada is in fact four islands, which include Plantation Key, Windly Key and Upper and Lower Matecumbe Keys. The complimentary hotel’s Mercedes Benz sprinter is a practical way to get around the island attractions such as Oo-tray’s whisky and bourbon bar, with casual “global” dining and live music on the patio, or the historic Morada Way Arts and Cultural District with charming galleries and the now famous Florida Keys Brewing Company, one of two local breweries. Though I was caught up in enjoying the beaches and food, there are some very nice boutiques for fashion and swimwear (Lion’s Liar).
Just north of my hotel, exactly halfway between Miami and Key West, there’s the charming family-run Midway Cafe for all-day brunch, featuring freshly baked pastries, organic (and vegan) dishes, as well as fresh-pressed juices and a wide variety of creative coffee drinks. It also makes arguably the best Key Lime Pie in the area!
Per Amara Cay’s helpful concierge, I grabbed a table in the sand at the Morada Beach Café for a freshly pressed pineapple juice and breathtaking view of the Keys sunset. The pelicans glided by the tranquil afternoon sky, the winds having died down so much that the water was flat as glass. It was hard to distinguish where the ocean and sky met, the little emerald islands seeming to hang suspended in mid-air.
There are two serious sea-to-table restaurants, the elegant Pierre’s located in a two-story white plantation house with wraparound verandas overlooking Morada Bay, and the award-winning Chef Michael’s across the street, one of the few Keys restaurants owned and operated by the chef (and the food is excellent!). Reserve early in the day as the smallish place is constantly packed. Many guests bring their own freshly caught hogfish, grouper, snapper, swordfish and tarpon and have it mouth-wateringly prepared. Prime meat and game are also exquisitely featured. The wine cellar seems to be seriously stocked as I sat eating at the bar between two California vintners and they were very happy.
A fun-family oriented activity is going down a couple of miles to Robbie’s Marina to feed the tarpon and pelicans, then enjoy a wide range of recreational marine activities such as renting kayaks, pedalos, planning fishing, diving and scuba trips, or enjoying a boating excursion. (Of course the staff at Amara Cay will also happily do this for you.) Robbie’s is also famous for its salty Keys-style bar and restaurant on the water that serves Caribbean-inspired cuisine.
I loved my time in Islamorada and was happy to discover how, over the past few years, it has grown up, becoming more sophisticated without losing any of the exquisite beauty of the Keys and gaining so much charm and style. The ‘cool Key’ is a perfect getaway for a long weekend to relax, restore, and nurture body and spirit.
Be inspired: Florida Keys Travel