Islamorada Idyll

The True Keys Are Closer Than You Think

The palms overhead swayed lightly. A gentle breeze made ripples across the surface of the pool. Other than a few distant mockingbirds and the sound of the palm fronds rustling, everything was silent. I twirled my glass of wine and took a sip. This was more than a vacation. This was an escape.

When you think of the Keys, it’s easy to imagine sunburnt tourists in Key West stumbling down Duval Street in a rum-runner-induced haze. But the rest of the Keys are much more local, relaxed, and less centered on drunken shenanigans. Islamorada, about two hours south of the Gables on Plantation Key, is famous for its small-town feel, easy access to the water, and bevy of upscale boutiques and restaurants.

I started my trip by arriving at The Maison Residences, a set of luxury vacation rentals that rival any major resort. Once you turn onto Old Highway and enter the gates, you’re in your own private world. Complete with pool, private beach, and dock, it’s tempting to spend your whole time here.

The property has just four buildings with 21 residences. Rentals range $5,000 to $15,000 per week. Two of the buildings were built just a couple of years ago — they even still smell new. According to Patti Stanley, owner of the Island Villa Rentals, each of the buildings has its own unique design. The one I stayed in had a West Palm feel: all-white furniture and cabinets, modern, beachy decor, with a fantastic view from the balcony.

One of the best ways to travel around Islamorada is by golf cart, especially if you stick to Old Highway. Plus, bopping around in a golf cart adds to Islamorada’s cozy feel. You can rent one at Kokomo Carts ($875/week).

Lucy de la Vega displays her work at the Morada Way Art Walk.

I was lucky to arrive on a Thursday when the Morada Way monthly art walk was in full swing, so I drove my golf cart over. The Morada Way Third Thursday Art Walk occurs every — you guessed it — third Thursday of the month. Vendors from across South Florida display handmade crafts, jewelry, and Keys-inspired art. While there, I ran into Coral Gables resident and jewelry designer Lucy de la Vega. You can find her work at Brenda Noy in the Gables.

De la Vega only recently started coming to the art walk. She says one of her favorite things is the people, a mix of Keys locals and tourists. From 6 to 9 pm, the art walk is in full swing; afterwards, most visitors migrate to the Florida Keys Brewing Co.

Florida Keys Brewing Co. is the type of place you think of when you hear a Jimmy Buffet song, as in laidback. I ordered a brew at the bar and headed out back to the beer garden, which felt like my best friend’s backyard. Fairy lights surrounded the beer garden and snaked up every tree. Candy-colored wooden tables were filled with happy patrons, while live music played. I sipped an “Iguana Bait,” a Kolsch-style beer made with hibiscus and local honey.

The Florida Keys Brewing Company
The Florida Keys Brewing Company

Islamorada actually has a lot to do. It is the self-proclaimed sportfishing capital of the world, and it’s well-known for paddle-boarding, kayaking, kiteboarding, and other watersports. I headed over to oTHErside Boardsports to rent a paddleboard for the day ($60/day, $195/week). Owners Mike and Shana Walsh recommended I check out Anne’s Beach, so off I went.

Few things are more relaxing than paddling in crystal clear water while a light breeze blows at your back. Anne’s Beach is a must for nature lovers and water athletes. On windy days, kiteboarders flock there; on calmer days, it’s paddleboard paradise. After working up an appetite on the water, I headed to one of Islamorada’s best-known outposts, Robbie’s Marina.

Part restaurant and open-air market, part tarpon-feeding spot and fishing charter hub, Robbie’s is Islamorada’s one-stop-shop approach to tourism. Famous for the population of tarpon surrounding its docks, Robbie’s is a huge draw for out-of-towners, but a lot of local fishermen hang out at its bar to talk about their day on the water. It’s a must for people-watching, strong pours, and the ever-popular feeding of tarpon.

Robbie’s, part restaurant and outdoor market, is popular with tourists and local fishermen.

Toward the end of my trip, I sat on my balcony and gazed at the ocean, watching the sky turn from yellow to orange to pink and finally purple. Islamorada might not hold the history and antics of Key West, but it’s perfect for a little escape.

The Maison Residences

80639 Old Highway
Islamorada, FL Keys 33036
Bookings: Patti Stanley
Direct: 305.664.3333