Islamorada is an in-between place, a mix of high and low, American and Caribbean, both refined and edgy. Nestled squarely between booming Miami and rowdy Key West, Islamorada remains more hippy than its northern counterparts, yet more elegant than the infamous sprawl of Key West’s Duval Street.

A row of palm trees on a fine, white-sand beach near turquoise water with small ripples -- a placid beach-side scene in Islamorada, Florida
Welcome to paradise: Islamorada's palm-fringed beaches are part of its laid-back appeal © Corey Jenkins / Getty Images

Often considered a midpoint for travelers on the Overseas Highway, Islamorada is much more than a pass-through. It’s just over seven square miles, but this community boasts a bustling arts scene, five-star resorts, long stretches of wilderness preserves, and an aesthetic all its own.

Instant relaxation

The first order of business when arriving in paradise is to relax – like much of the Florida Keys, Islamorada is a blend of luxury and simplicity. You’ll notice this immediately, with feral chickens roosting in trees next door to carefully manicured lawns. Unwind at the iconic dock of the Moorings Village — which fans of the Netflix series 'Bloodline' will undoubtedly recognize — or the mellow beach at Pines & Palms resort.

Be pampered at Blu Bamboo Salon & Spa, or enjoy a cool beverage in the colorful beer garden at Florida Keys Brewing Company. For some laid-back activities, rent a bike or a kayak from Backcountry Cowboy and take a ride down the quiet Old Highway or glide through the shallow waters around the bayside mangroves.

A woman paddles a kayak on the sea off Islamorada, Florida, as a rainbow lights up the morning sky behind her
Sunrise from a kayak off the Pines & Palms Resort in Islamorada © Kerrick James / Getty Images

The best thing about a place like Islamorada is you don’t need a carefully planned itinerary to enjoy yourself. Just sitting at Anne’s Beach — free and open to the public all year — with the sun shining and the water lapping at the shore is enough to make anyone’s blood pressure drop. Be sure to pick up a beach read at Hooked on Books along the way.

Island flavors

The cuisine in Islamorada defies definition. From high-end French-Caribbean flair at Pierre’s, to sticky buns the size of your face at Bob’s Bunz and delicious Quik Chik fried chicken at the Mobil gas station, there is something for everyone.

With fresh fish caught each morning, seafood is the obvious go-to in Islamorada. You can’t go wrong with mahi-mahi or yellowtail at any restaurant, but for a real taste of the Keys, conch chowder or conch fritters are a must. Keys natives often refer to themselves as ‘conchs’ and their territory as ‘the Conch Republic,’ so it’s no wonder the area has delicious fare made from the meat of these ocean-dwellers.

But conchs are not the only signature dish to try. For those with a sweet tooth, the delicious confections at The Key Lime Pie Lady are unmissable. Made from native key limes, these award-winning pies have been praised by food critics across the country.

You might also like: First-time Florida Keys: island hopping along the Overseas Highway

A blonde woman in a green blouse smiles as she stands next to her painting, a large watercolor canvas depicting a large colorful lionfish
Local artist Michelle Nicole Lowe poses by her painting of a lionfish entitled 'Invader' © Michelle Lowe

Local art

Islamorada’s lush green foliage and ever-changing marine life offer plenty to wonder over. The colorful surroundings have attracted a vibrant community of artists who draw inspiration from the striking natural surroundings. Local artist Michelle Lowe’s love of the tropics fuels her creative process. At her gallery near the Overseas Highway, Lowe displays beautiful watercolors and prints of various flora and fauna she has observed throughout south Florida.

Just beyond Lowe’s gallery is another hub of creativity. The Morada Way Arts and Cultural District, a spirited six-block stretch of downtown, is rife with galleries, working studios, and even a Little Free Library tucked down a side street. Every month, the organization hosts an ‘Arts Walk’ that brings the area to life with live music, special vendors and plenty of artistry to marvel at.

And it’s not just the visual arts that flourish in Islamorada. The ICE at Founders Park and the Coral Shores Performing Arts Center present an impressive roster of live shows and performances throughout the year. Fans of live music should head to the Lorelei for a laid-back vibe and oceanfront views. You may even catch a peek of the ‘Nautilimo’, a pink ocean-going Cadillac, in the neighboring marina.

Three people are silhouettes against a vivid sunset as they stand and sit in a rowing boat. One of them holds a fishing rod
Fly fishing is a quintessential Florida Keys pastime © Danita Delimont / Getty Images

Sportfishing capital

Islamorada’s location between Florida Bay and the Atlantic Ocean provides an outstanding diversity of fishing options, from backcountry sport and fly fishing to deep-sea. It’s no surprise, then, that many celebrated anglers call Islamorada home. This includes Sandy Moret, world-class fishing guide and founder of the Florida Keys Fly Fishing School. If Moret isn’t on the water, chances are he’s at his store, Florida Keys Outfitters. The lucky customer might even find themselves privy to some insightful advice from the expert fisherman.

Thanks to the Florida Keys National Marine Sanctuary, much of the marine life and reefs off the town's coast remain intact and protected. Alligator Reef, a Sanctuary Preservation Area, is one of the best places to dive or snorkel around the Keys. Bustling with marine life, the reef, easily identified by Alligator Lighthouse, boasts one of the greatest variety of fish species in the world.

An aerial view of crystal blue waters, speckled by small fishing boats, with a rusty lighthouse in the centerview of Alligator Reef © Caitlyn Mentel.jpg
A bird's-eye view of Alligator Reef's boat-speckled waters © Caitlyn Mentel

Lignumvitae Key Botanical State Park, once the private island of a wealthy Miami chemist, provides a fascinating look at what thrives on land. Visitors will see a vast array of native plants including the hardwood hammock tree and the key’s namesake, Lignum vitae, a tree with one of the heaviest woods in the world. Walking around the well-preserved island, it’s hard not to be taken in by the surrounding beauty, one that embodies the ethos of Islamorada itself: a place where time is more of a suggestion than a reality, and where the magic of the natural world is laid bare.

Insider tip: Download the ‘Freebee’ app and call a local shuttle — just like an Uber — at any time. The shuttles are eco-friendly and, better yet, free!

You might also like:

Florida with kids (beyond Disney): the Gulf Coast
Aquatic thrills in coastal Florida
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