Islamorada Serves Up All the Florida Keys Charm Without the Crowds

Roughly 80 miles south of Miami and 80 miles north of Key West, Islamorada offers the perfect blend of Old Florida charm and salty barefoot luxury—no high-rises, no big-box stores, just freshly caught fish, breezy galleries, and the healing rhythm of the sea. With 18 miles of shoreline stretching across six islands, this historic village in the Upper Florida Keys invites visitors to slow down and let the water set the pace.

I’ve returned again and again to this stretch of islands—I love the energy of Key West, the saltiness of Marathon and Key Largo, and there’s plenty to do up and down the Florida Keys. Still, as a longtime Floridian, Islamorada has a piece of my heart.

For local artist Roberto “Pasta” Pantaleo, who founded the Morada Way Arts & Cultural District, the pull of Islamorada runs deep. “I came to South Florida from Brooklyn in 1970 when I was 12,” says Pantaleo. “I knew I needed to be near water. When I found Islamorada, the topography here and the people fit me like a glove. I kept coming back until, eventually, I never left. It just felt like home. The people here are kind, nature-driven, respectful.” A fixture in the community for the past 20 years, Pantaleo helped build the creative spirit that pulses through the village, from gallery nights with live music to the vibrant art galleries and studios dotting the streets.

Best Hotels & Resorts 

Pines & Palms Resort

A cluster of cozy oceanfront cottages dating back to the 1930s, Pines & Palms Resort just got a stylish refresh thanks to HGTV’s Bryan and Sarah Baeumler. Guests will find a true mom-and-pop feel with renovated interiors, a poolside tiki bar, breezy porches, and an on-site boutique with local artwork and handmade goods. On the days I wanted to explore beyond the resort, I grabbed one of the complimentary bicycles to poke around the quaint little downtown filled with shops and galleries less than a mile away.

Cheeca Lodge & Spa

This resort delivers luxury across 27 oceanfront acres. Guests can unwind in the Cheeca Lodge & Spa‘s spacious suites or private casitas, enjoy a round on the Jack Nicklaus–designed golf course, or relax with a spa treatment. Don’t miss dinner at Atlantic’s Edge, where freshly caught fish often stars on the menu. From its three pools to beachside tiki bar and pier, Cheeca is equally suited to romantic escapes and family getaways, especially with its new oceanfront suites offering unbeatable sunrise views.

Islander Resort

Set on 24 tranquil acres in the heart of Islamorada, Islander Resort combines vintage charm with fresh updates. The property’s 114 bungalows and 25 townhome-style villas surround two sparkling pools and a shady grove of hammocks. Amenities include a putting green, pickleball courts, and a revitalized saltwater pool terrace. It’s a relaxed, family-friendly hideaway with plenty of space to explore—ideal for travelers who want a taste of local history alongside a modern island escape.

Best Things to Do

Go out with Bamboo Charters.

Bamboo Charters offers a family-friendly experience on the water, with fishing, snorkeling, sightseeing, and cruising options. Owner Matt Bellinger, a longtime Florida Keys resident, combines his deep knowledge of marine biology with a strong commitment to eco-friendly tours. “You won’t find any grumpy guides here—just a welcoming, family-run experience,” says Pantaleo. Travel + Leisure senior editorial director Nina Ruggiero took her dad out with Bamboo Charters on a father-daughter fishing trip to the Florida Keys—Bellinger cleaned and filleted the day’s bounty, readying it for dinner at the Hungry Tarpon Restaurant, where they’d cook their catch.

Discover the Morada Way Arts & Cultural District.

Morada Way Arts & Cultural District is the only true “Main Street” between Key West and Miami, and one of the most vibrant enclaves in the Upper Keys. What started as a quiet corner and a single gallery has blossomed into a dynamic six-block neighborhood of studios, shops, restaurants, and live music venues. “It used to be a car-and-bar town,” says Pantaleo. “Now, people can stroll at night, listen to music, and hang out with a glass of wine.” Third Thursdays bring the festive Art Walk, when the district bursts with local art, live music, and technicolor vibes.

Dive into the past at the History of Diving Museum.

Encircled by a vivid undersea mural, the History of Diving Museum showcases thousands of artifacts tracing 4,000 years of underwater exploration. Exhibits include antique dive suits, treasure-hunting tools, and pioneering scuba gear. Don’t miss the “Parade of Nations” helmet collection or the treasure room where you can lift a silver bar.

Feed the tarpon at Robbie’s.

No trip to the Keys is complete without a stop at Robbie’s, located on the edge of Lower Matecumbe Key.  Equal parts outdoor market, marine adventure hub, and ramshackle hangout, this lively waterfront compound is home to the Hungry Tarpon Restaurant, eclectic souvenir stands, art vendors, and one of the area’s most memorable experiences: feeding massive tarpon that leap out of the water for bait. “It’s kind of a bizarre zoo that stays packed,” says Pantaleo. “Everybody knows Robbie’s—it’s world-famous for a reason.”

Explore the Florida Keys History & Discovery Center.

Tucked inside the Islander Resort, the Florida Keys History & Discovery Center is a state-of-the-art facility that brings the region’s complex past to life through exhibits on First Nations peoples, Spanish treasure fleets, Henry Flagler’s railway, and the 1935 Labor Day hurricane. Upstairs, visitors can catch documentaries in a 35-seat theater and explore rotating exhibits. “It was made possible through the preservation efforts of people down here years ago,” says Pantaleo. “It’s a beautiful space with real depth, and it kind of kicks off the whole art district.”

Best Shopping

World Wide Sportsman & Bass Pro Shops

Located bayside, World Wide Sportsman, now part of Bass Pro Shops, is a paradise for anglers and outdoor enthusiasts. This massive outfitter stocks everything from rods and reels to technical fishing gear and resort wear. “It’s a mecca for sportsmen,” says Pantaleo. “There’s a working marina, charter guides, a full-service dock, and the best outfitter store in the Keys.”

Rain Barrel Village

No visit to Islamorada is complete without a stop to see Betsy, a towering, 30-foot-tall, 40-foot-long spiny lobster sculpture that’s become one of the most photographed roadside attractions in the Florida Keys. Behind her, a cluster of pastel shanties houses Rain Barrel Village, an open-air market and artist haven for more than 40 years. Stroll under tangled garlands of buoys and past glassblowers shaping octopi in real-time, and browse everything from handmade ceramics to local paintings, textiles, and nautical tchotchkes.

Best Restaurants

Lazy Days

Perched right on the water, Lazy Days delivers laid-back Keys dining with one of the best sunset views around. The vibe is quintessential beach bar, but the food is surprisingly refined—especially when it comes to the day’s fresh catch. Ask for it “Lazy Style” (topped with tomatoes, scallions, mushrooms, garlic, and Key lime butter), or bring your own and let them do the cooking. Sit out on the breezy deck, order a cold beer, and watch the sun drop below the horizon—it’s peak Florida Keys.

Lorelei Restaurant & Cabana Bar

Just off the Overseas Highway, marked by a massive mermaid statue, Lorelei is a classic Florida Keys watering hole—equal parts tiki bar, family restaurant, sunset lookout, and low-key music venue. “This is where everyone hangs out: fishing guides, locals, even a president or two,” says Pantaleo. The crowd at golden hour buzzes with frozen drinks in hand—I ordered the Key lime colada, its graham cracker rim catching the last of the sun—while local bands and magicians entertain from the dockside stage.

Chef Michael’s

Tucked into a cottage in the Morada Way Arts & Cultural District with the sign “Peace, Love & Hogfish,” Chef Michael’s serves some of the freshest, most carefully sourced seafood in Islamorada—and it takes “know your fisherman” to another level. From the house hogfish “Juliette,” seared with scallops, shrimp, and chardonnay butter, to rotating selections of lionfish, snowy grouper, and yellowtail, the menu is rooted in quality and creativity.

Square Grouper Islamorada

A sly nod to the smuggling slang of the 1970s, Square Grouper blends Keys history with high-end coastal cuisine. Housed in a stunning space just off the marina, the restaurant features jellyfish-like chandeliers, panoramic sunset views, and art-covered walls. I grabbed a table upstairs with a birds-eye view, cocktail in hand, and devoured snapper ceviche with bright citrus and a touch of heat. I followed with the flash-fried conch beloved by regulars like commercial fisherwoman Rachel Bowman. Get there by 4:20 (another cheeky reference) and experience the freshest fish, free spirits, and a front-row seat to the good life. No reservations needed.

Best Time to Visit

For a blend of breezy weather and thinner crowds,, late spring is the sweet spot to visit. April brings sunshine and warm waters without the oppressive heat of summer or the high-season crowds of winter. It’s also when the community comes alive with Island Fest at Founders Park, a two-day celebration featuring art shows, a car rally, sandcastle contests, live music, and the beloved Taste of Islamorada, where local chefs compete dish to dish. Founders Park is a scenic, year-round waterfront gathering space, complete with a dog park, beach, marina, amphitheater, and Olympic-sized pool where elite swimmers train.

September to November is the quietest time to visit, but it’s also peak hurricane season. Plan accordingly and always check forecasts during hurricane months.

How to Get There

Islamorada is less than a two-hour drive from both Miami International Airport (MIA) abd Key West International Airport (EYW), making it easily accessible from either direction along the scenic Overseas Highway. Most travelers fly into MIA for the quick drive south, but flying into EYW offers an equally scenic route north through the Lower and Middle Keys. Either way, you’ll want to rent a car. Once in Islamorada, you can bike or walk around town, but a car is essential for exploring nearby beaches, parks, and hidden gems along the archipelago.

How to Get Around

The best way to explore Islamorada is by car, but once you’ve arrived, much of it is easily navigable on foot or by bike. Some hotels and resorts like Pines & Palms offer complimentary bikes, or you can rent from a local shop like Backcountry Cowboy Outfitters, which includes helmets, locks, and baskets. A car is essential for exploring attractions further afield (think: state parks, marinas, or hidden roadside fish shacks).

Freebee offers free, on-demand electric shuttle service within Islamorada and can be booked through the app. Riders simply request a pickup, and a local electric vehicle will arrive. Freebee typically operates from 10 a.m. to 10 p.m., with slightly extended hours during peak season. Uber and Lyft are also widely available in Islamorada and throughout the Keys.

Several shuttle companies, including Keys Shuttle and Florida Keys Express Shuttle, offer reliable daily service between both major airports, as well as destinations throughout the Keys. Private charters are also available for groups.