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I’ve Been Visiting the Florida Keys for 36 Years—and This Tiny Village Is the Place I Keep Going Back to Stay at Pines & Palms Resort, a boutique hideaway where you can sip your morning coffee in a hammock steps from the water and catch a sunset on the dock. Grab a seat at Square Grouper, where illicit Florida Keys history blends with the freshest seafood and stellar sunset views.

Wander through the Morada Way Arts & Cultural District, home to working studios, galleries, and monthly art walks that reflect the town's creative soul. Hop on a boat or kayak and explore the area's coral reefs and snorkeling trails. Visit the History of Diving Museum, where 16th-century treasure chests and vintage diving helmets tell the story of humankind’s love affair with the sea.

Roughly 85 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.

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, [and] respectful.” A fixture in the community for the past 20 years, Pantaleo helped build the creative spirit that pulses through the village, from the vibrant art galleries and studios dotting the streets to gallery nights with live music. I’ve returned again and again to this stretch of islands—I love the energy of Key West and the saltiness of Marathon and Key Largo, plus there's plenty to do up and down the Florida Keys.

Still, as a longtime Floridian, Islamorada has a piece of my heart. Here's everything you need to know to plan the perfect trip. Best Hotels & Resorts Pines & Palms Resort A cluster of cozy oceanfront cottages dating back to the 1930s, Pines & Palms Resort received a stylish refresh thanks to HGTV’s Bryan and Sarah Baeumler in 2025. 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 at the property's beachside tiki bar and pier, play a round on the Jack Nicklaus–designed nine-hole 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.

With three pools and spacious accommodations including oceanfront suites and private casitas, Cheeca Lodge & Spa is equally suited to romantic escapes and family getaways. Islander Resort Set on 24 tranquil acres in the heart of Islamorada, Islander Resort combines vintage charm with recent updates. The property’s 114 rooms and suites 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 Get outside 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. The 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.” The third Thursday of each month brings 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 real bar of silver. 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 Indigenous 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.” Advertisement 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 store 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 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 since 1978.

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 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 Restaurant & Cabana Bar 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 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 bird's-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, 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.

The community comes alive during Island Fest, held in late March or early April at Founders Park, a scenic waterfront gathering space with a beach, marina, and amphitheater, among other amenities. The two-day celebration features art shows, a car rally, sandcastle contests, live music, and cooking contests where local chefs compete dish to dish. September to November is the quietest time to visit, but it’s also peak hurricane season. Plan accordingly and always check forecasts during this time of year, as the season is officially from June through November.

How to Get There Islamorada is about a 90-minute drive from both Miami International Airport (MIA) and Key West International Airport (EYW), making it easily accessible from either direction along the 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 fully explore Islamorada is by car, though much of it is easily navigable on foot or by bicycle. Some hotels and resorts, including Pines & Palms, offer complimentary bikes. You can also rent one 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. Riders simply request a pickup via the app, and a local electric vehicle will arrive. It typically operates from 7 a.m. to 12 a.m. 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.

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