Craving crystal waters, island flavors and relaxation? Islamorada serves it all
If you’re dreaming of a summer escape to the Florida Keys — Islamorada, a village of islands nestled between Key Largo and Marathon and a scenic 90-minute drive from Miami — should top your vacation bucket list.
Known as the sportfishing capital of the world, Islamorada offers far more than rods and reels. There are unique adventures that include painting alongside a sea lion, swimming with dolphins, and hand-feeding giant tarpon. Art enthusiasts will appreciate the island’s monthly art walk, and Islamorada has bragging rights to chef-driven restaurants and locally brewed beers that hit just right after a day on the water. For those looking to unwind, a new luxury resort delivers island vibes and ultimate seclusion — perfect for soaking in serenity.
This Islamorada resort is a hidden sanctuary
Best for: family vacations, group celebrations, romantic retreats, dog-friendly
For those who prefer the luxury of space and privacy over a typical resort, The Islands of Islamorada is a new oceanfront haven with a collection of 22 villas and eight one-bedroom suites tucked in a gated community on a quiet stretch of Old Highway. A feeling of serenity and exclusivity washes over you the moment you pull into the lush drive and the gates close behind you.
Staying here feels like having your own private townhouse, and even at full occupancy, the lush grounds never feel crowded. Each spacious, three-story villa features four generous bedrooms, a fully equipped kitchen, inviting living and dining areas, tranquil balconies, and private outdoor spaces designed for relaxation. There are even special touches left for guests like coffee that’s made in the Florida Keys, along with everything you need from towels to dishes.
Set along a private stretch of pristine beach, the resort revolves around its most stunning feature: the shallow, crystal-clear water. The property is brimming with amenities designed for both adventure and relaxation. Unwind at one of two waterfront pools, or head out on complimentary kayaks, paddleboards, or a Hobie Cat sailboat. You may even spot an array of fish and sea turtles darting through the water. Play a game of pickleball, fish, or enjoy guilt-free golfing from the driving range on the shore, smashing biodegradable golf balls (fish food) into the water. As evening sets in, grab a front-row seat by the water to catch the sunset, then cozy up under twinkling café lights with a s’mores kit in hand, perfect for roasting around the resort’s firepit.
Savor the flavors of the ‘Key Lime Culinary Trail’
Key lime is a signature flavor of the Florida Keys, and The Islands of Islamorada celebrates the citrus fruit with their own curated “Key Lime Culinary Trail.” Resort guests can hop on complimentary bikes and follow a mapped route highlighting Islamorada’s most delicious key lime — inspired bites and sips, all within an easy three-mile radius of the property. Start your day with a key lime pie frappe at Midway Café, then head to Lazy Days for fresh-caught fish coated in Japanese breadcrumbs and topped with a key lime butter sauce. Cool off with a scoop of key lime pie ice cream from family-owned Keys Chocolate & Ice Cream, and cap it all off with a boozy key lime colada at Lorelei Restaurant & Cabana Bar, a lively waterfront spot that’s especially magical at sunset.
If you want the best key lime pie on the island, drop in The Trading Post grocery store to grab one of The Key Lime Pie Lady’s made-from-scratch pies. While it may not look fancy, this is one of the best Key lime pies you’ll ever taste, with just the right balance of sweet and tartness and a flaky graham cracker crust.
Boating and fishing are epic adventures in Islamorada
Islamorada is famed for its world-class fishing, scenic sandbars and fiery sunsets, and the concierge team at The Islands of Islamorada will arrange a custom charter that departs right from the resort’s private marina. One of the top choices is a private sunset cruise with Cheeca Rocks Charters, helmed by the knowledgeable Capt. Rob Reiner. You’ll meander through peaceful canals lined with waterfront homes and mangroves, on the lookout for wildlife like dolphins, manatees, and even the occasional crocodile. As the sun begins to set, the boat will anchor in a perfect spot to take in the dramatic colors. To top it off, the captain can drop you at one of his favorite waterfront restaurants for dinner — from there, call a rideshare back to your resort. Bonus: well-behaved dogs are welcome on board, making it a memorable outing for furry companions too.
Top dining in Islamorada
Islamorada has bragging rights to some of the best dining in the Florida Keys. Those in the know line up outside the doors of the Square Grouper restaurant before 4 p.m. to be the first in line to grab a window table or seat at the bar of the third-floor Sunset Lounge. While the main restaurant opens at 5 p.m., the adults-only upstairs lounge opens at 4:20 p.m. for their epic “Stoned Happy Hour” that runs through 6 p.m. from Wednesdays to Sundays. The lounge’s sky-high perch and oversized windows showcase incredible Gulf views — you may spot manatees or dolphins playing in the marina below — so you’ll want to get there early to snag a prime spot before sunset.
The other major perk is their amazing seafood deals, like $5 stone crabs (when in season from May to October), $2 blue point oysters and 20% off drinks. Don’t skip regular menu highlights like the crispy conch that’s served on warm, soft steamed buns, and the wildly flavorful wahoo tataki.
If you’re looking for an upscale dining experience or a place to celebrate a special occasion, Chef Michael’s is an institution that never misses. Only open for dinner, their creative seafood-centric menu stars locally loved favorites such as beautifully prepared ceviche served in a coconut shell, conch and shrimp fritters, and any of their fresh fish preparations and specialties. Reservations are suggested.
Papa Joe’s Waterfront — a recent reincarnation of its original 1938 location — flaunts a stunning waterfront perch that also begs a sunset celebration. Families and groups of friends will enjoy congregating on the lawn to play games, while adults flock to the upstairs tiki bar to sip something tropical and watch the sun dip into the horizon. The locals come there for their delicious burgers and the smell from the grill will hit you upon arrival.
Don’t miss these other standout spots: Ziggie & Mad Dog’s, a legendary steakhouse; Bayside Gourmet, a cozy, family-owned gem offering everything from deli favorites to fresh-baked goods and pizza; and Island Grill, where the waterfront views are as memorable as their famous tuna nachos. And when it comes to the best coffee and pastries served in a dreamy environment, search out Café Moka, hidden away in the lush Village Square.
Paint with a sea lion at Theater of The Sea
While the Theater of The Sea is one of the oldest marine mammal facilities in the world and has been family owned since 1946 — there are always new things to do at the tropical park. Time your visit around educational programs centered around the sea turtles, rays and birds that inhabit the lagoons; grab a seat to watch theatrical performances by the resident dolphins and their trainers; and ride their bottomless boat to see the dolphins play in the water.
Animal lovers will enjoy interactive experiences like swimming with the dolphins, sea lions and sharks — but if you want an activity that sparks pure joy, book a class to paint with their resident sea lion, Bella (who they rescued and rehabilitated and can’t be returned to the ocean). Bella has a neurological disorder, and the team uses enrichment exercises like painting to keep her happy and centered. After picking out your preferred paint colors, you’ll hold the canvas as Bella creates her masterpiece by holding a brush in her mouth (watching her concentrate is the most adorable thing you’ll ever see). You’ll leave with a custom piece of art, and maybe even a kiss from Bella. The experience is $115, but it also includes your park entrance fee.
More must-do activities in Islamorada
Whether you’re a first-timer or regular visitor to Islamorada, don’t miss a stop at Robbie’s Marina to hand feed the enormous tarpon right from the dock. Simply buy some bait, hold it over the water, and get ready for a heart-pounding moment as the massive silvery fish leap up to grab their snack — cue the giddy screams, laughter, and plenty of photos.
If you’re a craft beer enthusiast, drop by the neon-yellow Islamorada Brewery and Distillery for one of their beers on tap or a specialty cocktail. Their spacious beer garden is a welcoming hangout spot for friends, family — and even your pup. Florida Keys Brewing Co. is another locally owned microbrewery worthy of a stop to sample a flight of beers that range from favorites to seasonal drops, and to hang out in their beautiful beer garden to play some games or attend one of their many events.
And if you’re into vibrant island art, mark your calendars for the monthly Morada Way Art Walk, held on the third Thursday of every month. During this well-attended evening event, local galleries keep their doors open late, and the street comes alive with food vendors, artisan booths, and live music.
