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Long Weekend: Islamorada, Florida

World-class sportfishing, sea-to-table cuisine, romantic coves, and mesmerizing sunsets? It’s all in a day’s play along this string of enchanting islands.

What To Do

As I wiggle my toes in the sand at Morada Beach Café, the cotton-candy pink sky, a hue I know so well as a Florida native, decides to up-level itself. The Florida Keys are revered for their can’t-look-away sun salutes, yet on this summer eve, the sky delivers a light show so compelling that a local proclaims it as one of the top-10 sunsets he’s ever seen. “And living on Islamorada for 25 years, that’s saying something,” he adds. As unforgettable shades of citrus-orange streak through the clouds, the usual restaurant clatter ceases: Forks are laid to rest, servers stop in their tracks, and diners scurry from their tables to capture iPhone memories. Couples place their arms around each other, kids point upwards, and for a fleeting moment, we are all suspended in time as nature reminds us who’s in charge. I will never forget Islamorada, simply for these few seconds.

The sunsets, though, are only one way to experience this amazing destination’s heavy dose of vitamin sea. Due south of Everglades National Park, Islamorada’s six islands — Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and the offshore islands of Lignumvitae Key — dot the deep-blue waters of the Florida Strait, creating an idyllic ocean playground. Think of it like this: If the Florida Keys were a family, Key West would be the rowdy big sister, Key Largo the smooth-talking uncle, Marathon Key the laidback cousin, and Islamorada the classy patriarch who regales with rum-soaked tales of shipwrecks and fishing. After checking into one of Exclusive Resorts’ brand-new homes at The Islands of Islamorada, I quickly discover how to celebrate the area’s playful DNA, which caters to every type of traveler.

The Adventurist

Considered the sport-fishing capital of the world, Islamorada proudly proclaims a hook ‘em bravado with a culture defined by boats, marinas, and trophy fish. Visit Mangrove Mike’s for breakfast, where your eggs benny overlooks framed photos of revelers displaying their record-breaking catch. Charter a boat to dive deeper into the obsession of sportfishing; local captains ferry visitors out to sea to test their mettle against tarpon, snook, mahi mahi, and the elusive permit. As we embark on “All Lit Up,” a 34-foot Freeman helmed by Captain Kieran “Kiki” Ferrer, a storm has just passed, leaving in its wake a magical sunrise, calm waters, and plenty of wildlife sightings, including dolphins and massive sea turtles. Alas, with three sportfishing newbies trying their hand at casting, we don’t lure in a tarpon, but we do snag a large barracuda and yummy yellowtail, snapping our own photos to show off the catch of the day. Our next stop is the famous Alligator Reef Lighthouse. Named after the USS Alligator that ran aground, the 148-year-old structure is located just four nautical miles offshore and is home to more than 500 species of marine life and pirate shipwrecks. Any visit to Islamorada must also include a boat ride to its famous sandbar, situated less than a mile offshore around Mile Marker 84 on the Atlantic Ocean side. Most weekends, boats of all shapes and sizes pepper the small stretch of sand to party, fish, and soak up the sun.

Islamorada is sprinkled with massive coral reefs so there’s no shortage of exploration for diving and snorkeling adventurers. Memorable sites include the aforementioned Alligator Reef, The Drop (which dips down to 90 feet and is famed for massive rays), and Davey Crocker, an area teeming with sharks, eels, and turtles.

A hook- ’em mentality anchors local culture
The Square Grouper’s famous crab bloody mary

The Family Affair

The Keys are known for many things, but large swaths of sand are surprisingly rare. As the biggest beach in Islamorada, Founders Park Beach is headquarters for family outings. The horseshoe-shaped bay is calm, with Islamorada’s signature coral casting colorful veins of turquoise, green, and deep blue along the water’s surface. Swimming buoys allow for safe, open-water exercise if desired, while the typically mellow currents are a draw for stand-up paddleboarders of all abilities. Storybook palm trees and oversized picnic tables decorate the shore, and beachcombers can spot great blue herons wading among adjacent coves. This is Florida, after all, so you may also spy alligators in the marshy areas (well-marked for safety). Tales of tarpon are the pulse of Islamorada. As such, if you don’t want to brave the deepwater with the kiddos, you’ll still find plenty of action at Robbie’s of Islamorada. Adults can order a bloody mary on the waterfront deck while the whole family takes in the tarpon feeding frenzy. Heroic staff bait the huge “silver kings” and place their hands inside the gaping tarpon mouths, lassoing collective oohs and ahhs from the crowd.

For a more serene experiential escape, float away on a private kayak tour around Bird Island, pack a picnic and head to Anne’s Beach.

The Epicurious

Hogfish, Florida grouper, and shrimp and grits? These Keys-centric dishes celebrate the best of Islamorada and should top the list of any traveling foodie. Your epicurean cheat sheet must also include the Grilled Brie Sandwich with Fried Egg and Raspberry Marmalade at the aforementioned, no-frills Mangrove Mike’s, while lunch or dinner (fish tacos, please!) at The Morada Bay Beach Café & Bar is another necessity. Both the The Lorelei Restaurant and Cabana Bar and Marker 88 (reserve one of the cozy, bayfront cabana tables) stage live music, and lastly, don’t miss the deliciously seasoned peel-and-eat shrimp at the Shrimp Shack or the decadent hogfish at the upscale Chef Michael’s. After a day spent at sea, unwind with a flight of local microbrews at the colorful, reggae-inspired Islamorada Beer Company.

The Historian

History buffs should travel south from Islamorada and learn about the historic railroad running through Pigeon Key, or snap photos of wildlife in the area. Your final item on the bucket-list? Exploring the most famous of the Florida Keys: Key West. Located just 90 miles north of Cuba and lined with pastel-hued, colonial-style homes, Key West is the former stomping grounds of Ernest Hemingway. Follow in his footsteps at the Ernest Hemingway Home and Museum, where the highlight is his famed writing studio. Built in 1862, the West Martello Fort is one of three remaining Civil War-era structures on the island (today, it houses the Key West Garden Club). The Oldest House Museum is exactly as it suggests: Built in 1829 by Captain Francis Watlington, it’s the oldest house on Key West and exhibits historical items from shipwrecks that once made Key West the richest city in America. Finally, order a cocktail and watch the sun dip into the horizon at Mallory Square, one of the world’s most memorable sunset stations. If lucky, you just may witness a sunset as exceptional as the one I experienced on Islamorada. If not? Well, you’ll just have to make a return trip.

Where To Stay


When I pull up to Exclusive Resorts’ new sanctuary at The Islands of Islamorada, I’m immediately captured by the juxtaposition of the whitewashed exteriors against a kaleidoscope of turquoise and deep-green sea. An intimate enclave featuring 22 waterfront vacation villas and eight one-bedroom suites, every bit of this private community is inspired by the gorgeous beachside setting. As my Concierge, Morag, points out all the highlights of my ultra-exclusive weekend escape (state-of-the-art technology, artwork by local photographers, modern décor), it’s soon apparent that the Club is expertly prepared for our “new normal.” In fact, new demands in travel have been Exclusive’s protocol since before the pandemic: With 380+ multi-million dollar residences in its Portfolio, Exclusive Resorts is naturally poised for families who seek the utmost of privacy, upscale accommodations, stellar amenities, and bespoke travel experiences that encompass unforgettable food, adventure, wellness, golf, and more. What’s more, the Club has intentionally kept its Membership small, welcoming just 100 families a year. The result? Pure peacefulness. As I watch yet another beautiful sunset from my master balcony, the stresses of daily life quickly fade. Bubble-gum streaks cast a pink glow across the luxury resort’s private marina and pool, and I’m reminded that, come sun up, tomorrow’s vacation day brings nothing but opportunity.

Residences: 4 | Bedrooms: 4 | Baths: 4.5 | Accommodates: 8-10

Photos courtesy of Stefanie Michejda.