THIS COLORFUL VILLAGE IN THE FLORIDA KEYS IS THE ULTIMATE ISLAND ESCAPE

The Florida Keys are about as magical a vacation destination as there ever was. The archipelago composed of hundreds of tiny islands, most of which are uninhabited, is located just off Florida’s southernmost point and is connected to the mainland via the 113-mile Overseas Highway. While making the full trek from Key Largo to Key West is a bucket-list trip worth planning significant time around, if you’ve only got a long weekend, Islamorada is the place to be.

The colorful waterfront village encompasses six islands strung between Key Largo and Key West. Known as the Sportfishing Capital of the World, there’s plenty more to do here than sit and stare into the mesmerizing turquoise expanse, though the water’s bewitching blue-green certainly makes it easy. Whether you want to shop for beach-inspired art, snorkel in the sea, or sip on a pina colada while watching the most spectacular sunset of your life, Islamorada is the place to be. Here are the 20 best things to do in Islamorada, Florida.

Learn About The Area

Visit the History of Diving Museum

If you’ve ever wondered about the entire other world that exists under the sea, the History of Diving Museum can provide some of the answers to your most burning questions. Open since 2005, the museum features one of the world’s largest collections of diving helmets, air pumps, and armored suits that were historically used to dive into the depths of the ocean.

Spend Time at the Florida Keys History & Discovery Center

This local history museum tells the story of the Florida Keys, from its first inhabitants to common day. Exhibits tackle a range of subject matter from the building of the Oversea Railway to the incredible coral reef system that exists all around the Keys.

Traverse the Trails at Windley Key Fossil Reef Geological State Park

Walk through a preserved quarry that was once used to produce a decorative stone called Keystone and build the Overseas Railroad. At Windley Key, walking trails take visitors through hardwood hammock forests and to see ancient coral trapped inside 8-foot-high quarry walls. For more information on the historic site, head to the visitors center for educational exhibits.

Relax On The Beach

Watch Windsurfers at Anne’s Beach

This public beach located at mile marker 73.5 is a popular spot for windsurfers to catch the breeze and ride the flat, placid waters. Pick a sandy spot in the shade, and settle in for a relaxing day in the sun. Restrooms, pavilions, and a 1,300-foot boardwalk winding through mangroves are all part of the appeal.

Explore Indian Key Historic State Park

Accessible only by kayak, this tiny remote island was once the county seat for Dade County. Today, you can paddle right up to shore (try Robbie’s Marina or Backcountry Cowboys for rentals), then spend the day hiking, swimming, and sunbathing in peace.

Bring the Family to Founders Park

This 45-acre park is the ultimate place to bring the entire family. With a shallow-water swimming area on the Florida Bay, grills, pavilions, picnic tables, and tiki huts, there’s everything you could need (and more) for the ideal beach day. Other park amenities include an Olympic-sized pool, a splash pad, and sports fields.

Have Fun On The Water

Go Kayaking or Paddle Boarding

One of the best ways to take advantage of the Islamorada’s best feature is by paddling through it. There are plenty of places to rent a watercraft, but one of the most popular is the Kayak Shack at Robbie’s Marina. If you don’t want to set out on your own, the Shack offers guided tours to Indian Key State Park, a mangrove canopy system, or Lignumvitae Key Botanical State Park.

Cast Your Line

It’d be a shame to visit the Sportfishing Capital of the World and not reel in a big catch. Islamorada is home to dozens of fishing charters that will be more than happy to take you out for a day or half-day on the water. Try DirtyBoat Charters or Skins and Fins Charters.

Swim with Dolphins at Theater of the Sea

It’s easy to up close and personal with sea life in Islamorada, but swimming with dolphins might take a bit more preparation than just diving into the deep blue. At Theater of the Sea marine mammal park, admission comes with dolphin, sea lion, and parrot shows, plus a bottomless boat ride, fish and reptile tour, and access to a lagoon-style beach. Visitors can add on a special dolphin swim for a once-in-a-lifetime experience.

Visit Robbie’s Marina of Islamorada

This legendary Florida Keys spot is a hub for all things island-themed fun. Feed the famous giant tarpon right off the docks, hop aboard Captain Michael’s party fishing boat, or take a snorkeling tour. If you prefer to stay on land, snag a seat at Hungry Tarpon Restaurant where you can dine with a view of the water from sunup to sundown.

Check Out the Local Arts Scene

Visit Rain Barrel Village

Another iconic Keys spot, folks have been flocking to Rain Barrel Village to take a picture with Betsy the Lobster, stroll through lush gardens, and buy local art for the past 40-plus years. Just walking through the colorful galleries and open-air shops of this tropical oasis is enough to put you on island time. The cocktails and live music at the onsite bar only add to the festivities.

Wander the Morada Way Arts & Cultural District

This six-block corridor along Morada Way is essentially the Florida Keys’s downtown or main street. The lively district is home to dozens of local galleries, restaurants, studios, and shops surrounded by parks and bike paths. Spend an afternoon popping in and out of stores where you’ll find one-of-a-kind treasures at every turn.

Find A New Favorite Restaurant

Indulge in a Seafood Buffet

All-you-can-eat shrimp is a novelty experience of all great beach vacations, but you can take things to the next level at Whale Harbor Seafood Buffet, where there are more than 60 different items to choose from. The raw bar is stocked with the freshest crab legs, oysters on the half-shell, and peel-and-eat shrimp.

Try the Local Delicacy

Everyone knows the Florida Keys are famous for key lime pie. If you want a slice of the tart-sweet dessert, head to Blond Giraffe Key Lime Pie Factory. Grab a table in their Serenity Garden and enjoy your treat. Get it frozen and chocolate covered if you’re feeling bold.

Take a Coffee Break

The brightly colored Midway Café and Coffee Bar is one of the best places to grab breakfast in Islamorada. If you don’t visit for your morning meal, take a peak into their well-stocked pastry case and order from a long list of specialty coffee and tea drinks like an Almond Joy (coconut, chocolate, almond latte) or Banana Chai Frappe.

Enjoy Authentic Mexican Cuisine

Bad Boy Burrito doesn’t mess around when it comes to serving up the best overstuffed burritos you can find just about anywhere. Get yours filled with Key West pink shrimp, pork carnitas, or local fish, then choose from five different homemade sauces, and all the toppings. They also have one of the best brunches in town.

Sample Craft Beer

Is there anything better than an ice-cold brew on a hot day? The Sandbar Sunday, an American Wheat Ale at Islamorada Beer Company was made for days spent on the water. Saddle up to the bar at their Islamorada brewery for a pint, or a flight that might include other refreshing libations like the Keylime Hibiscus Ale or the Floridays Tropical Pale Ale.

Have a Nice Dinner Out

There’s not a more romantic spot in all of Islamorada than the dining room or spacious veranda of Pierre’s Restaurant in Morada Bay. Make a reservation for this upscale but relaxed restaurant housed in a two-story West African-style Old Colonial home. Dine on dishes that run the gamut from traditional French cuisine to fusion creations. For example, a classic Roasted Poulet Rouge gets gussied up with black truffle jus and Mallard Duck Breast is served with an Italian chestnut puree and maple.

Book a Beautiful Stay

Find Paradise at The Moorings Village

Find yourself surrounded by swaying palm trees and other tropical flora in the tranquil Moorings Village compound. You’ll be able to stroll to the water from the comfort of a private cottage. Complimentary kayak and standup paddle board rentals add to the fun.

Have it All at the Islamorada Resort Collection

Think of this stay as a three-in-one deal. The Islamorada Resort Collection has two properties—Amara Cay Resort and La Siesta Resort & Villas—and a third, Three Waters Resort & Marina, on the way in fall 2024. Staying at one resort gives you access to amenities, restaurants, and beach access at all of them. This includes a dock with wet slips, free parking, beach and pool umbrellas, bikes, paddleboards, kayaks, a complimentary shuttle within a four-mile radius, and more.

Unwind in a Luxurious Suite at Cheeca Lodge & Spa

This oceanfront resort is known for its casual elegance and wide array of amenities. Choose from five different dining options, wander 27 acres of lush gardens, relax on a private beach, play the 9-hole golf course, or cast a line off the longest fishing pier in the Florida Keys.

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2023-11-17T15:58:13Z dg43tfdfdgfd