Escape to Islamorada

Islamorada, a scenic village of six islands, includes Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of Indian Key and Lignumvitae Key. 

Known for its eco-tours, watersports of stand-up paddleboarding and kiteboarding, tennis and pickleball, cycling and historic hikes, Islamorada is also called the Sport Fishing Capital of the World because of its stunning angling diversity. Here, backcountry sport fishing and saltwater fly fishing were pioneered. 

Beautiful Islamorada is also acclaimed for its artistic culture, sophisticated galleries, fine dining and boutiques that carry unique gifts and clothing. Overall, it offers an unparalleled blend of satisfying activities and opportunities for downtime. 

Escape to Serenity: Lying at the southern end of Lower Matecumbe Key, the tiny Anne’s Beach park, with clear shallow water, is just off the Florida Keys Overseas Highway at mile marker 73.5 oceanfront. Stretching from Calusa Cove Marina on its northern end to Channel 2 at its southern tip, it features 10 elevated shade structures, six pavilions, a restroom, outdoor shower, free parking and an accessible 1,300-foot-long boardwalk. A great spot for sun-splashed waterfront relaxation, Anne’s Beach was featured in the original Netflix series “Bloodline.” islamorada.fl.us

Escape on the Water: Captain Samantha “Sam” Zeher operates KeyZ Charters, an eco-tour charter specializing in wildlife tours. Her 21-foot tri-hull deck boat is capable of carrying six passengers and cruising in Keys waters as shallow as two feet. Trips includes sightseeing excursions with birdwatching, snorkeling, sandbar tours and sunset viewing. Captain Sam also offers island trips to explore Indian Key, Lignumvitae Key and Alligator Lighthouse — each with a history dating back to the 1800s. keyzcharters.com

Escape into Renewal: The Morada Way Arts & Cultural District is an artistic, inspirational escape through a walkable creative community of Keys artists and makers. Its monthly Third Thursday Art Walk showcases fine arts, paintings, interior décor, music, culinary delights and craft brews to quench thirsts in the creative heart of Islamorada. Exploring the district is an enjoyable way to stimulate the senses and awaken personal creativity. moradaway.org

Escape into Nature: A hike through the 320-acre Windley Key Fossil Reef Geological State Park, a Florida-designated geological site, is a step back in time to see and touch eight-foot-high quarry walls of ancient coral, mysterious hardwood hammock and mangrove fringe trees — and to view migrant birds stopping to rest or feed along their flight path. During construction of the Florida Keys Over-Sea Railroad, Henry Flagler utilized limestone rock from this quarry to raise the road beds and for fill. floridastateparks.org/WindleyKey

Escape to a Hidden Haven: Accessible by kayak, the remote 11-acre Indian Key Historic State Park is located off mile marker 78.5 in Islamorada and was once home to the Keys’ second-largest community. Indian Key was developed by wrecker John Jacob Housman as the site of a lucrative business salvaging cargo from shipwrecks in the 1800s. The island became the first county seat for Dade County in 1836, with 40 houses, a general store, bar, post office, warehouse and the Tropical Hotel. Adventurers can kayak to the island, hike and explore history, picnic, sunbathe, swim and snorkel. floridastateparks.org/IndianKey

Islamorada is where backcountry sport fishing and saltwater fly fishing were pioneered. Photo: Andy Newman

Islamorada is where backcountry sport fishing and saltwater fly fishing were pioneered. Photo: Andy Newman

The oceanfront linear park at Anne's Beach features elevated shade structures along its 1,300-foot-long boardwalk. Photo: JoNell Modys

The oceanfront linear park at Anne's Beach features elevated shade structures along its 1,300-foot-long boardwalk. Photo: JoNell Modys

Step back in time at Windley Key to see and touch eight-foot-high quarry walls of ancient coral. Photo: JoNell Modys

Step back in time at Windley Key to see and touch eight-foot-high quarry walls of ancient coral. Photo: JoNell Modys

This article was updated on April 26, 2024 at 2:28 PM
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