Walking Trails in Islamorada

Islamorada is known for its ocean views and easy access to the water, but several trails and green spaces offer opportunities for walking and nature observation. While the elevation remains flat and the trail mileage modest, the local routes highlight the surrounding mangroves, tropical hardwoods, and coastal ecosystems that define the Middle Keys. Exploring on foot offers a slower pace to experience the landscape, especially if you want to take in the natural surroundings away from busier tourist areas.

This guide includes the best places to go hiking in Islamorada and nearby areas: trails and walking routes that are practical for steady movement, photo opportunities, and routine outdoor time.

Located just north of Upper Matecumbe Key, Windley Key Fossil Reef Geological State Park includes a set of short trails built through former quarry land. The park is situated on land once used by the Florida East Coast Railway, and exposed sections of fossilized coral reef can still be seen in the old quarry walls. The Hammock Trail and the Quarry Trail loop through native vegetation, and interpretive signs describe the plants and geological features.

The walking paths are flat, well-maintained, and shaded by canopy. Most visitors complete the trails in under an hour, but many take time to stop and examine the rock formations and native hardwoods. Benches and informational markers are spread throughout the loop. If you are interested in hiking in Islamorada and want a walk that includes education about the region’s geological history, this park provides a clear overview.

Indian Key Historic State Park is accessible only by boat or kayak, but once you arrive, a network of walking paths leads you through the remains of a 19th-century settlement. Located just offshore from Islamorada, the island includes ruins, signage, and trails that loop around the perimeter and connect to shaded interior spaces. The layout is informal, with packed sand and coral paths that guide you through open areas and overgrown ruins.

This hike offers views of the surrounding water and plenty of open space. The walk is not long, but you’ll likely explore side paths and pause at remaining foundations and markers. The terrain is easy to manage and gives you a sense of scale for how people once lived on this small island. The hike is most rewarding for those who want a walk combined with a historical perspective.

Long Key State Park is a short drive south of Islamorada and includes the Golden Orb Trail, a 1.1-mile loop through mangrove forests and coastal habitats. The trail begins at the main parking area and provides boardwalk sections, observation points, and shaded spots with signage identifying local plants and bird species. The route connects to the shoreline, offering occasional access to water views and resting places.

The trail's surface is a mix of hard-packed ground and elevated platforms. It stays dry and accessible throughout the year. This is one of the more developed hiking trails in the Middle Keys and gives visitors a chance to walk through multiple ecosystems in a short span. The park also includes picnic areas, which make it easy to extend your visit beyond the trail.

Lignumvitae Key Botanical State Park is only accessible by private boat or charter, but once on the island, a small trail system leads visitors through a preserved hardwood hammock. Guided tours are sometimes available, but you can also explore the paths on your own. The island features native plants that are less common in other parts of the Keys due to development and environmental changes.

The hiking trail loops past the historic Matheson House, the only structure remaining from early settlement activity on the island. The walk includes dense shade and minimal elevation change, and it can be completed in under 45 minutes. Hiking here gives you access to one of the region's last intact examples of this unique habitat type.

Located on Lower Matecumbe Key, Anne's Beach includes a long boardwalk that runs parallel to the coastline with intermittent beach access points. Though not a trail in the traditional sense, the elevated walkway provides steady space for walking alongside mangroves and clear views of the Atlantic. The whole stretch connects two parking areas and includes shaded pavilions and benches.

This is one of the more relaxed places to walk in Islamorada, especially if you want consistent ocean views without obstacles or large crowds. The entire boardwalk can be covered in under 30 minutes, but many visitors spend more time stopping at the different points. It’s a good choice for early morning or late afternoon movement near the water.

Located 30 minutes north of Islamorada, Key Largo Hammock Botanical State Park includes the 1.6-mile Port Bougainville Trail. This path leads through a protected hardwood hammock and includes shaded sections, signage, and the remains of a development project halted in the 1980s. The route offers a sense of isolation, even though it's close to developed areas.

The trail is well-marked and loops through quiet areas that support birdwatching and observation of native plant life. This is one of the best places near Islamorada for a longer, shaded walk with minimal elevation change but a consistent hiking feel. It's a practical choice for those who want time on a managed trail system with few interruptions.

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