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Monroe County

Florida Keys Wilderness

The best city hikes and walks in Florida Keys Wilderness

4.8

(26)

896

hikers

50

hikes

Urban hiking trails in Florida Keys Wilderness offer a unique experience through distinct ecosystems. The region is characterized by mostly flat terrain, featuring tropical hardwood hammocks, pine rocklands, and extensive mangrove forests. These paths provide opportunities to observe diverse flora and fauna within an urbanized coastal environment. The landscape is generally low-lying, with minimal elevation changes.

Best urban hiking trails in Florida Keys Wilderness

  • The most popular urban hiking route is Fort Zachary Taylor State Park – Southernmost Point Buoy…

Last updated: May 13, 2026

5.0

(1)

24

hikers

#1.

Fort Zachary Taylor State Park – Southernmost Point Buoy loop from Key West

9.80km

02:28

10m

10m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Bear S.
October 27, 2025, The Ernest Hemingway Home and Museum

A must-see in Key West.

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TW lived in Key West for about 30 years.

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Kerstin
October 16, 2025, Southernmost Point

Spectacular sunrise!

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The Key West Shipwreck Treasure Museum houses a 20-meter-high observation tower offering views of the city and the ocean. The observation tower is part of the Key West Shipwreck Treasure Museum, which celebrates the city's maritime history. Visitors can learn about the dangers of shipwrecks and the salvage industry that once made Key West prosperous.

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Bloggmaus
July 16, 2025, Duval Street

Duval Street is a bustling street in the heart of Key West, Florida. It is known for its lively atmosphere, numerous restaurants, bars, shops, and live music venues. The street is a popular meeting place for tourists and locals alike, offering both daytime and evening entertainment, as well as opportunities for strolling and shopping.

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The picturesque Harborwalk is a lovely promenade, offering views of the water and the boats and ships. Numerous waterfront restaurants, snack bars, and pubs invite you to linger.

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Is also a museum and can be visited for an entrance fee

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der Kuhn
February 5, 2025, Duval Street

Duval Street Duval Street is a shopping street and a neighborhood in the center of Key West on the island of Key West in the Florida Keys, which stretches from the north to the south coast of the island. The district includes Duval Street on both sides of the street as well as the north end of Front Street with Wall Street, Mallory Square and the harbor of Key West. Duval Street is home to some of Key West's most famous restaurants and bars, including Sloppy Joe's, the Bull and Whistle, Rick's Cafe and Irish Kevin's bar. It is named after William Pope Duval, the first territorial governor of Florida. Source Wikipedia

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Frequently Asked Questions

How many urban hiking trails are available in the Florida Keys Wilderness?

The Florida Keys Wilderness offers over 50 urban hiking routes, primarily concentrated around Key West. These trails provide excellent opportunities to explore the unique urban landscapes and historical sites of the Keys.

What is the typical terrain and difficulty level for urban hikes in the Florida Keys Wilderness?

Urban hikes in the Florida Keys Wilderness are generally flat and easy, making them suitable for most skill levels. The terrain often includes paved paths, boardwalks, and compacted natural surfaces, allowing you to focus on the unique flora, fauna, and historical architecture without significant elevation changes.

Are there any family-friendly urban hiking routes in the Florida Keys Wilderness?

Yes, many urban routes in the Florida Keys are family-friendly due to their flat and easy nature. For example, the Southernmost Point – Tennessee Williams Museum loop from Key West is an easy 2.2 km walk that takes you past iconic Key West sights, perfect for families.

Can I bring my dog on urban hiking trails in the Florida Keys Wilderness?

Many urban areas and parks in the Florida Keys are dog-friendly, but specific regulations can vary by location. It's always best to check local signage or park websites for the most current rules regarding pets on trails. Generally, dogs on leashes are welcome in many public outdoor spaces.

Where can I find parking for urban hikes in the Florida Keys Wilderness?

Parking availability for urban hikes in the Florida Keys, especially in popular areas like Key West, can vary. Street parking, paid lots, and designated parking areas near trailheads or attractions are common. For routes starting in Key West, such as the Fort Zachary Taylor State Park – Southernmost Point Buoy loop, you may find parking within or near the state park, or in public garages downtown.

Is public transport available to access urban hiking trails in the Florida Keys?

In Key West, public transport options like the Duval Loop bus or local bus services can help you reach various points of interest and trailheads. For trails further afield in the Keys, accessing them typically requires a car, though some areas along the Florida Keys Overseas Heritage Trail may be accessible by local shuttles or taxis.

What is the best time of year for urban hiking in the Florida Keys Wilderness?

The best time for urban hiking in the Florida Keys Wilderness is typically during the cooler, drier months from November to May. Temperatures are more comfortable, and humidity is lower, making for a more pleasant experience. Summer months can be very hot and humid, with a higher chance of rain.

What kind of wildlife can I expect to see on urban hikes in the Florida Keys?

Even on urban hikes, you can encounter diverse wildlife. Keep an eye out for various bird species, iguanas, and unique insects. In less developed urban fringes, you might spot the endangered Key deer, especially on Big Pine Key, or even alligators in freshwater areas like the Blue Hole. The region's tropical hardwood hammocks and mangrove forests are rich in biodiversity.

Are there any notable landmarks or attractions along urban hiking trails in the Florida Keys?

Absolutely. Urban hikes in the Florida Keys, particularly in Key West, are rich with historical and cultural landmarks. You can explore sites like Fort Zachary Taylor Historic State Park, the iconic Southernmost Point Buoy, the Tennessee Williams Museum, and the Key West Lighthouse. The Tennessee Williams Museum – Key West Lighthouse loop is a great way to see several of these.

Are there urban hiking trails that are circular routes in the Florida Keys Wilderness?

Yes, many urban hiking trails in the Florida Keys Wilderness are designed as convenient circular routes. For instance, the Southernmost Point Buoy loop from Key West is a popular easy circular route, allowing you to start and end at the same point after exploring the area.

What are some examples of easy urban hikes in Key West?

Key West offers several easy urban hikes perfect for a leisurely stroll. The Southernmost Point – Tennessee Williams Museum loop is a short, easy walk, and the Tropic Cinema – St. Pauls Episcopal Church loop provides another accessible option to explore the city's charm.

Do I need any permits for urban wilderness trails in the Florida Keys?

Generally, permits are not required for casual urban hiking on public trails in the Florida Keys. However, some state parks or protected areas, such as Fort Zachary Taylor Historic State Park, may have entrance fees. Always check the specific requirements for the park or area you plan to visit.

Are there cafes or places to eat near urban hiking trails in the Florida Keys?

Given the urban nature of these trails, especially in Key West, you'll find numerous cafes, restaurants, and eateries conveniently located near many routes. You can easily grab a coffee or a meal before or after your hike, particularly around popular areas like Duval Street or near the historic district.

What should I wear for urban hiking in the Florida Keys Wilderness?

For urban hiking in the Florida Keys, lightweight, breathable clothing is recommended due to the warm and humid climate. Comfortable walking shoes are essential for paved and natural surfaces. Don't forget sun protection, including a hat, sunglasses, and sunscreen, as shade can be limited in some areas.

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