Cities Near Key West: Exploring 6 Hidden Gems

key west cities nearby sign
Everyone loves Key West, but if you want to see more of Florida, visit the cities near Key West.

Last Updated May 6, 2026

Are you planning a trip to Key West, Florida? If you’re looking to explore beyond the island and discover the charm of nearby cities and towns, you’ve come to the right place! 

Day Trip to Cities Near Key West

In this blog post, we’ll take you on a virtual tour of cities near Key West, highlighting the best destinations that are just a short drive away. Whether you’re into picturesque coastal towns, vibrant urban centers, or serene nature escapes, we’ve got you covered. 

Get ready to immerse yourself in the beauty and diversity of the cities close to Key West, Florida. Let’s dive in!

Why Visit Cities Close to Key West Florida?

Key West, Florida, offers a unique and vibrant travel experience, but exploring its neighboring cities and towns can enhance your trip even further. 

From the charming streets of Big Pine Key to the historic sites of Marathon and the natural beauty of Islamorada, these nearby towns offer diverse attractions, stunning landscapes, and authentic local experiences. 

Discover why visiting the cities and towns near Key West is a must for travelers seeking a well-rounded Florida adventure.

near Key West Hawks Cay Resort
Some of the best family resorts in the Florida Keys are in Marathon Florida like Hawks Cay.

Old Town Marathon Florida

The Old Town Marathon is a popular destination for travelers seeking a unique experience near Key West, Florida. This charming town offers a rich history, vibrant culture, and a variety of attractions that make it an ideal stop for those exploring the cities and towns near Key West.

Here is a list of things to do in Marathon, just a little over an hour from Key West:

  • Explore Sombrero Beach: Beautiful sandy beach perfect for swimming and sunbathing.

  • Experience the Dolphin Research Center: Get up close and personal with dolphins through interactive programs and shows.

  • Take a boat tour to Pigeon Key: Explore this historic island with its restored buildings and fascinating history.

  • Go fishing in the Gulf of Mexico: Charter a boat and try your luck at catching various fish species.

  • Enjoy water sports at Marathon’s watersports hub: Try jet skiing, paddleboarding, or parasailing for an adrenaline rush.

  • Visit the Turtle Hospital: Learn about sea turtle conservation efforts and see rescued turtles up close.

  • Indulge in fresh seafood at local restaurants: Sample delicious seafood dishes at waterfront eateries. Try the Angler and Ale for some of the off-the-boat fresh seafood.

  • Visit the historic Seven Mile Bridge: Take a scenic drive or walk along this iconic bridge connecting Marathon to the Lower Keys.

  • Enjoy a sunset cruise: Relax and admire the breathtaking sunset views over the Florida Keys’ turquoise waters.

If you have to pick and choose from these things to do in Marathon, we recommend Crane Point and the Dolphin Research Center. Our family loves both of these attractions in the Florida Keys.

towns near key west - key deer in big pine key
These Key Deer are a protected species only found in the Florida Keys.

Charming Big Pine Key

Big Pine Key boasts stunning natural landscapes, including the famous National Key Deer Refuge, home to the endangered Key Deer species. 

Visitors can immerse themselves in the island’s lush vegetation, uncluttered beaches, and crystal-clear waters, perfect for snorkeling, diving, and fishing enthusiasts. The laid-back atmosphere and friendly locals add to the island’s charm, making it an ideal spot for relaxation and rejuvenation.

  1. Explore Bahia Honda State Park – Pristine beaches and nature trails.
  2. Visit the National Key Deer Refuge – Spot endangered Key deer in their natural habitat.
  3. Go snorkeling or diving at Looe Key Reef – Discover vibrant marine life.
  4. Enjoy water sports at Big Pine Kayak Adventures – Kayaking, paddleboarding, and more.
  5. Take a scenic drive along the Overseas Highway – Enjoy breathtaking views.
  6. Discover the history of the Florida Keys at the History of Diving Museum.
  7. Visit the Blue Hole – A unique freshwater sinkhole attracting wildlife.
  8. Indulge in fresh seafood at local restaurants like No Name Pub.
  9. Explore the art galleries and shops in the Big Pine Key Shopping District.

Finding and observing Key Deer is a must in Big Pine Key.  Our secret for seeing them is going behind the Winn-Dixie Shopping Center. They scrounge for food in this area. Our grandkids have enjoyed watching these deer that are the size of a large dog.

See the Map of the Florida Keys below for the location of Big Pine Key.

Picturesque Stock Island

Stock Island, often overshadowed by its famous neighbor Key West, boasts its own distinctive charm. With its unspoiled natural beauty, including pristine beaches, lush mangroves, and breathtaking sunsets, Stock Island offers a serene and picturesque escape for travelers seeking tranquility away from the bustling crowds. 

The island is also home to a vibrant local community, where visitors can immerse themselves in the authentic Florida Keys lifestyle.

  1. Explore the Stock Island Marina Village: A vibrant waterfront destination with restaurants, shops, and live music.
  2. Visit the Key West Tropical Forest & Botanical Garden: Discover the diverse flora and fauna of this unique ecosystem.
  3. Enjoy fresh seafood at local eateries: Indulge in delicious seafood dishes at popular restaurants like Hogfish Bar & Grill.
  4. Discover the Stock Island Art District: Explore galleries and studios showcasing the work of talented local artists.
  5. Take a kayak or paddleboard tour: Experience the beauty of Stock Island’s mangrove forests and crystal-clear waters.
  6. Visit the Key West Golf Club: Play a round of golf at this scenic golf course located near Stock Island.
  7. Explore nearby towns like Big Coppitt Key and Sugarloaf Key: Discover charming communities just a short drive away from Stock Island.
  8. Experience the Stock Island Fishing Village: Join a fishing charter or visit the fish market to immerse yourself in the local fishing culture.
  9. Attend events at the Stock Island Cultural Center: Enjoy live performances, art exhibits, and cultural events in this vibrant venue. 

Of the above recommendations, no trip to Key West for us is complete until we get a Hogfish Sandwich at the Hogfish Bar and Grill on Stock Island. They have the best fish sandwich in Key West!

As you can see from the Map of the Florida Keys below, Stock Island is literally just over the Cow Key Bridge from Key West to Stock Island.

sunset bar grill - cities near key west
The Sunset Bar and Grill view at the base of the 7 mile bridge is one of the best tiki bars in Florida. That is a small pool next to the tiki bar!

Escape the Crowds: Discovering Serenity in the Lesser-Known Cities Near Key West

Stock Island and the following towns near Key West Florida are within 10 to 30 minutes.

Tranquil Sugarloaf Key

Tranquil Sugarloaf Key, located near Key West, Florida, offers a serene and picturesque destination for travelers seeking a peaceful getaway. Surrounded by stunning natural beauty, this hidden gem provides a perfect escape from the bustling city life. With its proximity to Key West and other charming towns in the region, visitors can easily explore the vibrant culture and attractions of the area.

Quaint Cudjoe Key – Closest City to Key West

Quaint Cudjoe Key is a charming destination located near Key West, Florida. This picturesque island offers a serene and laid-back atmosphere, making it an ideal getaway for travelers seeking a peaceful retreat. With its proximity to Key West and other nearby towns, Cudjoe Key provides easy access to a variety of attractions and activities in the region.

As the closest city to Key West, Cudjoe Key offers a unique regional experience that showcases the natural beauty and tranquility of the Florida Keys. Travelers can explore the stunning beaches, go fishing or boating in the crystal-clear waters, and immerse themselves in the vibrant marine life that thrives in this area. The island’s proximity to Key West allows visitors to easily access the lively nightlife, cultural events, and historical sites that the city has to offer.

Additionally, Cudjoe Key serves as a gateway to other towns near Key West, providing travelers with the opportunity to explore the diverse charm of the surrounding areas. From the historic streets of Key West to the quaint towns like Big Pine Key and Marathon, visitors can discover a range of attractions, including unique shops, local restaurants, and fascinating museums.

Cudjoe Key is a hidden gem for travelers seeking a peaceful and authentic experience in the Florida Keys. Its regional relevance lies in its proximity to Key West, as well as its convenient access to other towns in the area. Whether you’re looking for relaxation, outdoor adventures, or cultural exploration, Cudjoe Key and its surrounding cities offer a delightful escape for all types of travelers.

cities near key west - bahia honda state park sign
Just about 40 mins east of Key West, this is a great place to take your family.

Idyllic Summerland Key

Summerland Key, located in Florida, is an idyllic destination for travelers seeking a serene and picturesque getaway. 

Situated near Key West, this charming island offers a unique blend of natural beauty, recreational activities, and proximity to nearby cities and towns. Whether you’re looking to explore the vibrant city life or unwind in a tranquil setting, Summerland Key is the perfect destination for your summer vacation.

What To Do in Towns Near Key West Florida

  1. Explore the beautiful beaches: Summerland Key offers stunning beaches where you can relax and soak up the sun.
  2. Discover charming towns near Key West: Check out towns like Marathon and Big Pine Key, which offer unique attractions and local charm which are just minutes from Summerland Key.
  3. Enjoy water activities: Engage in snorkeling, diving, or fishing in the crystal-clear waters surrounding Summerland Key.
  4. Explore the Florida Keys National Marine Sanctuary: Discover the diverse marine life and coral reefs through snorkeling or boat tours.
  5. Visit Bahia Honda State Park: Experience the natural beauty of this state park, known for its pristine beaches and nature trails.
  6. Take a boat tour to Dry Tortugas National Park: Explore this remote park, home to Fort Jefferson and breathtaking snorkeling spots.
  7. Indulge in fresh seafood: Savor the delicious local seafood at the various restaurants and seafood shacks in the area.
  8. Enjoy outdoor activities: Engage in kayaking, paddleboarding, or biking to fully experience the scenic beauty of Summerland Key and its surroundings.

Summerland Key also has one of the most unique fly-in communities with its own airstrip just outside the resident’s front door.

Visiting the Cities Near Key West

In conclusion, exploring the cities close to Key West is an adventure worth embarking on. From the charming streets of Big Pine Key to the vibrant culture of Marathon, each destination offers its own unique experiences that are just a short drive away.

If you want to extend your vacation to the Florida Keys, there are many more islands to visit.

No matter if you’re seeking untouched beaches, thrilling water sports, or delicious seafood, these nearby Key West cities have it all. So pack your bags, hit the road, and discover the hidden gems waiting to be explored. Don’t forget to sign up for Florida Travel Blog for more tips and recommendations. Happy travels!

Frequently Asked Questions About Cities Near Key West Florida

What major city is near Key West?

Key West is pretty far from any major city — that’s part of its charm! The closest major city is Miami, but even that is about 160 miles away. If you’re driving, it takes around 3.5 to 4 hours because the Overseas Highway (US-1) is beautiful but slow, with lots of bridges and a 45 mph speed limit most of the way. Other major cities nearby-ish (but still not super close) are: Fort Lauderdale – about 180 miles away Naples (on the Gulf Coast) – about 200 miles (you’d drive north to Miami first, then cut across via Alligator Alley) So basically, Key West is out there all by itself, surrounded by water, coral reefs, and laid-back island vibes. If you’re heading there, the journey is half the fun! Want me to give you some cool stops to make if you’re driving from Miami to Key West?

Is Key Largo or Key West better?

Choosing between Key Largo and Key West really comes down to the type of experience you want. Key Largo is all about laid-back island life, outdoor adventures, and natural beauty. It’s known as the “Diving Capital of the World,” with easy access to coral reefs, snorkeling, kayaking, and fishing. It has a quieter, more local vibe with great seafood spots and small, cozy hotels. If you’re looking for peace, nature, and water activities without the big crowds, Key Largo is a perfect fit. On the other hand, Key West is the lively, colorful heart of the Florida Keys. It’s packed with historic charm, energetic nightlife, art galleries, festivals, and amazing sunsets. You’ll find iconic spots like Duval Street, the Hemingway House, and Mallory Square, where every evening feels like a party. Key West is better if you want a mix of culture, nightlife, sightseeing, and a little quirky island flair. Both places are beautiful, but they offer totally different vibes depending on what kind of getaway you’re dreaming about.

What cities are part of the Florida Keys?

The Florida Keys aren’t packed with a ton of big cities — it’s more like a chain of small towns, villages, and little communities strung along the Overseas Highway. But a few places are officially recognized as cities or incorporated areas. Here is a list of cities in the Florida Keys: Key West Marathon Layton Key Colony Beach Islamorada Remember, places like Key Largo, Big Pine Key and other well-known islands are significant communities, but are not official cities.

Is Key West closer to Miami or Cuba?

Key West is actually closer to Cuba than it is to Miami! Distance from Key West to Cuba: about 90 miles (straight across the water). Distance from Key West to Miami: about 160 miles (by land and bridges on the Overseas Highway). That’s part of why Key West has such a strong Cuban influence—especially in its food, culture, and history. You’ll find Cuban coffee shops, conch fritters (with Cuban roots), and a lot of local traditions that trace back to that connection

Map of the Florida Keys' Cities Near Key West

map of the Florida Keys cities near Key West
Google maps picture.

Sign up for our monthly updates and news about Florida travel. Join 21,000 other travelers!

larry edger _ author About the Author: I’m Larry Edger, a Florida resident who’s spent decades exploring the state—beaches, islands, springs, small towns, and road trips. I publish practical Florida travel guides with real-world planning tips and seasonal updates. Read more about Florida Travel Blog →

Can’t Find It? Search Florida Travel Blog

Florida Travel Blog is an Amazon Associate and other programs. Should you purchase something from a link, we earn a very small commission at no cost to you.

Latest Posts

Florida Travel Guides

Florida Travel Blog is an Amazon Associate. Should you purchase something from a link, we earn a very small commission at no cost to you.

Florida Itinerary Planner Link
what to bring to Florida

Kickstart Your Travel Plans With Florida Travel Blog

Travel smarter and with more adventure. We have been traveling the Sunshine State for 40 years! Join over 22 thousand other travelers who get our Florida travel updates monthly.

Sign Up for Florida Travel News