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! 

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 Key West’s Neighboring Cities and Towns?

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 destinations provide 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.

Old Town Marathon

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, Florida:

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

• Visit the Florida Keys Aquarium Encounters: Interact with marine life through snorkeling, feeding, and touch tanks.

• Discover the Curry Hammock State Park: Enjoy hiking trails, kayaking, and picnicking in this scenic coastal park.

• 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.

• Explore the Crane Point Museum and Nature Center: Discover the natural and cultural history of the Florida Keys.

• 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 of 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.

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 location.

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.

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

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 one of the cities near 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.

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.

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 near 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.

Whether you’re seeking untouched beaches, thrilling water sports, or delicious seafood, these nearby cities have it all. So pack your bags, hit the road, and discover the hidden gems waiting to be explored. Don’t forget to check out our related resources for more tips and recommendations. Happy travels!