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Unearth the past: Explore the most charming historic towns in Florida

The state of Florida is a popular destination for beachgoers from across the country. But did you know that Florida is home to more than just a tropical paradise? That’s right: the Sunshine State also boasts a rich history. If you want to delve into the history of this unexpectedly storied state, you’ll need to add quite a few destinations to your travel wish list. So how will you choose which ones to visit?  

We’ve got you covered. In this guide, you’ll discover the most fascinating historic cities in Florida so you can start checking them off right away. To help you plan your trip, you’ll also find the closest SIXT branches to each town in Florida so you can hit the road in no time. Let’s get started!  

  1. St. Augustine: Florida’s Oldest City
  2. Fernandina Beach: One of the northernmost old towns in Florida
  3. Mount Dora: One of the most gorgeous old towns in central Florida
  4. Brooksville: A historic Florida town for nature lovers
  5. Dunnellon: One of the best historic towns in Florida for a blend of history and nature 
  6. Cedar Key: One of the best old towns in Florida for a quiet getaway
  7. Sanibel: One of the most relaxed historic towns in Florida
  8. Key West: One of the southernmost historic Florida towns 

1. St. Augustine: Florida’s Oldest City 

  • Region: Northeastern Florida 
  • Founded: 1565  
  • Where to pick your SIXT rental from: Jacksonville airport, 1 hour away  

Might as well start with the most historic city in Florida, right? Founded in 1565 by Spanish explorer Pedro Menendez de Aviles, St. Augustine existed long before the Pilgrims landed at Plymouth Rock. Forget about it being Florida’s oldest city – this is the oldest city in the entire US. This well-preserved, historic Florida town is like heaven for history and architecture buffs.

The remarkable Spanish-style buildings can be marveled at during a stroll through the coastal city’s historic old town. You’ll also want to visit the Castillo de San Marcos, a 17th-century fortress boasting unrivaled views of the Atlantic. The Mission Nombre de Dios is another point of interest along with its beautiful gardens. Museum lovers will enjoy a trip to the Colonial Spanish Quarter Museum, and those looking for something a little spooky will want to book a ghost tour. Aside from history, St. Augustine, as a coastal town, is also home to remarkable beaches and nature to be discovered, such as at Anastasia State Park. 

Most travelers visiting St. Augustine fly into Jacksonville International Airport. This makes the SIXT branch at the Jacksonville airport the perfect place to pick up your rental car. Enjoy a big selection of models, from midsize Nissan sedans to Chrysler minivans and get the one that is made for you.  

2. Fernandina Beach: One of the northernmost old towns in Florida 

A few hours north of St. Augustine, you’ll find the charming town of Fernandina Beach. This historic town in Florida is actually the northernmost on the Atlantic Coast, just south of the border with Georgia on Amelia Island. Known as one of the most picturesque cities in Florida because of its 19th-century Victorian architecture, this is one you won’t want to miss. While the city was officially established in 1811, the history of the area goes back to the 16th century. 

History buffs will want to hold onto their caps – Fernandina Beach is also known as the Isle of Eight Flags because it changed hands so many times. First, it was under the control of the French, then Spanish, English, Spanish again, then the Patriots, Spanish again, the Mexicans, the Confederates, and now, obviously, the Americans. If you need to walk through that progression slowly, visit the Amelia Island Museum of History. Other historic sites worth visiting include the Kingsley Plantation, where you can learn more about the history of slavery in this area, and Fort Clinch State Park, where you’ll encounter re-enactors who bring the past to life. A simple stroll through downtown checking out the quaint shops and restaurants will also ooze historical charm. For some beach time, head to Big and Little Talbot Island State Parks.  

The closest SIXT station to Fernandina Beach is again at Jacksonville International Airport. Make sure you have picked and booked your ideal car before you arrive, so you can find it waiting for you. You can add extras to your rental car, like a GPS, so you can always find your way.  

3. Mount Dora: One of the most gorgeous old towns in central Florida 

Just north of Orlando, you’ll find the adorable town of Mount Dora. Named after one Dora Ann Dawdy, a mid-19th-century homesteader known for her hospitality among federal surveyors, Mount Dora’s real growth as a town came in the 1920s. This hidden gem’s historic buildings still stand downtown today, allowing residents and visitors to enjoy their charm. A visit to The Donnelly House Museum is in order, where Mount Dora’s first mayor lived. You’ll also want to check out the Mount Dora History Museum and the Museum of Speed, where you can see an impressive collection of classic cars.  

Today, Mount Dora is known for its many antique shops and unique dining establishments. Collectors and window shoppers will enjoy ogling at all the fascinating finds. The Village Antique Mall and Renninger’s Flea Market & Antique Center are some of the most popular. Mount Dora also overlooks Lake Dora, and as a result, provides plenty of opportunities for outdoor recreation such as biking and kayaking. You may also want to check the town’s program for your travel dates; Mount Dora is known for its annual cultural festivals that draw thousands of visitors. 

Many people visiting this area will arrive in nearby Orlando by plane, so you can conveniently pick up your SIXT rental from the branch at Orlando International Airport. If you want to, you can select additional drivers, when you rent with SIXT. We can add up to 9 different drivers per booking. 

4. Brooksville: A historic Florida town for nature lovers 

Situated along Florida’s Nature Coast north of Tampa, Brooksville is a small rural town surrounded by sprawling countryside. Your introduction into the old-world downtown area will be a Confederate soldier statue just outside the courthouse. The downtown is lined with massive old oak trees and historic buildings housing unique boutiques and restaurants.  

Brooksville’s downtown is small, but the main historic draw will be the Chinsegut Hill Historic Site. This 114-acre pre-Civil War plantation is home to a well-preserved mansion that you can tour during weekends. In the 20th century, it became home to suffragists and other activists. You can also visit the 1885 Brooksville Train Depot and the Dade Battlefield Historic State Park. Withlacoochee State Forest is also located in Brooksville, which is why this is perfect for outdoor enthusiasts. It boasts some of the best hiking and biking trails in the entire country. The Weeki Wachee Springs are also nearby. Those looking for a less intense activity can visit the blueberry farms. 

Those visiting Brooksville will usually fly into Tampa International Airport. You can conveniently pick up a rental car from this airport and make your way to Brooksville. Browse through our selection of sedans, SUVs and family cars to pick the one that suits you.  

5. Dunnellon: One of the best historic towns in Florida for a blend of history and nature 

  • Region: Western Florida 
  • Founded: 1887 
  • Where to pick your SIXT rental from: Tampa International Airport, 1 hour and 30 minutes away 

A short drive north of Brooksville, we arrive in Dunnellon. This historic city in Florida was once nicknamed Boomtown after the discovery of phosphate in the area. This led to mines being built, railways being extended, and shops, hotels, and entertainment springing up in the downtown area. Those wanting to experience a blast from the past can tour the historic district, which is home to many antique shops and boutiques. You’ll also find plenty of local restaurants in the area serving a variety of cuisines.  

Today, Dunnellon is more famous for its natural attractions than it is for its mines. The historic town in Florida is home to Rainbow Springs State Park and the Rainbow River. This provides plenty of opportunity for kayaking, swimming, paddle boarding, and tubing. Those who would rather hike can visit the Halpata Tastanaki Preserve.  

As Dunnellon is located a short drive north of Brooksville, the closest SIXT station is at Tampa International Airport. A standard Toyota sedan might be the best option here. 

6. Cedar Key: One of the best old towns in Florida for a quiet getaway 

The second oldest town in Florida, Cedar Key is located on the Gulf Coast. After the Seminole War ended, the island became an important port for transporting goods to and from the mainland, but it still managed to avoid too much commercial development. This is where its charm lies: it’s got a quiet, small-town vibe that’s hard to come by these days.  

Cedar Key’s downtown area is home to many local shops, museums, eateries, and lodges that you can explore. Once a small fishing village, Cedar Key keeps up its reputation; it’s a great place to eat seafood, especially clams. If you want to partake in the fishing yourself, head down to the marina and the large fishing pier. If you feel like exploring, visit the Cedar Key National Wildlife Refuge. The keys that make up this refuge have incredible beaches to visit. You can even kayak around them if you’re feeling adventurous. One of the islands, Atsena Otie, is home to a real ghost town with ruins and an old cemetery. 

Cedar Key is about a 2-hour drive north of Tampa, so you can easily pick up your rental at the SIXT branch at Tampa International Airport. Select a Nissan compact sedan, to arrive comfortable and have no problem navigating Cedar Key once you get there. 

7. Sanibel: One of the most relaxed historic towns in Florida 

Located on Sanibel Island, the town of Sanibel was settled by the Florida Peninsular Land Company a little more than a decade before Florida joined the Union. Shortly thereafter, a lighthouse reservation was constructed and it’s still operational and maintained by the Coast Guard. You can tour the Sanibel Lighthouse today and visit the legendary boardwalk nearby. While Sanibel became an agricultural hub, much of it was destroyed in hurricanes throughout the 1900s, so it never became quite as industrious as some of the other old towns in Florida on this list. As a result, it’s said that Sanibel gives visitors a taste of the easygoing pace of life that was present in “Old Florida”. 

Today, Sanibel is famous for its pristine beaches and its relaxing vibe. It’s also a great shelling location, so natural history lovers will be in heaven here. You can even visit the Bailey-Matthews National Shell Museum. The J.N. “Ding” Darling National Wildlife Refuge is another major attraction in the area. 

Most visitors to this area will fly into nearby Fort Myers via Southwest Florida International Airport SIXT has a branch at this airport. You can book your rental before you arrive, using the SIXT app. 

8. Key West: One of the southernmost historic Florida towns 

  • Region: South Florida 
  • Founded: 1822 
  • Where to pick your SIXT rental from: Miami International Airport, 3 hours and 20 minutes away 

Key West, off the coast of the southern tip of the mainland, was claimed by the United States in 1822. But even before that, the Florida Keys had been visited by pirates and treasure hunters. The pirate era of Key West, however, was put to an end by the US Navy in 1822. You can still see the 200-year-old buildings as you stroll through the quaint downtown area visiting the local shops, cafes, restaurants, and more. 

The historic area is walkable and bikeable, and the weather is beautiful for exploring all year round. There are plenty of historic sites to see while you’re here, too. Check out the Hemingway Home and Museum to explore the 1930s residence of the famed writer. Head to Fort Zachary Taylor Historic State Park to discover a Civil War-era fort and cannons. You can also visit the Truman Little White House and the Key West Lighthouse. Aside from the historical attractions, Key West is famous for its beaches that are amazing for swimming no matter what time of year you decide to visit. If you’d rather enjoy the water from afar, you can go fishing. There’s also plenty of hiking in the surrounding area.  

Those visiting Key West will typically arrive via Miami International Airport. SIXT has a branch at this airport where you can pick up a car and continue your drive a few hours down to Key West. Just to be safe, review an extra protection plan. 

Now that you’ve discovered some of the most exciting historic towns in Florida, you can hit the road! Of course, you’ll want to see more than one, so why not make it a road trip? Rent a car from SIXT to get you from one of these old towns in Florida to the next and everywhere in between. Happy travels!