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15 Best Old Towns in Florida (History, Insight & More!)

15 Best Old Towns in Florida (History, Insight & More!)

Florida has a rich history and plenty of old towns to explore. The state is full of unique communities, where you can find culture, natural beauty, and the charm only an older town can offer.

We’ve scoured the Sunshine State to bring you this list of the 15 Best Old Towns in Florida that are perfect for a day trip or weekend getaway!

15 Best Old Towns in Florida

The nicest aspect about these ancient settlements is that they are ideal for both tourists and long-term residents. Their open-air atmosphere makes them easy to reach, while their simple way of life makes it simple to reside in for the long run.

Let’s look at the most lovely and historic towns in Florida for a trip or to relocate to.

1. Milton

Milton is located in Florida’s so-called Emerald Coast, which runs along the state’s beautiful panhandle. The town itself is very small, but still has plenty of charm. The area was first settled in the early 1800s and became an official city 10 years later.

Since then it has served as a popular spot for hunters and fishermen, but today its economy is largely based around the tourism industry. The city boasts some lovely historic architecture including 19th century Victorian-style homes, while it also offers plenty of entertainment options for visitors.

2. Cedar Key

Cedar Key is a small town situated on an island along the Gulf Coast. With a population of just less than 1,500 people, it’s actually one of the largest cities in Levy County and home to Cedar Keys National Wildlife Refuge.

The city has a strong maritime tradition and fishing is still important to the local economy. The town’s architecture dates back to the 1800s, when it was founded as a shipbuilding hub for locals.

Today boat captains can take out visitors on eco-tours in search of manatees, sea turtles and other wildlife in the area.

15 Best Old Towns in Florida (History, Insight & More!)

3. Port St. Joe

Port St. Joe was founded in the 1840s by an ex-Confederate soldier turned real estate developer named A.B. Bailey, who also served as the city’s first mayor. The city itself has two distinct areas: Port St. Joe and Mexico Beach.

The former is home to most of the old Florida homes, churches and government buildings. The latter is located on the widest portion of Saint Joseph Bay and features a long, pristine stretch of beaches.

A few years ago the town was hit by Hurricane Michael, which destroyed much of its buildings and businesses. However today it has made a remarkable comeback with plenty of hotels and restaurants catering to tourists and locals alike.

4. Punta Gorda

Punta Gorda calls itself Florida’s Oldest City. The title is somewhat questionable, as it was only officially incorporated in 1887. That said, the city has a rich history and plenty of historic homes dating from the early 19th century, so it’s definitely one of the most interesting ancient cities in Florida.

In fact Punta Gorda’s historic section has been recognized as a National Register Historic District. The city boasts a number of fascinating attractions, including waterfront parks and gardens, while it is located on Charlotte Harbor, which is one of the most protected bays in the world.

5. Key West

Key West is one of the most famous and popular destinations in Florida. Most tourists flock to this city which has a reputation as a party town – but there’s so much more to it!

A lot of Key West’s historic architecture dates back to its early days as an important port, while today visitors can marvel at Spanish Colonial architecture and enjoy views over Fort Zachary Taylor.

For those who want to experience the Florida Keys without the party scene, Key West is also home to Old Town, which features a charming New England-style commercial area.

6. St. Augustine

St. Augustine is Florida’s oldest city and one of the oldest in America, founded by Spanish explorer Juan Ponce de Leon in 1565.

It was a major port during all three Spanish centuries and served as an important military outpost. Today it’s known for its historic buildings and related attractions including Castillo de San Marcos National Monument and Fort Matanzas National Monument.

St. Augustine also has plenty of museums, most of which are focused on local history or marine life in the area, while it’s one of Florida’s best places to eat Spanish food and other Caribbean specialties.

7. Tarpon Springs

Tarpon Springs is located near the southern tip of Pinellas County, about halfway between Tampa and St. Petersburg.

It’s best known for its sponge diving heritage which dates back to the 19th century when Greek immigrants began harvesting sponges from local reefs. Today you can still go scuba diving near Tarpon Springs in the Sponge Docks area and bring back a real, live sponge!

In addition to being one of Florida’s most popular dive sites, Tarpon Springs has some great attractions for visitors including art galleries, traditional Greek restaurants and shopping.

8. Fernandina Beach Florida

Fernandina Beach is a city located on Amelia Island, just a short drive from Jacksonville.

The town’s history dates back to the late 18th century – during the time of Spanish Florida – and today it has a number of interesting attractions including Fort Clinch State Park, which was built by Union troops during the Civil War.

9. Dunnellon

Dunnellon is located in Marion County, close to the Rainbow River.

The city is best known for its historic downtown area, which was almost entirely built between 1890 and 1920. Today you can explore the town’s brick-paved streets and admire some of its charming historic buildings, while dining at one of Dunnellon’s restaurants will give you the chance to sample some Florida’s best cuisine.

10. Apalachicola

Apalachicola is a coastal city in Franklin County, which is located at the northern end of the Florida Panhandle.

The town was established in 1831 and its historic district has been recognized as a National Register Historic District since 1972.

Today Apalachicola is a great place to visit – both for its history and for its local seafood scene, which includes some of Florida’s best restaurants.

11. Brooksville

Brooksville is located in Hernando County, just north of Tampa.

This city was established during the 19th century and early settlers made their living by working in sawmills or harvesting timber from nearby forests. Today visitors can enjoy local museums and a number of great restaurants including a fried chicken joint in downtown Brooksville that’s been around since 1901!

12. Micanopy

Micanopy is a town located in Alachua County. As the name suggests, Micanopy was founded by people from Seminole Native American groups and today it’s one of Florida’s oldest towns, established during 1849.

Today the city has some great old buildings, in addition to being well known for its artist community and annual Micanopy Fall Festival.

13. Sanibel

Sanibel is located on Sanibel Island, which is located just off the Gulf of Mexico and to the west of Fort Myers.

The town’s population was 818 at the 2010 census and it has a permanent year-round population that hovers around 3,000 people during the winter months.

14. Anna Maria

Anna Maria Island is located in the heart of Florida’s west coast region, just off Bradenton. Getting there is easy, since you can drive on the Anna Maria Island Bridge from Bradenton or catch the ferry from nearby Longboat Key.

The town has a permanent population that hovers around 3,700 people and during the winter months its population increases dramatically when snowbirds flock to the island to escape harsh winters in other parts of the country!

15. Mount Dora

Mount Dora is a city located north of Orlando, was established during 1870 and today it’s a very popular tourist destination.

Mount Dora has numerous styles of architecture, including Victorian homes which range from small cottages to mansions that have been restored with modern amenities for today’s visitors.

At Mount Dora you’ll also find interesting museums, including the Modernism Museum of Education and Natural Science.

History Overview of Florida

Some of the state’s most beautiful old towns can be found in Florida. Today, these formerly flourishing charming villages provide a lovely and laid-back atmosphere that will make you feel like you’ve traveled back in time.

Florida’s history was first documented in 1513, when the Spanish explorer Juan Ponce de León located it while looking for the Fountain of Youth.

Florida’s history dates back to the days of Spanish exploration, when it was used as a refuge before being settled. After becoming an official territory of the United States in 1821 and then a state in 1845, development became more modern.

Florida is the southernmost state in the United States, bordered on the Atlantic Ocean to the west and the Gulf of Mexico to the east. It has massive golden beaches. Miami is known for its Latin American cultural influences, a thriving arts scene, and South Beach’s late nightlife, particularly in South Beach. Walt Disney World is known for its theme parks.

Reasons to Find the Best Old Towns in Florida

Having any new destination on your Florida itinerary is a great idea for a variety of reasons. However, one thing that you may not realize until you start looking into these new destinations is how many old towns there are in Florida.

Old Towns of Florida

There are a number of beautiful old towns in Florida that have a lot to offer tourists.

  • One of the most popular towns is Augustine, which is located near St. Augustine Beach. This Florida town gets its name from the Spanish explorer who was responsible for naming this area.

*This town has gone through a lot of changes over the years, but it still holds on to many of its old world traditions and historical sites. Because of this, you can easily spend a few hours or even a few days in this town without ever getting bored.

  • Another great old town that you will find when visiting Florida is Fernandina Beach. This beach is one of the oldest in all of North America and has been well known for its fishing and boating industries throughout history. Today, visitors flock to the area to enjoy the great fishing, beautiful beaches and nice old Florida style.

*The population may have increased throughout time, but it still remains one of the best places in all of Florida for those who want to step back in time a little bit. The quaint shops located along Centre Street are just one example of this town’s dedication to its past traditions.

  • Another popular old town in Florida is Hastings. This little spot has gained a lot of attention throughout the years for its special events, historic architecture and quaint small town charm.

*Tourists who are looking to get away from it all while still having access to some great historical sites will find that this is one of the best old towns in Florida.

As you can see, there are a number of other great old towns in Florida. When you come to the Sunshine State, make sure that you spend time exploring one or two of these towns. You will not be disappointed with what they have to offer! 

Now, let’s talk about the reasons:

  1. They are historical, having landmarks and artifacts that can give clues to what life was like in the past.
  2. Many of them have old world charm because they have not changed much over time to accommodate tourism or modern industries.
  3. These towns often contain unique shops and restaurants so you can experience different types of cuisine than you would find in more touristy spots.
  4. In many of these towns you have the opportunity to meet residents who have been living there for generations. You can get a feel for what life is like from those who have some great historical memories as well as their own stories about how things used to be.
  5. The architecture of the buildings often reflects designs from another era, giving them a different look than you might find in other parts of the state. The buildings are often quaint and charming, which adds to the old world feel of these towns.

The people who live in these towns typically take pride in their communities and are happy to share what makes them so special with those visitors who come to this part of Florida on vacation. Many of these residents understand the history behind their towns and are more than willing to share it with you.

In many cases, weekly events keep these town’s traditions and allow visitors to learn about past times when people used to celebrate in this way. You can usually obtain some great deals on things like antiques, collectibles and other items that you might not be able to find just anywhere.

15 Best Old Towns in Florida (History, Insight & More!)


Therefore, if you’re looking for some of the best old towns in Florida, then check out these 15 amazing places that will transport you back to a simpler time.

We hope this list of the greatest old towns in Florida has provided you some ideas on where to go back in time. These communities have fought hard to keep the pleasurable aspects of their history while still providing a nice lifestyle for its visitors and residents today.