15 Best Old Towns in Florida in 2023 | Step Back in Time to Another Era

The Sunshine State’s rich history has produced some of the best old towns in Florida. Today, these once flourishing charming communities in historic times still offer a quaint and laid-back lifestyle that will make you feel like you’ve been transported back by a time machine.

The history of Florida was first recorded in the year 1513 when the Spanish explorer Juan Ponce de León discovered Florida while searching for the Fountain of Youth.

The more modern development of Florida started after it became an official territory of the United States in 1821 and then a state in 1845.

Since that point, many small towns and cities were established as part of the American Frontier and date back to this era. The majority of these old towns in Florida revolved around fishing and farming and still retains some of the historic architecture of that time period.

The best part about these old towns is that they are great for travelers as well as for living in. Their warm hospitality makes them easy to visit, while their simple way of life makes it easy to stay for the long-term.

Our team went through all the historical records and first-hand accounts to identify the best Florida old towns with a rich past that has maintained even today. 

Let’s find out what are the most beautiful and best old towns in Florida for your next visit or for you to move to.

15. Sanibel


Population: 7,401
Year Founded: 1832
Location: Check on Google Maps

Sanibel is one of the several historic old towns in Florida that is located directly on the beach. It is located right off the coast of Cape Coral and Fort Myers and offers a laid-back atmosphere that you cannot recreate on the mainland.

The island life is in full swing here, with beaches in every direction and small, locally owned stores lining its unhurried streets.

14. Punta Gorda

Population: 19,471
Year Founded: 1884
Location: Check on Google Maps

Punta Gorda is a small town just 30 minutes north of Fort Myers that sits right on the mouth of the Peace River in Charlotte Harbor.

It was well-planned when it was incorporated in the 1800s and still features a large set of public parks directly on the waterfront that is connected by a 2.5 mile long promenade.

Many of the historic streets downtown are still lined with bricks, which adds to the rich, preserved history of the city.

13. Port St. Joe

Population: 3,357
Year Founded: 1835
Location: Check on Google Maps

Port St. Joe is a small town on Saint Joseph Bay right on the Gulf in Florida’s Panhandle. It was once a bustling fishing port, but was devastated by several hurricanes.

Since then, this self-proclaimed “small town with a big heart” has reinvented itself while retaining its roots.

Today, Historic Downtown Port St. Joe is filled with numerous boutiques and restaurants that serve up the freshest and tastiest seafood dishes.

12. Brooksville

Population: 8,890
Year Founded: 1845
Location: Check on Google Maps

The streets of Brooksville are lined with historic, stately homes, century-old trees, and bricked-lined roads, making it one of the most quaint old towns in Florida.

Downtown Brooksville features a beautiful block of streets that bring back a feeling of nostalgia.

It is also just 1 hour from Tampa and 1.5 hours from Orlando, making it the perfect place to get away during your vacation or just for a long weekend. 

11. Apalachicola

Population: 2,341
Year Founded: 1820
Location: Check on Google Maps

Apalachicola’s real history dates back to the 1500s when it was still under Spanish rule. Its strategic location at the mouth of the Apalachicola River and Bay on the Gulf of Mexico made it a great place to settle.

Before the Civil War, Apalachicola was actually the 3rd busiest port on the Gulf.

Today, it still retains its charm as a well-preserved, historic old town of Florida.

10. Milton

Population: 10,197
Year Founded: 1844
Location: Check on Google Maps

Milton is one of the oldest towns in Florida and was one of the key industrial cities of Florida prior to the Civil War. Today, it still retains its small town charm while also offering the amenities of modern life.

There is a Historic District in Downtown Milton that has preserved the life and architecture that was seen in the 1800s.

9. Dunnellon 

Population: 1,928
Year Founded: 1887
Location: Check on Google Maps

Dunnellon is one of the smallest places on this list of the best old towns in Florida. It was once a famous area for mining and was actually quite a booming town.
These days, life is a bit more simple here, with local residents enjoying the popular Rainbow River for tubing and biking on the Withlacoochee State Trail.

There is also a historic downtown with small cafes, antiques shops, and unique restaurants.

8. Fernandina Beach

Population: 13,052
Year Founded: 1811
Location: Check on Google Maps

Fernandina Beach is one of the earliest built and also most beautiful old towns in Florida. This picturesque community features a 52-block historic downtown that is filled with lively bars and restaurants alongside stunning Victorian era homes.

Fernandina Beach truly encapsulates the idea of easy living and is popular with tourists and locals alike who are looking for a quaint place to just unwind.

7. Tarpon Springs

Population: 25,577
Year Founded: 1887
Location: Check on Google Maps

When it was settled in 1887, Tarpon Springs was actually the first incorporated city in what is now Pinellas County. It is located just 45 minutes from Tampa and is unique for having a rich Greek-influenced history. In fact, Tarpon Springs still has the highest percentage of Greek Americans in the whole US even today.

There are two historic districts in the city, Tarpon Springs Greektown Historic District and Tarpon Springs Historic District.

6. Anna Maria

Population: 968
Year Founded: 1892
Location: Check on Google Maps

The secluded town of Anna Maria is located on Anna Maria Island, which stretches 7 miles along the Gulf off the shores of Sarasota.

It is one of the smallest old towns in Florida on our list, with just under 1,000 permanent residents. But, it offers an old-time feel with a culture that is unhurried and always willing to take it easy.

5. Micanopy

Population: 648
Year Founded: 1821
Location: Check on Google Maps

Micanopy is believed to be the oldest community founded in the interior of Florida when it was established in 1821. It covers just 1 square mile and is located 20 minutes from Gainesville.

The town’s nickname is the “Little Town That Time Forgot” and features a historic downtown that was added to the National Register of Historic Places in 1983.

This idyllic town was even named one of the cutest small towns in America by the Huffington Post, making it easy to see why it is one of the best old towns in Florida.

4. Key West

Population: 26,444
Year Founded: 1829
Location: Check on Google Maps

Key West is the southernmost city in the US and has one of the most popular old towns in Florida. This tropical paradise just feels different compared to the rest of the state. It even feels like you are in a whole other country.

Today, Key West’s Old Town is the central hub of the city, where most tourists and locals spend their time. There are tons of laid-back bars and restaurants as well as sights to see like the Ernest Hemingway House and the Key West Museum of Art and History.

3. Mount Dora


Population: 16,341
Year Founded: 1880
Location: Check on Google Maps

No list of the best old towns in Florida can be complete without the charming town of Mount Dora.

This historic small town was founded in 1880 and offers a true sense of community with numerous annual festivals and events like the Mount Dora Arts Festival, Sailboat Regatta, and the famous Mount Dora Craft Fair.

The city also features a wide range of locally owned boutiques, gourmet restaurants, and quaint outdoor cafes, which adds to its old world atmosphere.

2. Cedar Key

Population: 687
Year Founded: 1839
Location: Check on Google Maps

Cedar Key is a quintessential waterfront fishing village and one of the best old towns in Florida today. Previously, Cedar Key was an important shipping port and railroad junction in the 1800s and was actually Florida’s 2nd largest city by 1880.

Since the decline of the railway, Cedar Key has embraced a slower lifestyle and is now one of the most charming and beautiful old towns in Florida.

1. St. Augustine


Population: 14,329
Year Founded: 1565
Location: Check on Google Maps

St. Augustine tops our list as the best old town in Florida for both visitors and for people looking to resettle. It is actually thought to be the oldest city in all of the US, having been founded in 1565 by the Spanish.

St. Augustine is also one of the most beautiful old towns in Florida. It features a dazzling, walkable historic district that is filled with the city’s best restaurants, bars, and shops.

Its stunning architecture is also a sight to see, with many buildings designed with a Spanish Colonial style that you cannot find anywhere else in America.

Summary – Best Old Towns in Florida

We hope this list of the best old towns in Florida has given you some insights of where you can escape back to another era in the Sunshine State. These towns have worked hard to preserve the positive aspects of their past while still offering a good way of life for its visitors and residents today.