The 10 Oldest Cities in Florida (And Which Are Best to Visit Today)

© Ingo70/

Written by Kristen Holder

Updated: June 16, 2023

Share on:


While humans have inhabited Florida for more than ten thousand years, the arrival of Europeans marked the beginning of modern recorded history. Currently, there are over 280 official cities in the state. What are the 10 oldest cities in Florida? Which are best to visit today?

Now read on as we provide lots of fascinating information below.

10. Gainesville Established in 1854: The Second Best Old City to Visit Today

What is Worth Visiting?Why is it Worth Visiting?
Devil’s Millhopper Geological State ParkThe large sinkhole that the park is based around offers three different habitats for exploring. There are also over 100 feet of exposed rock layers to see. Stairs wind down to an observation deck over a lake at the bottom of the hole.
Florida Museum of Natural History                      It’s free to visit! There are dinosaur bones and other fossils in their collection. The butterfly rainforest allows you to walk through a forested area full of live butterflies.
Haile HomesteadThe Haile family ran a plantation fueled by the labor of their enslaved people. In their house, they wrote heavily on the walls. The words are preserved, and guided history lessons address the history of slavery on the property. The homestead is only open on weekends.

While it isn’t certain if indigenous people had settlements in the Gainesville area, there is evidence of a Native American presence in the region dating back over 12,000 years. Europeans officially settled it in about 1854, which is a few decades after Florida was annexed into the United States.

Gainesville, Florida, USA

Gainesville, Florida, downtown skyline. Gainesville is also home to the University of Florida.

© Pavone

The oldest and biggest university in Florida is in Gainesville, called the University of Florida. The city is large for northern Florida, with a population hovering at a little under 150,000 people. The greater Gainesville metro area is home to over 300,000 Floridians.

9. Ocala Established in 1849

What is Worth Visiting?Why is it Worth Visiting?
Silver Springs State ParkThe water in the river of this park is fed by natural springs. This makes it crystal clear. Taking advantage of the water is best done by kayak and on glass boat tours.
Kanapaha Botanical GardensThere are 24 gardens planted along a pathway next to a lake. This walkway is paved, and it’s wheelchair accessible. It’s about a mile and a half long.

It’s believed that Ocala was established near a Timucua village of a similar name. The first European settlements may have existed in the sixteenth century but didn’t take root permanently. In 1849, Ocala officially became a city.

Ocala pinned on a map of Florida, USA

Ocala was established near a Timucua village of a similar name.

©Dmitrijs Kaminskis/

The United States Army built Fort King, which served as a focal point for the construction of Ocala around it. Equestrian activity is important in the city and generates over two billion dollars in revenue annually.

8. Marianna Established in 1828: The Most Underrated Old City in Florida

What is Worth Visiting?Why is it Worth Visiting?
Florida Caverns State ParkLarge caves with stalactites, stalagmites, and other rare features are available to explore. There is a small parking fee, and paid tours are available. Camping is also available.
Bellamy BridgeThis bridge is the center of a famous Floridian ghost story. A woman’s spirit continues to wander the area in search of her lover, who wasn’t buried nearby as planned. She’s been haunting the bridge for 160 years. Originally, a bridge from 1840 stood in the place of today’s bridge. It was replaced with what you see today in 1914.

Established in 1828, Marianna was primarily a hub for plantation owners in the region. Today, Marianna a small city with less than 10,000 residents. Its eastern border is the Chipola River. While the town isn’t a resort destination, the caverns and bridge offer entertainment beyond what is expected in the region.

chipola river

The Chipola River borders Marianna, Florida, on its east side.


Hurricane Micheal devastated the city in 2018. The hurricane damaged 80 percent of the businesses and homes in town. It also caused a power outage that lasted 3 weeks.

7. Tallahassee Established in 1824

What is Worth Visiting?Why is it Worth Visiting?
Lake Jackson Mounds Archaeological State ParkThere are two temple mounds from the indigenous Mississippian culture on view to the public.
Tallahassee Museum of History and Natural ScienceThis natural history museum is devoted to the history and wildlife of the Tallahassee area. Animals on display include bobcats, deer, red wolves, panthers, and bears.

Tallahassee has been the capital of the state of Florida since 1824. The city has a population of around 200,000 people, while the wider metropolitan area is home to almost 400,000. It is the largest city in the Florida Panhandle.

Blue Sky Behind White Clouds Over the State Capitol of Florida in Tallahassee

The State Capitol of Florida in Tallahassee, which has been the capital city since 1824.

©Blue Sky Behind White Clouds Over the State Capitol on Florida in Tallahassee/

There have been people inhabiting Tallahassee for thousands of years. The Spanish were occupying an Apalachee settlement in the area called Anhaica in 1538. This old town was about half a mile from the current capitol building.

6. Tampa Established in 1824

What is Worth Visiting?Why is it Worth Visiting?
Clearwater BeachClearwater Beach is just outside Tampa, boasting long, clean beaches and clear Gulf water. The Clearwater Marina Aquarium nearby is a great addition to a beach day.
Florida Museum of Photographic ArtsHistoric and contemporary photographs and artists are on display. This organization participates in community outreach so patronizing their establishment helps forward these programs.

The U.S. Army officially settled the Tampa area when they created Fort Brooke in 1824. Further development didn’t occur until 1845. In 1849, what was then called Tampa Town was officially incorporated. Tampa Bay hosts the seventh-largest commercial harbor in the United States.

Tampa, Florida - US State, Urban Skyline, University, South

A skyline view of downtown Tampa, Florida; its bay is the seventh-largest commercial harbor in the US.

© Pavone

After the Civil War and Yellow Fever chased off most residents, the locals voted to abolish the city’s government in 1869. It was successful, but the government was reestablished as growth occurred. The railroad and phosphate mining revived the area by 1900, and today it’s a large metropolis with satellite cities.

It’s considered one of the most vulnerable cities in the world because it will incur major damage if directly hit by a hurricane. A direct hit hasn’t occurred for 100 years, and the coastline has been extensively developed since the last disaster.

5. Jacksonville Established in 1822

What is Worth Visiting?Why is it Worth Visiting?
Jacksonville Zoo and GardensThere are a variety of animals on display, including locals, like the eastern diamondback rattlesnake, Florida bobcat, manatee, and gopher tortoise. There is an extensive planned garden showing plants from around the world.
Treaty OakThis huge tree is a 250-year-old Southern live oak growing in Downtown Jacksonville. It is in a park called Treaty Oak Park.

The Jacksonville area has played host to humans for over ten thousand years. In 1562, a French explorer charted the area. Within a few years, A settlement was established. Jacksonville’s location was largely influenced by its proximity to the mouth of the St. Johns River as it flows into the Atlantic.

Downtown Jacksonville, Florida

Downtown city skyline on St. Johns River in Jacksonville, Florida.

©ESB Professional/

The Spanish soon conquered the French and established a mission that was in use until the United States took control of Florida. It became a real town around 1822 as agriculture boomed in the region.

In 1901, a huge fire occurred that destroyed a chunk of the city. The smoke from the blaze was detectable 3 states away. This paved the way for modernization, and its current skyline began to develop.

4. Key West Established in 1822: The Third Best Old City to Visit in Florida

What is Worth Visiting?Why is it Worth Visiting?
Key West CemeteryOnly 30,000 people live in Key West today yet this cemetery is home to around 100,000 of its dead.
Southern Point MonumentThis is the most photographed tourist attraction in the keys. It states that it’s the southernmost point in the United States though this isn’t true.
Ernest Hemingway HouseThe family of Hemingway’s wife purchased this home which served as their permanent residence until they divorced. Today, polydactyl cats on the property are descended from his pets. There is also a penny in the concrete by the pool’s north side placed by Hemingway himself.

In 1822, a man claimed Key West for the United States. No one objected to this; the island has been a part of the United States since then. In the 1880s, Key West was the biggest and richest city in the state of Florida.

Aerial view of Key West in Florida

An aerial view of Key West, Florida, the southernmost point of the United States.

©Stuart Monk/

This key was also known as Cayo Hueso by the Colonial Spanish. That’s because the island was believed to be used as a graveyard by Calusa natives before European colonization. While the Keys were used throughout history, they weren’t permanently settled until the 1800s.

No other city is farther south than Key West in the United States. It connects to mainland Florida by a long highway called the Overseas Highway. This highway is also called US Route 1.  

3. Lake City Established in 1821

What is Worth Visiting?Why is it Worth Visiting?
Olustee Battlefield State ParkIn 1864, thousands of soldiers died in a Civil War battle at this location. This battle was Florida’s largest Civil War conflict.

Cannon used on the battlefield during the Civil War.


Founded in 1821, this city is located between Tallahassee and Jacksonville. When it was founded, it was called Alligator, and its location was chosen based on its proximity to an established Seminole settlement. Today, it’s a small city with a population hovering below 13,000 citizens.

2. Pensacola Established in 1698: The Best Old City to Visit in Florida Today

What is Worth Visiting?Why is it Worth Visiting?
Pensacola BeachThe waters are emerald in color and the 18 miles of beaches are made of white sand.
Plaza Ferdinand VIIIn this spot in 1821, Spain’s Ferdinand VII gave the USA control of Florida.

Pensacola is the most western panhandle city in the state of Florida. It boasts miles of coastline along the Gulf of Mexico, making it a popular destination for Georgians and Alabamans seeking leisure. The Blue Angels, which are a demonstration squadron for the US Navy, are based out of the Pensacola area.

Pensacola is not only one of the oldest cities in Florida, but it’s also the best vacation destination on this list. That’s because it boasts beautiful beaches with local amenities at affordable prices.

Discover the 10 Best National Parks in Florida Cover image

The beach in Pensacola, Florida, is part of the Gulf Islands National Seashore


There is legitimate evidence proving that Spanish Colonists established a settlement at Pensacola before the first permanent settlement in the United States was created. However, this initial settlement only lasted two years before falling into ruins. The Pensacola that remains today officially began in 1698 after being surveyed off and on for years.

1. St. Augustine Established in 1565: The Oldest City in Florida

What is Worth Visiting?Why is it Worth Visiting?
Old Slave MarketThis open-air market building was used to auction enslaved Africans to the highest bidder within the Plaza de la Constitucion.
Old Jail MuseumConstructed in 1891, this building held up to 72 inmates until 1953. A guided tour is available to see the building, with costumed actors as staff.

St. Augustine is on the Atlantic coast south of Jacksonville but still in its metropolitan area. It is the first place that Colonial Spain settled permanently and has remained inhabited since its inception in 1565. Some consider this city to be the oldest in the United States, while others support that San Juan in Puerto Rico is older.

St. Augustine in Florida

With a number of haunted locations, the city of St. Augustine is one of the most haunted places in Florida.

©Kevin Ruck/

St. Augustine was founded by a conquistador named Pedro Menéndez de Avilés. In 1964, it was the only place where Martin Luther King Jr. was arrested during his life. He was one of the main players in the violent protests centered in this city during the Civil Rights Movement.

Summary Of The 10 Oldest Cities In Florida

RankCityYear Established
4Key West1822
3Lake City1821
1St. Augustine1565

Share this post on:
About the Author

Kristen Holder is a writer at A-Z Animals primarily covering topics related to history, travel, pets, and obscure scientific issues. Kristen has been writing professionally for 3 years, and she holds a Bachelor's Degree from the University of California, Riverside, which she obtained in 2009. After living in California, Washington, and Arizona, she is now a permanent resident of Iowa. Kristen loves to dote on her 3 cats, and she spends her free time coming up with adventures that allow her to explore her new home.

Thank you for reading! Have some feedback for us? Contact the AZ Animals editorial team.