5 of Florida’s Oldest Cities to Honor the Past and Celebrate the Present

St. Augustine, Florida at the Castillo de San Marcos National Monument at dusk. Image via Sean Pavone / Shutterstock

By Cynthia De Saint

November 3, 2022

These vibrant cities across the Sunshine State preserve the fascinating history that makes each one as unique as it is old.

Europe’s greatest cities usually come to mind when we think of places rich with remnants of centuries past. But, did you know that our very own Sunshine State is home to some of the most historic places in the country? From the first European settlement in America to the site of the legendary Fountain of Youth, here are five cities in Florida where you can time-travel to the past while enjoying the best the present has to offer.

St. Augustine

Soon after Spanish explorer Juan Ponce de León first landed in the area in 1513, Spain began establishing settlements around Florida. In 1565, St. Augustine was founded, and the Spanish continued to develop several other cities until Florida was formally ceded to the United States in 1821. 

Today, the Sunshine State’s oldest city is remarkably well-preserved, with unique attractions like stately castles, Gilded-Age hotels, and a spiraling lighthouse, alongside scenic nature trails and tranquil beaches. 

At the Colonial Quarter, visitors can experience three centuries of the city’s vibrant past through interactive activities that make history come alive. Then, there’s the chance to “rejuvenate” with a visit to Ponce De Leon’s famed Fountain of Youth archaeological site and drink from the famous springs. Also visit the oldest schoolhouse in the country, tour the historic and imposing Castillo de San Marco with its views of the Atlantic Ocean, or just stroll along the brick-lined streets and delight in the city’s European flavor. 

Learn more about St. Augustine’s history and attractions HERE.


5 of Florida's Oldest Cities to Honor the Past and Celebrate the Present
Image via Cheryl Casey / Shutterstock

Founded in 1698 and settled by the Spanish in 1559, Pensacola was settled six years before St. Augustine and 48 years before Jamestown, Virginia.  That is why the welcome sign in downtown Pensacola cites the city as “America’s 1st Settlement.”

However, it didn’t last very long, as after two years the Spanish decided that area was too dangerous to settle. They did return in 1698 to establish an outpost that eventually grew into the modern city.

And what a city it is for history buffs! Historic Pensacola, for example, encompasses 28 properties within the original Spanish and British forts in downtown Pensacola, where visitors can participate in guided and self-guided tours of historic homes and interact with period-dressed living history interpreters. 

Then, there’s Fort Barrancas, the famed Pensacola Lighthouse and Maritime Museum, where kids can play through the city’s 450-year history with interactive, imaginative, and educational play for all ages.

Learn more about Pensacola’s history and attractions HERE.

Key West

5 of Florida's Oldest Cities to Honor the Past and Celebrate the Present
Image via majicphotos / Shutterstock

Only 90 miles from Cuba, the southernmost post in the US was first visited by the Spanish after Juan Ponce de León came to the island in 1521. Fast forward to 1822, when Lt. Commander Matthew C. Perry claimed Key West for the U.S. and it became American property.

Today, Key West is one of the country’s hottest, hippest spots starting with Duval Street, one of the most energetic strips of shops, bars, and cafes anywhere. Fans of famed American writer Ernest Hemingway can toast at Sloppy Joe’s bar, a favorite hangout of the novelist. And at the Ernest Hemingway Home and Museum, visitors are sure to encounter his celebrated six-toed cats.

Walking tours of Key West are a great way to see the island’s fascinating homes, courtyards, and gardens. And be sure not to miss the island’s outdoor art, from offbeat large-scale sculptures to murals promoting ocean conservation. You can also explore the town’s history at sites such as Fort East Martello and Fort Zachary Taylor Historic State Park, defensive fortresses that date back to the 19th century. Of course, beach lovers can find plenty to enjoy with diving, snorkeling, boating, and so much more. 

Finally, as the sun sets each day, locals and tourists head to Mallory Square to join in a toast surrounded by performers. 

Learn more about Key West’s history and attractions HERE


5 of Florida's Oldest Cities to Honor the Past and Celebrate the Present
Image via Sean Pavone / Shutterstock

This vibrant city has been the state’s capital since the city was officially established in 1824 by the state legislature. But before the first Spanish missionaries were sent to the area in the 17th century, Tallahassee was inhabited by the Apalachee tribe. 

Today, visitors will find a 10-block historic district around the capitol complex with a famed inn and bars and restaurants for every taste. Art lovers are sure to enjoy the Downtown Industrial Park, where artists have turned the old warehouses into the studios and cafes of Railroad Square, and the nearby Museum of Florida History will delight history buffs. 

Visiting with kids? The Tallahassee Museum of History and Natural Science combines a natural habitat zoo for native animals with a collection of historic structures, including a 19th-century farm, a one-room schoolhouse, and a plantation mansion. 

There’s also plenty for nature lovers. Alfred B. Maclay State Gardens Park, a masterpiece of floral architecture, enchants visitors with a secret garden, a reflection pool, and hundreds of camellias and azaleas. 

Learn more about Tallahassee’s history and attractions HERE.


A small city in Jackson County, beautiful Marianna nestles along I-10 just under the Florida-Alabama border and a brief drive west of Tallahassee. Known as the “The City of Southern Charm,” it was founded in 1827 by Scottish entrepreneur Robert Beveridge and believed to be named either after his wife, Anna Maria, or his daughters, Mary and Anna.

Visitors can stroll through the city’s quaint streets with its many historic buildings and large canopy oak trees. The triangulated courthouse park with its gazebo, and the nearby obelisk marking the Civil War Battle of Marianna are just two of the city’s many marvels. 

But without a doubt, ecotourism is the star of this beautiful spot blessed with miles of spring-fed rivers, lakes, ponds, and paddling trails. Kayak, canoe, and paddle board enthusiasts are drawn to the area to explore the Chipola River. 

A not-to-be-missed spot when you visit Marianna is the Florida Caverns State Park, which boasts the state’s only dry caverns along a quarter-mile trail. And for a real ghoul time, the Bellamy Bridge Heritage Trail leads to the oldest bridge of its type in Florida, which is the locale for one of the city’s best-known ghosts. The restless spirit of a young woman named Elizabeth Jane Bellamy is said to roam the swamps around the bridge on dark and foggy nights. 

Learn more about Marianna’s history and attractions HERE.




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