The historic and popular Sloppy Joe's Bar on Duval Street in downtown Key West. Editorial credit: Fotoluminate LLC /

9 Oldest Founded Towns to Visit in Florida

Florida is a tourist hotspot, famed for its scenic views, rich culture, and beautiful weather. From sunbathing along the Atlantic Ocean to experiencing the vibrant nightlife in cities like Miami, the state has a myriad of amazing activities on offer. In addition to these attractions, the “Sunshine State” is also a hub of history and heritage, with some captivating stories to share. The best way to explore this is in Florida’s oldest-founded towns, which showcase rustic structures away from the bustling crowds. Moreover, with a wealth of interesting tales and tours, one can have an unforgettable vacation in these historic Florida towns.

St. Augustine

Waterfront view in St. Augustine, Florida
Waterfront view in St. Augustine, Florida

St. Augustine, founded in 1565, is the oldest continuously occupied European-established settlement in the continental United States. Initially inhabited by indigenous peoples, it was first settled by the Spanish. The town has witnessed many significant events, including pirate invasions, the Civil War, and the Civil Rights Movement. As such, it is a treasure trove of historic significance, offering a plethora of landmarks, museums, and activities. History enthusiasts can begin their journey at the Castillo de San Marcos National Monument. Constructed in the late 1600s, this fort is the oldest masonry fortification in America and an ideal place to delve into the town’s early history. Progress through time with a visit to landmarks like the Fort Mose Historic State Park, Old Jail, or the Gonzalez-Alvarez House. From recounting the story of Martin Luther King Jr.’s arrest during the Civil Rights Movement to showcasing Spanish architecture, these sites offer days' worth of exploration. Additionally, museums such as the Villa Zorayda Museum and St. Augustine Pirate & Treasure Museum provide intriguing insights into the past.

Beyond its rustic streets and ancient exhibits, St. Augustine, with a population of around 14,300, is vibrant and lively. As a popular tourist destination, you’ll find it easy to make new friends in town. Places like Vilano Beach offer a serene spot to relax and bask in the sun. Alternatively, visit the St. Augustine Distillery for free tastings, exceptional bourbon, and unique souvenirs. All in all, if you're interested in visiting the oldest town in both Florida and the continental United States, St. Augustine is an unparalleled choice.

Lake City

Marion Avenue in Lake City
Marion Avenue in Lake City, Florida

A bit more recent than St. Augustine, Lake City offers a blend of history and entertainment. The area, originally known as Alligator Village, a Seminole community, evolved into Lake City and became the seat of Columbia County in 1832. Now a suburban town with over 12,000 residents, Lake City provides visitors with a glimpse into its 200-year history. Notable sites include the Columbia County Courthouse (built in the 1960s), Hotel Blanche, and Columbia County Bank Building. The courthouse, in particular, is renowned for its Classical Revival architecture. For those seeking deeper insights, the Lake City Columbia County Historical Museum displays a rich collection of photos, artifacts, and memorabilia.

Lake City's prime location between Tallahassee and Jacksonville makes it easily accessible, whether by flight or road. After delving into history, visitors often enjoy the peaceful ambiance of Alligator Lake Park or the natural beauty of Falling Creek Falls. Lake City, with its fascinating history and picturesque scenery, is a delightful destination.

Key West

Tourists walking in front of the La Concha Hotel and Spa in Key West.
Tourists walking in front of the La Concha Hotel and Spa in Key West.

Key West is more than a historic town; it's one of Florida’s top tourist resorts, known for its watersports, nightlife, beaches, and historic sites, reminiscent of a Caribbean paradise. Its history is equally intriguing, with early visits in the 1700s and official U.S. acquisition by John W. Simonton in 1822. Key West flourished in the late 19th century, partly due to its lucrative shipwreck salvaging industry. Today, visitors can immerse themselves in this history at the Ernest Hemingway Home and Museum, Fort Zachary Taylor Historic State Park, and Harry S. Truman Little White House, each offering unique glimpses into Key West's past.

Key West’s present is a vibrant mix of coastal activities. Visitors can enjoy sunbathing on its beautiful beaches or exploring the Key West Butterfly and Nature Conservatory, home to hundreds of exotic butterflies. As evening falls, Duval Street comes alive, offering an endless array of bars, cafes, and shops. Key West masterfully blends its rich history with a lively, contemporary resort atmosphere, making it an ideal vacation spot.


Street view in Marianna, Florida
Street view in Marianna, Florida, via Stillgravity /

Head inland from Key West to Marianna, a tranquil retreat in Jackson County. Home to fewer than 7,000 residents, this town blends a peaceful atmosphere with a rich history, having been established in 1828. Marianna has weathered significant events, including a Civil War battle in 1864 and substantial damage from Hurricane Michael in 2018. Today, it stands as an appealing destination for family travelers. The Historic District, with nearly 200 buildings, offers a glimpse into Marianna's past, featuring structures like the Erwin House, Great Oaks, and Holden House, each telling its own story. For a hauntingly historical experience, visit the Bellamy Bridge Heritage Trail, known for its ghostly legends.

For outdoor enthusiasts, Florida Caverns State Park is a highlight, offering guided tours through its fascinating limestone caves. Alternatively, the Blue Springs Recreation Area provides a picturesque setting for swimming, kayaking, and paddle boating, all for an affordable entry fee of $4.


Shops in Quincy, Florida
Shops in Quincy, Florida, via Joanne Dale /

After Marianna, consider visiting Quincy, another town rich in history. Founded in 1828 and named after President John Quincy Adams, Quincy developed a robust agricultural economy, particularly in tobacco. The town's historic district showcases Antebellum architecture across 150 buildings, with notable sites like the Smallwood-White House and Stockton-Curry House. The Gadsden Arts Center & Museum is also a must-visit for those interested in local artistic heritage.

Quincy's proximity to Tallahassee, just 30 minutes away, adds to its appeal. Adventure-seekers can explore skydiving opportunities, while nature enthusiasts will find Lake Talquin State Forest, near Quincy, an excellent spot for boating, hiking, and camping amidst Florida's natural beauty.

Cedar Key

An American flag on a street in historic downtown Cedar Key, Florida
An American flag on a street in historic downtown Cedar Key, Florida

Inhabited for over 2,000 years, initially by indigenous peoples, Cedar Key is steeped in coastal history. The town's transformation began in the 1840s, evolving into a significant fishing town and port, especially following the arrival of the Florida Railroad in the 1860s. Despite challenges like the Civil War and environmental concerns, Cedar Key has emerged as a popular tourist destination. Visitors can enjoy the Cedar Keys National Wildlife Refuge and Lower Suwannee National Wildlife Refuge, offering opportunities for boating and hiking amidst stunning natural scenery. Keep an eye out for local wildlife, including Atlantic Horseshoe Crabs and Great Egrets. For seafood enthusiasts, restaurants like 83 West and Steamers Clam Bar & Grill serve delicious local catches.

The Cedar Key Historical Museum, located in the historic Lutterloh and Andrews Houses, provides a comprehensive look at the town's past, from prehistoric times to modern growth.

Fernandina Beach

Palace Saloon in the Famous Prescott Building in Fernandina Beach.
Palace Saloon in the Famous Prescott Building in Fernandina Beach. Image credit Dietmar Rauscher via Shutterstock

Amelia Island, home to Fernandina Beach, is a town rich in Southern charm and history. Known as the “Isle of 8 Flags,” it has seen various nations' flags raised since the 1500s, starting with French explorer Jean Ribault in 1562. The island's strategic location led to numerous battles and changes in ownership, culminating in Fernandina Beach's development as one of the last towns platted under Spanish rule in the Western Hemisphere.

Today, as the county seat of Nassau County, Fernandina Beach is a hub of waterfront attractions and history. A stroll through Centre Street reveals Victorian-era buildings and antique stores. Visitors can explore Fort Clinch State Park, the Amelia Island Museum of History, and the Amelia Island Lighthouse, each telling a part of the island's diverse history.

The town also offers ample entertainment, from the pristine beaches of Main Beach Park to the locally crafted spirits at Marlin & Barrel Distillery. With its blend of history and modern attractions, Fernandina Beach is a captivating destination.


The famous Pensacola Beach water tower in Pensacola Beach, Florida.
The famous Pensacola Beach water tower in Pensacola Beach, Florida.

First settled in 1559 by Don Tristan de Luna, Pensacola is one of Florida's oldest communities. Despite the initial settlement facing challenges, the city thrived under various rulers, earning its nickname “The City of Five Flags.” Its rich history is palpable in its streets, lined with Spanish forts, British memorabilia, and Civil War stories. Cultural destinations such as the 1834 Fort Pickens, Pensacola Lighthouse & Museum, and Historic Pensacola Village bring this history to life. These sites narrate tales from Spanish military strategies to the Civil War fort that never fell. Pensacola is also known for its significant military presence, including the Naval Air Station Pensacola.

As you explore the city, its beautiful beaches offer popular activities like sunbathing, swimming, and volleyball. Small stores and cozy cafes near the beachfront provide perfect spots to relax with the soothing backdrop of the ocean.


The city hall in Freeport, Florida
The city hall in Freeport, Florida

In Walton County, Freeport is a serene suburban community. Established in 1830 and initially named “Genoa,” it was later renamed Freeport, reportedly because the port didn’t charge fees. The town, once home to farmers and fishermen and supported by a robust timber industry, saw its growth taper off in the 1900s. Today, it balances tourism with the presence of Eglin Air Force Base.

While Freeport may not have as many historic landmarks as other towns, it's still rich in history. The Heritage Center of Freeport, Freeport Memorial Park, and the Old City Hall each have their own stories, from honoring war veterans to commemorating local business and military history. For those seeking different experiences, the town offers animal refuges, golf courses, and parks, ensuring there's something for everyone.

Each of these towns in Florida, from Pensacola to Freeport, is steeped in history. Their landmarks, churches, museums, and forts are testaments to their unique heritage. Beyond their historical significance, these towns also offer a blend of tourist entertainment and coastal attractions, making them ideal vacation destinations. So, for those looking to explore some of Florida’s oldest-founded towns with plenty of activities, this list is a great starting point.

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