50 Historic Towns in Florida for Your Wander List!

Nov 11, 2021

50 Historic Towns in Florida for Your Wander List!
By Westgate Resorts

The 50 Best Historic Towns in Florida

If you love warm weather, day trips from Orlando, beaches, world-renowned amusement parks, and tropical relaxation, Florida is probably already high on your list of travel destinations. Some travelers are content to lie in the sun with a mojito or margarita in hand, while others live for the moment they can watch their kids’ faces light up at the sight of Mickey Mouse or the world of Harry Potter. Others still might be looking for educational vacation ideas or be curious about the fascinating history of the state.

Historic Towns in Central Florida

If you are visiting the Central Florida homeland of Disney, you are definitely in the right spot for quaint and cozy towns that brim with history and mystery. If you’re a history buff or lover of things from the past, keep reading as we dig into the 50 best historical towns in Florida and point you in the right direction so you can enjoy the amazing spots.

1 | St. Augustine | There’s no better town to open this list with than Florida’s oldest. St. Augustine was originally founded in the year 1565, and it is remarkably well-preserved. Spanish-style architecture can be found in abundance, alongside important historical sites like Castillo de San Marcos. Don’t forget to go on a ghost tour.

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2 | Fernandina Beach | The history of Fernandina Beach is so complex that it is commonly known as the Isle of eight flags in reference to its rule under the French, Spanish, English, Spanish again, Patriots, Spanish for a third time, Mexicans, Confederates, and finally Americans. If that seems confusing, don’t worry. A trip to the Museum of History should clear things up.

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3 | Tallahassee | Down for family road trip ideas? How about Tallahassee? Florida’s capital was chosen as a capital long before Florida ever became a state. The city was incorporated in 1825 and is home to a number of beautiful historical sites like St. Mark’s Lighthouse and the Mission San Luis de Apalachee, where you can enjoy displays of many interesting artifacts.

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4 | Quincy | The town of Quincy, named after the sixth American president, John Quincy Adams, gained its fame as a prosperous center for the then-booming tobacco industry. As a result of this wealth, a number of now-historic buildings were built that still stand and can be enjoyed today. It’s a must-visit for cigar lovers.

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5 | Jacksonville | Florida’s biggest city is also full of history. After Spain ceded Florida, locals named the area after Andrew Jackson. The city was officially incorporated in 1832. History lovers can enjoy a visit to Kingsley Plantation and the Riverside/Avondale historical district, where charming neighborhoods can be found.

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6 | Micanopy | As the oldest non-coastal town in Florida, the nickname “the little town that time forgot” is an apt description. Old-timey shops line the downtown area, making it a great place to wander and shop. The town is also known for its preservation of the history of the Seminole tribe. Huffington Post called it one of the “Cutest Small Towns in America.”

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7 | Apalachicola | If you find yourself in North Florida’s “Forgotten Coast,” stop by the small fishing village of Apalachicola. Here you’ll find more than 900 historical sites, including cute little cottages and beautiful old churches. The town prides itself on being quiet and charming, preserving the feel of Old Florida. The beaches are some of the quietest and most relaxing in the state.

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8 | Key West | When Commander Matthew Perry placed the American flag onto the island of Key West in 1822, he claimed it for the United States. Six years later, it officially became a part of Florida. You can still see the remnants of the beautiful town’s beginnings almost 200 years later.

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9 | Marianna | Founded in 1828, Marianna was named after the wife of its Scottish founder and her friend, Mary and Anna. Today, Marianna is best known as the site of a small but important battle in the American Civil War. The site of this decisive Confederate victory can still be visited today.

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10 | Pensacola | The original settlement at Pensacola predates even St. Augustine, though it didn’t last very long. Modern Pensacola was established in 1821, and five different flags have ruled over it. The Pensacola Lighthouse and Museum, the Historic Pensacola Village, and National Naval Aviation Museum make this a history buff’s paradise.

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11 | Cedar Key | Florida’s second-oldest town is out of the way, but well worth a stop if you find yourself in the Keys. With less than a thousand permanent residents, Cedar Key has retained its classic charm by avoiding development and maintaining its old buildings. The island started as a key port for cedar trees. Later, it became the western station of the Florida Railroad. Consider staying at the Island Hotel, which began as a general store in 1859, and don’t forget to kayak to the ghost town on Atsena Otie Key.

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12 | Sebring | Racing enthusiasts should make time for a stop in Sebring, home of the Sebring International Raceway. This track was built on a former airbase in 1950 and hosted the 1959 Formula One United States Grand Prix. The history continues today with the 12 Hours of Sebring, an annual sportscar race.

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13 | Avon Park | In 1884, English settler Oliver Crosby moved to Avon Park from New England to study the flora and fauna of the region. Not long after, another English settler convinced him the area resembled Stratford-Upon-Avon, a town in England that was the birthplace of Shakespeare. Thus, Avon park was born. Today it is known for the World War 2 bombing range that you can still visit.

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14 | Brooksville | Originally known as Melendez, Brooksville was founded in 1845. It is best known for Fort DeSoto, an 1840 military base established as protection against local native tribes. It was abandoned shortly afterward, as it was exceedingly difficult to bring in water. Today you can visit Fort DeSoto Park to learn about its history and see the beautiful natural sights.

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15 | Dunnellon | Dunnellon contains the ideal blend of historic sights and natural wonders. Rainbow Springs State Park offers incredible hiking and boating, and when you’re through with your visit, you can return to downtown Dunnellon’s historic district for a blast from the past.

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16 | Everglades City | Locate southeast of Naples, Everglades City is known as the gateway to Ten Thousand Islands. It is best known for its proximity to the everglades, but the old town is a great place to learn history too. The Rod & Gun Club, for instance, was frequented by hunters and fishers like Hemingway and Eisenhower.

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17 | Punta Gorda | The relaxing city of Punta Gorda has a recently restored historic district full of gorgeous old-style architecture. Of particular note is the A.C. Freeman House Museum built in a Victorian-style home. A stroll along the Harborwalk and the Fisherman’s village is also essential.

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18 | Winter Garden | If you have the time and energy after visiting the theme parks in Orlando, make a stop at the charming town of Winter Garden. The historic downtown offers a taste of Florida’s yesteryear, and there are numerous art galleries and theaters offering live events. It is also well known as a cyclist’s paradise.

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19 | Delray Beach | USA Today called Delray Beach “The Most Fun Small Town in America,” and it isn’t hard to see why. Atlantic Avenue is the longest main street in Florida, and there are endless things to do and see including food, art galleries, and historical buildings. Art lovers will enjoy the Delray Beach Art Trail.

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20 | Venice | Venice offers one of the best beach destinations in Florida, featuring 14 miles of beautiful coastline. It is so named for the Italian-style architecture, which contrasts with the Spanish style found in much of Florida’s historical towns. Natural history lovers will enjoy searching for unique shells and shark tooth fossils.

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21 | Mount Dora | Often considered one of Florida’s most beautiful towns, Mount Dora is a paradise for both nature and history lovers. It started as a small lakefront town in the 19th century, but it became popular in the 1920s. Enjoy old clapboard houses and the winter retreats of famous figures like Calvin Coolidge, Dwight Eisenhower, Henry Ford, and Thomas Edison.

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22 | Flagler Beach | If you are traveling between the more famous towns of Daytona Beach and St. Augustine, consider a stop at the retro town of Flagler Beach. Of particular note is Bulow Plantation Ruins Historic State Park, which documents the history of sugar plantations in eastern Florida.

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23 | Vero Beach | Vero Beach is home to a wide variety of locals, from billionaires to working-class people. As a result, it is rich in modern diversity. You can still visit the house of the city’s founder, Henry T. Gifford, which is located near City Hall. Vero Beach is notable as a stop along the late 19th century’s railway from northern Florida all the way to Key West.

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24 | Fort Myers Beach | If you are into watersports like kayaking or parasailing, you might have heard of Fort Myers already, as it is known as a hotspot for these fun activities. The fort that gives the city its name was one of the initial bases of operations for soldiers in the Seminole Indian Wars.

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25 | Fort Pierce | USA Today called main street in Fort Pierce one of the “Most Idyllic and Historic Main Streets in America.” The main attraction of the city’s beautifully classic Spanish Architecture is Sunrise Theatre, which first opened in 1924, where you can still see performances today.

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26 | Milton | Before the Second World War, Milton was the most industrialized city in the entire state. The strategic location of the Blackwater River made it a central hub for the flow of goods like bricks and lumber. Learn about the many shipwrecks that have occurred along the river, then go attend a show at the Imogene Theater, founded in 1912 after a fire destroyed much of the town.

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27 | Port St. Joe | Port St. Joe is popularly known as the “small town with a big heart.” Located along Florida’s Emerald Coast, this is a great spot to relax and enjoy beautiful unspoiled scenery. History lovers can learn about the early days of Florida, as this town is the home of the state’s constitution. Antique shops along the downtown area offer a glimpse into yesteryear.

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28 | Amelia Island | Some of Florida’s most unspoiled beaches surround Amelia Island, where Spanish moss grows along the stunning coastline. The oldest saloon in Florida calls the townhome, and it is listed in the National Register of Historic Places alongside many other local landmarks. This town is also located just a short carriage ride away from the historic town of Fernandina Beach.

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29 | Gainesville | The city of Gainesville’s Historic Thomas Center offers local history exhibits, art galleries, and period rooms, but there’s far more to the city. Follow your visit with a trip to the A. Quinn Jones Museum and Cultural Center to learn about the civil rights icon. Punk music fans should time their visit around The Fest, an annual October music festival.

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30 | Steinhatchee | Victorian-style homes make visiting this fishing village feel like stepping into the 19th century. The scenery has a lot to offer nature lovers as well. A wide variety of wildlife lives in the area, which also offers some of the best fishing in the state. If you find yourself in the Big Bend region, it is well worth a stop.

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31 | Cortez | Cortez is arguably one of the last truly authentic fishing villages in Florida. Not only is it a gorgeous place to hike and soak up the sun, but the old-school, small-town charm is remarkably preserved. No visit to Cortez is complete without a visit to the Florida Maritime Museum, which is located inside a former schoolhouse from 1912.

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32 | Quincy | West of Tallahassee lies the old city of Quincy, which features Victorian homes and a thriving arts scene. Quincy’s downtown square, which centers around the historic Gadsden County Courthouse, is home to a variety of old buildings, including a classic drug store.

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33 | Briny Breezes | If you find yourself near Palm Beach County, make a stop at Briny Breezes to visit the only oceanfront trailer park in Florida. Founded in 1919 by Ward Beecher Miller, it originally served as a place for him and his family to raise turkeys and dairy cows. Later, he let people park their trailers on his land for three dollars a week during the great depression.

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34 | Captiva Island | Not far from Fort Myers, Captiva Island is an outdoorsman’s paradise. Fishing, boating, biking, and hiking are all popular activities here. After your active day is through, visit the History Gallery curated by the Captiva Island Historical Society for a trip back in time.

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35 | Sopchoppy | This town’s strange name is somehow less strange than what it’s known for. Charles Kuralt, a newsman, originally brought attention to Sopchoppy in 1972 with his story about the local tradition of “worm gruntin,” where residents used an iron bar and wooden stake to shake the ground and annoy worms into surfacing. Visit in April to attend the Worm Gruntin’ Festival.

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36 | Fanning Springs | Fanning Springs is known for two popular destinations. The first is Fanning Springs State Park, a beautiful park along the shores of the Suwannee River. The other is Fort Fanning, a Second Seminole War fort that has since been turned into a museum.

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37 | Sanderson | North of Gainesville, Sanderson is known as the gateway to Olustee Battlefield Historic State Park. This site commemorates the largest civil war battle in Florida, where over ten thousand troops battled for five hours in a pine forest. Visitors can stroll through the park and learn about what took place that day. A reenactment is held each February.

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38 | McIntosh | This tiny town has a population of less than 500, but it is well worth the visit if you are in the Gainesville area. Sixty different structures all qualify as historic buildings, including churches, homes, and a train depot.

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39 | Waldo | Waldo’s historic cemetery contains the remains of many African American pioneers, including Henry Hill, the city’s first black fireman, as well as many veterans of the civil war. A trip to Waldo should also include a stop at their famous Antique Village.

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40 | Naples | Situated in Florida’s southwest region along the Gulf of Mexico, Naples is one of the most picturesque towns in the state. The historic downtown area features many art galleries and antique shops to peruse as you enjoy the scenery.

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41 | Lakeland | If you love history, a trip to Lakeland is worth it just for a trip to the Polk Museum of Art, but there is far more to the town. Hillis Garden offers a variety of plant life, and Lake Mirror Park is the perfect spot for an evening stroll.

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42 | Sanibel Island | This island in the Gulf of Mexico is a popular destination for shellers. The beach is absolutely covered in a variety of shells, so natural history lovers will be delighted to make significant additions to their collection. The island also offers boating, fishing, and beachfront relaxation.

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43 | Key Largo | Classic film buffs might recognize this town as the titular setting of the 1948 noir film starring Humphrey Bogart and Lauren Bacall, but this gorgeous Key island has lots more to offer than film history. Not only is it located near multiple state and national parks, but it is the self-proclaimed Dive Capital of the World.

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44 | Islamorada | This village is comprised of six islands south of Miami, and it is truly a tropical paradise. Dolphin encounters, fossil searching, and diving are all popular activities. Indian Key Historic State Park is also nearby, where you can see the site of a lucrative business that salvaged shipwreck cargo.

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45 | St. Petersburg | St. Petersburg is one of the biggest and most famous cities on this list, and for good reasons. Art lovers can see classic works by Dali and Chihuly, then top it off with trips to famous beaches. It’s also easy to combine a trip to St. Petersburg with one to Fort DeSoto Park to see the fort from the Spanish-American war.

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46 | Coconut Grove | Coconut is a part of Miami, but it has its own distinct flare. History lovers will likely be most drawn to the Renaissance-style architecture of Vizcaya Museum and Gardens, the former estate of famous businessman James Deering. Visitors will also enjoy a variety of live entertainment and a thriving art scene.

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47 | Dunedin | West of Tampa along the Gulf Coast, Dunedin has miles of gorgeous waterfronts that compliment a wide selection of history and culture. Dunedin is also a paradise for beer lovers, with lots of breweries calling it home.

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48 | Tarpon Springs | Unlike the Spanish influence found in most of Florida, Tarpon Springs is known for its Greek heritage. More than 10% of its permanent residents have Greek heritage, more than any other city in the country. It’s also known for being the “sponge capital of the world,” and visitors can learn about the long history of sponge diving here.

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49 | Dade City | Less than an hour northeast of Tampa, Dade City is best known for the Pioneer Florida Museum, which allows visitors to examine state history over sixteen acres. If you visit during the annual Pioneer Days Festival, you can enjoy the past coming to life in the present.

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50 | Matlacha | Just off the coast of Ft. Myers lies Matlacha Island, a hidden gem famous for its fishing. The island is also known for being covered in bright, tropical art. True Tours of Ft. Myers offers a tour known as Flavors of Matlacha, and if you take part in it, you’ll learn all about its history of drug running, traveling carnivals, and much more.

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Last Tips on the 50 Best Historic Towns in Florida

The Sunshine State brims with history and mysteries of the past making it both the perfect educational vacation spot with more than enough things to stack your itinerary. No matter where your map takes you, you will be in for an adventure around every corner. To learn more about other exciting vacation destinations, check out our Travel Blog for tips, tricks, and things to do in your favorite getaway places.


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* Westgate Resorts is in no way affiliated with the attractions featured in this article. Items or places listed are current as of the publishing date of this article. Please call or visit the respective website for the most up-to-date offerings and details.