9 Quirkiest Florida Towns To Visit In 2025

With over 8,400 miles of shoreline, there is no debate that Florida is one of the best beach destinations in the country. However, you may not realize how quirky some of Florida’s small towns can be. Towns like Dunedin have a rich Scottish heritage, while other towns, like DeLand, are known for their skydiving scene. Whether you want to take to the sky or celebrate some of these towns’ European heritage, these nine towns will show you a more unconventional side of Florida.

Celebration

About a half hour from Orlando, travelers will find Celebration, a charming town founded by the Walt Disney Company in the 1990s. As you walk through town, you can marvel at its Southern-inspired architecture. Notable landmarks include the post office, which features a postmodern design, and the old town hall, which blends neoclassical and postmodern styles. For an extra-magical town tour, consider organizing a horse-drawn carriage ride with Misty Blue Acres. After the carriage ride, visitors can pop into Maple Street Biscuit Company for a signature chicken biscuit or chicken and waffles.

Crystal River

Crystal River is one of the few towns where visitors can swim with manatees. Manatee tours run year-round, with companies like Bird's Underwater Manatee Dive Center offering excursions in Kings Bay. Visitors can also spot manatees on a glass-bottom tandem kayak tour with Clear Kayaking Ecotours. Besides its manatees, the Crystal River area is home to one of the state’s most impressive archaeological sites: The Crystal River Archaeological State Park. Spanning 61 acres, this pre-Columbian site has temple and platform mounds, burial mounds, and a plaza area that once served as a ceremonial site for Native Americans.

Venice

Recognized as the “Shark Tooth Capital of the World,” Venice is known for the fossilized prehistoric shark teeth that can be found along its shores. There are several beaches around town where visitors can hunt for these shark teeth. Caspersen Beach is a popular option, featuring a short nature trail that winds through a coastal hammock. Travelers with dogs, meanwhile, can head to Brohard Paw Park, a pet-friendly beach where dogs are allowed off-leash. Anglers will enjoy a sunny afternoon at the Venice fishing pier, a 700-foot pier on the south end of the town's beach.

Cortez

As one of the few remaining fishing villages in the region, travelers will find plenty of water recreation in Cortez. Travelers can sign up for a pirate ship cruise with Pirate Adventures of Cortez, where they will board the Sea Gypsy IV, cruising the Palma Sola Bay, Anna Maria Sound, and Sarasota Bay. To try your luck at fishing, consider an excursion with GulfCart Fishing Charters, where you will have the chance to fish for grouper, snapper, redfish, tarpon, trout, and more. There are plenty of seafood restaurants to dine at as well, such as Swordfish Grill, which offers fresh seafood and live entertainment on the waterfront.

Dunedin

Although Dunedin is widely known for its white-sand beaches, it is also rich in Scottish heritage! Each year, the town celebrates this heritage during the annual Dunedin Highland Games, which features a day packed with Celtic flags, dancing, music, games, and good music. Travelers can further explore Dunedin’s history at the Dunedin History Museum, which has exhibits on the town’s origins, maritime history, citrus industry, and railroads. Bagpipers and Celtic drummers, meanwhile, frequent the Dunedin Marina around sunset. Visitors can also head to the marina’s commercial docks to book a fishing charter or dolphin cruise.

Tarpon Springs

Nicknamed “The Sponge Capital of the World,” Tarpon Springs has a rich sponge-diving heritage. Travelers can stop by the Tarpon Sponge Company, which sells natural sea sponges from the Tarpon Springs Sponge Docks, handy for cleaning, decorating, and bathing. The town has a strong Hellenic influence as well, largely expressed through its Greek restaurants! Grab a bite at Hellas Restaurant & Bakery, which has been serving Greek dishes for over half a century. One of the most distinctive natural parks to visit is Anclote Key Preserve State Park. Accessible only by boat, it is home to at least 43 bird species, including the bald eagle and the American oystercatcher.

St. Augustine

As the oldest continuously occupied settlement of European origin in the United States, travelers will find plenty of European influence in St. Augustine. The Castillo de San Marcos is the perfect example of this history, featuring a beautiful Spanish stone fortress that is over three centuries old. Travelers can also explore St. Augustine’s historic district via trolley on a tour with Old Town Trolley Tours, a hop-on, hop-off trolley service with live narration en route. Right across the street from the Castillo, visitors can grab lunch at River & Fort, which offers Southern-style dishes with fantastic bay views.

Steinhatchee

Steinhatchee is another prominent fishing town in Florida that is popular among anglers and scallopers. Scalloping is a great activity to try out with your family, with several charters around Steinhatchee offering excursions. Fin Action Charters is an excellent option, offering scalloping trips from June 15th and onwards this year, along with inshore fishing, manatee tours, and sunset cruises. Travelers wanting to explore the waters at their own pace can opt to rent a boat at the Steinhatchee Marina, which offers both boat and kayak rentals. For some fresh fish or crab following your day on the water, enjoy a meal at Kathi's Krab Shack, which serves a variety of fresh seafood straight off the boat.

DeLand

DeLand, known as the 'Skydiving Capital of the World,' is sure to give you a thrilling adventure. Those bold enough to take the leap can arrange an experience with Skydive DeLand, which has been leading skydiving experiences since 1982 and offers courses for all skill levels. Travelers who prefer to stay on solid ground have plenty to explore as well. Visitors can drive down to Blue Spring State Park, where they can bird watch, view manatees, camp, hike, and paddle. To experience a bit of DeLand’s art scene, stroll through the DeLand Sculpture Walk, which features sculptures from artists around the U.S.

Final Thoughts

With the heat of summer already underway, you may be planning your summer escape to some of Florida’s most beloved vacation destinations. However, for a quirkier trip, you should consider adding some of these towns to your itinerary, giving you the chance to see manatees, sail in pirate ships, and enjoy Greek cuisine. By the end of your trip, you might even have a whole new perception of the Sunshine State!