8 Delightfully Odd Towns In Florida
While most people travel to Florida to experience Disney World, marvel at the Kennedy Space Center, and relax at Miami's South Beach, some of the state's most intriguing attractions don't receive widespread media attention. It takes straying away from the famous highways and known tourist hubs to discover what makes Florida so delightfully odd. From the endless haunted spaces in St. Augustine to the undersea hotel in Key Largo, these unusual attractions give tourists something to look forward to on their return trip to the state.
Together, these hidden gems celebrate the state’s eccentric history, natural quirks, and creative spirit, inviting curious tourists for out-of-the-ordinary encounters. For those willing to wander off the beaten path, here are quirky towns in Florida that will transform an ordinary vacation into a story worth telling.
St. Augustine
St. Augustine accrued numerous peculiar personalities, landmarks, and experiences over four centuries of existence, making it one of the most delightfully odd towns in Florida. Visitors get immersed in the gruesome world of torture at the Medieval Torture Museum, where 6,000 square feet of interactive displays reveal the depths of depravity the human mind can sink to. The macabre inventory features bondage tools, execution methods, torture techniques, and other despicable tools employed by murderers from medieval days. The tour promises to leave a sour taste in the mouth, and a gift shop is available for guests who wish to purchase a souvenir.
St. Augustine's cobblestone streets are lined with historic buildings, such as the Spanish Renaissance Revival Ponce de Leon Hotel. This 19th-century landmark embodies Victorian opulence with elaborate architectural details, including a wraparound mural and Tiffany-stained-glass windows. It is also believed to be haunted by the ghost of a small boy. Furthermore, the St. Augustine Pirate & Treasure Museum documents the town's pirating heritage through eccentric relics, including one of the oldest treasure chests and actual shipwreck salvages.
Key Largo
Key Largo offers travelers their first experience of sleeping in an underwater hotel. This extraordinary adventure is available at Jules' Undersea Lab and promises intimate encounters with the diverse forms of life thriving beneath the ocean's surface. It is the world's only undersea habitat where scuba divers can experience what it's like to live and sleep 25 feet below the surface. The unique attraction also doubles as an educational experience, offering behind-the-scenes views of majestic marine species through a pane of hardened glass.
Additionally, Dolphin Life Key Largo welcomes animal lovers to swim with dolphins and enjoy intimate interactions. The fascinating facility rescues dolphins and whales in need, providing a safe refuge and educating visitors on how to care for the animals. Those who wish to venture into the open sea can book a tour with Key Largo Princess Glass Bottom Boat for an unforgettable cruise on a luxury yacht with glass bottoms, through which passengers can see whatever is happening under the water.
Hallandale Beach
Hallandale Beach is home to the second-tallest statue in the continental USA after the Statue of Liberty. The Pegasus and Dragon Statue is a breathtaking spectacle straight out of a Greek novel. It rises 110 feet above Gulfstream Park and weighs about 715 tons, depicting the battle between Pegasus and the dragon from Greek mythology. The bronze statue, designed and cast by a German bronze foundry, has become a defining landmark in Hallandale Beach. Tourists can be found trying to snap the best selfie in front of the spectacle.
Hallandale Beach is also known for its sandy Atlantic Coast beaches, and vacationers who fancy a soak can head to South City Beach Park. This low-key stretch of sand allows people to swim and soak up the sun, while offering amenities such as sand volleyball, a shaded pavilion, and picnic areas. Lastly, don't miss out on the vibrant nightlife at Amsterdam Night Club Hallandale, characterized by infectious energy, booming music, neon-lit surroundings, Mediterranean cuisine, and hookah.
Lake Wales
Curious tourists from across the United States come to this Polk County location to witness and probe the mystery of Spook Hill. This historic gravity hill has long fascinated the public with its gravity-defying phenomena, making it a significant attraction. A car parked in the neutral gear at the bottom of the structure seems to roll up, confusing spectators. According to local folklore, horses transporting people in the past found it difficult to ascend it. Although this is an optical illusion, it never fails to intrigue visitors and leaves them searching for a logical explanation.
Visitors in Lake Wales on the weekend can enjoy a fun shopping experience at the Sunshine Flea Market. The market draws dozens of vendors and features a broad selection of products, including local produce, second-hand clothing, vintage furniture, jewelry, and other collectibles. Meanwhile, adventure seekers can escape to Lake Kissimmee State Park for camping, hiking, fishing, and wildlife watching activities across a 5,930-acre untamed habitat of forest, prairie, flatlands, and lakes.
Key West
Popularly known as the southernmost destination in Florida, Key West has a walkable Old Town district with a series of enduring landmarks, and Captain Tony's Saloon is arguably the most intriguing. Apart from being one of the state's oldest pubs, it was once a morgue, and this dark side of its history remains with it to this day. Visitors drinking at the venue can see gravestones and a hanging tree, with corpses believed to be buried under the bar's floor. While the thought of the horrors that once occurred at the site can be upsetting, they don't stop patrons from having a good time with delicious cocktails or from dampening the carnival atmosphere.
Key West is also home to the Truman Little White House, where America's 33rd president used to spend his winters. The 19th-century mansion houses rare relics and memorabilia that shed light on Truman's legacy and its role as a command station during several American wars. Don’t forget to hit the beach before leaving Key West. Smathers Beach is the largest in town, offering miles of sandy shoreline, a string of shady palm trees, and calm, shallow waters for vacationers to enjoy.
Winter Park
This artsy suburb of Orlando invites fans of the quirky and odd to explore a fascinating collection at Prometheus Esoterica. This eccentric establishment in Winter Park specializes in esoteric teachings and alternative healing methods. Its display space features an inventory of peculiar items, including grinning skulls, taxidermy specimens, macabre items, obscure books, and other oddities that may disturb guests. The venue is regarded as a sanctuary for individuals seeking spiritual and mystical experiences for enlightenment and personal growth.
Those drawn by the arts can witness Winter Park's artistic side at the Blue Bamboo Center for the Arts. This intimate performance stage accommodates approximately 100 audience members and features thought-provoking spoken-word presentations, live music, dance routines, and visual arts in a family-friendly setting. Meanwhile, the Winter Park Farmers’ Market is the perfect blend of community and commerce. Guests can take advantage of its infectious vibe to buy a variety of local products, including baked goods and produce, and to converse freely with residents to learn about their culture.
Williston
Williston is an eco-tourist's paradise on Florida's Nature Coast, renowned for its prolific snorkeling and scuba diving spots. However, it is best known for Devil's Den, a prehistoric sinkhole that feels like a portal to another universe. Diving into the hole reveals a 54-foot underwater cavern with see-through spring waters, believed to have formed eons ago. The water maintains a comfortable 72 degrees temperature at all times, inviting holidaymakers to discover impressive stalactites, ancient crystalline formations, and other fossils.
Williston is full of oases that characterize its stunning natural scenery, such as Cedar Lakes Woods and Gardens. Here, nature lovers can explore over 50 manicured gardens, waterfalls, koi ponds, and other breathtaking landscapes. Meanwhile, visiting families can have a blast at Kirby Family Farm. This educational and entertainment center features a railroad museum. It offers an array of fun activities for the whole family, including old-car rides, a train ride, live music, amusement rides, and notable appearances by celebrity guests.
Crystal River
Crystal River is one of the few places in Florida where vacationers can swim with manatees. This once-in-a-lifetime experience is provided courtesy of Crystal River Manatee Tours, which organizes snorkeling tours for guests to interact intimately with the gentle sea cows in their natural habitat. These fun excursions are perfect for family getaways, taking them on a river safari down the Gulf of Mexico, offering a unique chance to witness the gentle beasts' behavior.
However, those who want to admire the animals without getting into the water can visit Three Sisters Springs. This magical park is famous for its crystal-clear turquoise waters, through which you can watch the manatees swimming during an easygoing paddling session. Art lovers can set aside a few minutes to examine a display of crafts and art by local artists at the Franklin Anderson Gallery of Arts, featuring pottery, woodwork, jewelry, sculptures, and paintings.
From petting gentle sea cows underwater in Crystal River to exploring mystical artifacts in Winter Park, these bizarre towns in Florida transform ordinary vacations into unforgettable adventures filled with surprise and charm. By stepping beyond theme parks and beaches, travelers uncover stories, traditions, and attractions that feel wonderfully unexpected. These offbeat destinations reward curiosity with lasting memories, proving that Florida’s true charm lies in its quirks and inviting visitors to return with a fresh perspective on the state.
