Florida ranks highly as a prime destination for road trips, offering a wealth of scenic landscapes, delightful dining, charming boutiques, and quirky roadside attractions. Anyone with a few days to spare and an adventurous spirit can find something to enjoy here. We’ve previously shared various routes, from the Ultimate Central Florida Road Trip to a spine-tingling journey through the state’s eerie haunted spots. However, the true essence of Florida shines in its picturesque small towns, which invite explorations of nature and diverse cultures while showcasing the state’s rich history. This carefully curated road trip promises to make your next getaway or weekend break truly memorable. Discover some of Florida’s most enchanting small towns—all in one amazing adventure.
1. Cedar Key
Cedar Key, located in Levy County, is a charming, traditional fishing village renowned for having some of the finest clams not just in Florida, but arguably across the globe. Visitors can immerse themselves in the area’s natural beauty, teeming with diverse wildlife, or enjoy leisurely walks along the picturesque streets filled with quaint shops and delightful eateries. For a truly unique experience, consider booking a stay at the Cedar Key Bed & Breakfast, a lovely Victorian-style establishment that exudes a whimsical charm reminiscent of a life-sized dollhouse.
Address: Cedar Key, FL
2. Crystal River
Nestled along Florida’s Nature Coast, this charming town is renowned as the prime destination for encountering manatees, whether you’re looking to observe them in their natural habitat or even take a swim alongside these gentle giants. In addition to its manatee attractions, the town boasts a range of historic architecture and serene parks, making it a perfect getaway for families. For a memorable and budget-friendly accommodation option, consider staying at King’s Bay Lodge, where the friendly staff will assist you in organizing all the activities you want to explore during your visit.
Address: Crystal River, FL
3. Tarpon Springs
Next, we’re heading south to a charming town that seems to belong to a different era. Tarpon Springs, a coastal Greek enclave located in Pinellas County, is renowned for its picturesque sponge docks. Historically, this town attracted affluent winter visitors, so take a leisurely drive through its historic district to admire the stunning Victorian architecture. Pro tip: Be sure to stop by the Hellas Restaurant to savor the delicious Greek dishes that the area is celebrated for. And don’t forget to grab some delectable treats from the local bakery before you leave!
Address: Tarpon Springs, FL
4. Mount Dora
As soon as you arrive in this charming town in Central Florida, you’ll likely find it quickly becomes one of your top picks. Renowned for its fantastic shopping scene, particularly when it comes to antiques, this destination offers a delightful experience for vintage enthusiasts. A visit wouldn’t be complete without a stay at the historic Lakeside Inn, Florida’s longest-operating hotel, which has been welcoming guests for over 130 years. For those with a passion for classic trains, consider booking a journey on the Orange Blossom Cannonball — a nostalgic ride aboard a wood-burning steam locomotive that whisks you back to a bygone era.
Address: Mount Dora, FL
5. DeLand
As we journey further east, our next destination is the charming town of DeLand in Volusia County. Take a leisurely walk through the downtown area, filled with quaint boutiques, antique shops, and delightful eateries. Immerse yourself in the stunning murals and historic architecture that contribute to the town’s distinctive appeal. For nature enthusiasts, a refreshing swim at the nearby De Leon Springs State Park is a perfect way to enjoy the outdoors. A must-see is the breathtaking Stetson Mansion, which holds the title of Florida’s first luxury residence.
Address: DeLand, FL
6. St. Augustine
Finally, we arrive at St. Augustine, the oldest city in the United States. Here, you can discover the impressive Castillo de San Marcos, stroll through the quaint cobblestone streets filled with a variety of shops and eateries, and immerse yourself in the rich history at numerous museums and heritage sites. Don’t miss the pristine beaches of Anastasia Island State Park, where you can relax in the sun. For those intrigued by the supernatural, St. Augustine is renowned for its haunted reputation. Consider joining a ghost tour for an entertaining glimpse into the city’s eerie past.
Address: St. Augustine, FL