The Best Small Towns in Florida to Chill Out In 2024

A relaxing escape to Florida guides visitors away from urban attractions and into historic communities and waterfront towns, home to some of the Sunshine State's most pristine natural beauty. The best small towns in Florida to chill out in 2024 are well-preserved, sparsely populated destinations where travelers can disconnect and distance themselves from overwhelming city hassles like traffic, advertising, pollution, and overpriced tourist experiences. While some of the best small towns to chill out are secluded island escapes with crystal-clear, untouched waters like St. George Island, others are lush, mountainous communities that add a unique twist to the typical Florida beach escape.

Montverde

As its name suggests, Montverde is a lush, mountainous town where visitors can immerse themselves in calming, untouched nature, such as preserves, forests, and parks. In the heart of Florida’s rolling hills, Montverde offers a tranquil retreat for those seeking to escape the hustle and bustle of city life. The town is a haven for nature lovers, with its pristine landscapes providing ample opportunities for hiking, bird-watching, and exploring the great outdoors. Must-see attractions in Montverde include the Green Mountain Scenic Byway, Lake Apopka, and Truskett Park, which is home to the oldest houses in town. Complementing the relaxing natural appeal is a vibrant culinary scene, with some of the most iconic dining spots being Mr. Willie's Grill and Black Bear Kitchen.

Crystal River

Crystal River is the perfect chill-out spot for nature enthusiasts for its preserves, parks, and fishing hotspots. In addition to its clear waters, relaxing ambiance, and endless outdoor activities, Crystal River offers unique experiences, such as being the only place in North America where you can legally swim with manatees. Travelers visiting Crystal River can embrace the city’s founding history by visiting its heritage village, which is dotted with preserved remnants of homes and old local businesses like the Franklin Anderson Gallery and The Cotton Club, a famous gift shop in town. Though a calm environment and nature-centric escape are some of the town’s main characteristics, events and community gatherings also play a significant part in the small-town experience. Year-round events can enhance your visit to Crystal River, with some of the most popular being the Florida Manatee Festival, Pine Street Jam & Parrothead Party, and the Ozello Craft Show and Chili Cookoff.

Mount Dora

Nicknamed the Festival City for its engaging community scene, Mount Dora sits just a short 20-mile drive from Montverde. This small town is the perfect place to chill out for those seeking a blend of social vibrancy and natural beauty. Known for its lively atmosphere, attractions, and artistic edge, Mount Dora is home to renowned galleries and the world-class Mount Dora Art Festival, making it an ideal destination for escapers who appreciate both culture and nature. The small-town experience in Mount Dora is highlighted by its history, endless natural attractions, and unique artistic experiences like the Modernism Museum. Highlights of any well-rounded visit to Mount Dora include attending some of the town's popular events like Art in the Alley and exploring hidden community gems like Renninger’s Antique Market for antiques and collectibles. Additionally, Mount Dora is home to a quaint selection of lodging options, with some of the top-rated being nature-centric cabin rentals like the Oaktree Cottage or the vibrant Victoria Rose Estate. For a more memorable experience, visitors can plan their stay at the Lakeside Inn in Mount Dora, which dates back to the early 1800s.

Naples

Naples adds an upscale ambiance to the typical natural escape and is widely recognized as a premier resort town. It’s a favorite among golf enthusiasts, boasting over 90 golf courses, including world-class options like Tiburón Golf Club and Arrowhead Golf Club. Adding to the town's natural and athletic appeal is a vibrant shopping scene featuring everything from designer luxury brands to charming mom-and-pop stores in the downtown area. The main central shopping district to visit for some retail therapy is Third Street. While many of the best small towns to relax in Florida are secluded, nature-centric escapes, Naples is a popular vacation spot for those prioritizing a touristic scene and a lively ambiance. Better yet, a visit to Naples is incomplete without embracing the town’s vibrant culinary scene, with some of the best-rated dining spots being M Waterfront Grille, the Tavern at Mediterra, and Osteria Tulia.

St. Augustine

St. Augustine, known as the oldest continuously inhabited European-established settlement in the United States, is an ideal relaxing getaway for its contrast of natural and cultural attractions. The town boasts many well-preserved remnants from past times, including forts and Instagram-worthy home designs of Spanish Renaissance Architecture. Despite its rich heritage and thriving tourist scene, St. Augustine, like many of Florida's best small towns to chill out, offers an abundance of nature, including beaches, parks, and more. Notable natural spots include Anastasia State Park, St. Augustine Beach, and the St. Augustine Wild Reserve. In addition to its natural beauty, St. Augustine also features unique attractions such as the Fountain of Youth, dating back to the early Spanish settlers' period, and the Pirate & Treasure Museum, which tells the story of the town's history as a significant port. This combination of natural and cultural experiences makes St. Augustine a standout destination for relaxation and exploration.

Cedar Key

The artistic colony of Cedar Key is one of the best small towns in which to enjoy a vibrant community scene that embraces local talents through events, small businesses, and more. Originally a fishing village, Cedar Key's main street, Dock Street, features local dining, art galleries, and shops. It is the perfect place to zone out into small-town charm. Events like the Cedar Key Arts Festival and the Cedar Key Small Boat Meet, held in May, are among the town's most notable and attract many tourists. The town's tranquility is reflected in its historic sites and natural beauty, like Cedar Key Scrub State Park and protected wildlife preserves. Visitors seeking insight into the town's creative side cannot miss the many galleries and displays, including the Cedar Key Arts Center and the Cedar Keyhole Artist Co-Op, which showcase an array of local talents, from glass and leather arts to paintings and abstract sculptures.

Apalachicola

Apalachicola, a charming small town on Florida's Gulf Coast, is widely recognized for its historic appeal, with well-preserved architecture and buildings like the Coombs House Inn, Dixie Theatre, and the vibrant Gibson Inn, which is built in Cracker-style architecture and is a perfect example of societal preservation in the town. Adding to the town's allure, Apalachicola is an iconic fine dining destination for foodies. Its fresh seafood, particularly oysters, can be enjoyed at local eateries and festivals like the Florida Seafood Festival, which is a crucial element of the small-town experience in Apalachicola. Additionally, those looking to enjoy both community engagement and natural enchantment will appreciate the town’s proximity to the Apalachicola National Forest and other small communities that make an excellent destination to chill out in Florida, like St. George Island, which is known among locals as the perfect family escape.

St. George Island

St. George Island is the definition of a secluded beach escape and is best recognized across the Sunshine State as a hub for untouched waterfront paradise. With its pristine, white-sand beaches and crystal-clear waters, it offers an idyllic retreat for those looking to unwind and reconnect with nature. The island's natural beauty is complemented by its charming local amenities, including cozy beachside cottages, fresh seafood restaurants, and vibrant local markets. One of the town’s most prominent attractions is St. George Island State Park, a pristine natural reserve featuring miles of untouched beaches, hiking trails, and picnic areas. The community element also plays a significant part in the town's tourist appeal as one of the best small towns in Florida to chill out in 2024, with one of the town's most popular events being the Chili Cook-Off in March. Smaller gatherings, such as the St. George Island Farmers' Market held twice a month, also contribute to the island's lively and welcoming atmosphere. These events, along with natural attractions like St. George Island State Park complemented by top-notch dining experiences such as the Blue Parrot Oceanfront Café, highlight the island's appeal as a peaceful, refreshing getaway.

Choose Your Ideal Floridian Retreat

Ultimately, the best small towns to chill out in Florida offer a delightful escape from city life, whether it be through an upscale wellness retreat in Naples or connecting with untouched nature in Cedar Key. These destinations provide a perfect blend of relaxation and local character. Choose the most appealing option for your next getaway, or explore more than one side of the Sunshine State with the perfect town-hopping itinerary through communities of close proximity, like Crystal River, Montverde, and Mount Dora.