12 Picturesque Small Towns in Florida for a Weekend Retreat
Beautiful year-round weather, picturesque beach scenery, and luxurious seaside resorts make Florida one of America’s most touristy states. It is no surprise that more than 100 million visitors, both domestic and international, come to experience the Sunshine State each year. Beyond the world-class amusement parks in Orlando and the buzzing nightlife in Miami, Florida is home to charming small towns offering an escape from the rowdy crowds and presenting the ideal setting for a lazy weekend.
From historic coastal villages and artsy communities set amidst scenic natural surroundings to hidden riverfront locales, they have a laid-back atmosphere that lets you break away from the hustle and bustle of the city. This presents an excellent opportunity to discover historic downtowns, experience unique cultural heritage, and explore underrated state parks for a memorable experience. So, if you are up for a weekend of relaxation, rejuvenation, and restoration, these gorgeous small towns in Florida promise all that and then some!
St. Augustine
An immersive historical experience awaits tourists in America’s oldest city! With a legacy dating back to the 16th century, St. Augustine provides a captivating journey to the nation's formative years. Exploring its quaint downtown feels like stepping into a time capsule, with colonial Spanish architecture dominating the streets. There is a treasure trove of historical gems to experience, starting with the Castillo de San Marcos National Monument. This historic fort has stood for over three centuries, built by the Spanish to protect Florida from pirates and hostile forces. You will also come across the St. Augustine Pirate & Treasure Museum, home to a vast collection of unique pirate artifacts, including a 17th-century treasure chest.
Exploring all the historic sites in St. Augustine might take more than a few days, but for a change of pace, consider visiting the St. Augustine Alligator Farm Zoological Park. The park is home to over 20 species of crocodilians, as well as a variety of birds and mammals, leaving visitors in awe. Alternatively, Anastasia State Park showcases the beauty of the town's natural surroundings, offering stunning views of Matanzas Bay. After a long day of exploration, remember to enjoy a luxurious lodging experience at the Hilton St. Augustine Historic Bayfront.
Monticello
This charmingly small community in Jefferson County delights visitors with its artsy vibe and easygoing atmosphere. Locals appreciate and support the arts at various venues around the town, including the Monticello Opera House. The 1890 theater sits in the heart of the historic downtown, entertaining audiences with plays, concerts, musicals, and other live performances. Additionally, Monticello Ecological Park, with its richly diverse ecosystem, invites nature lovers to wander scenic trails and spot over 30 bird species, including warblers, turkeys, and owls.
In Monticello, the Jefferson Recreation Department offers numerous outdoor activities for visitors, ranging from hiking to picnicking and sports. For an adrenaline rush, consider the Historic Monticello Ghost Tours, which guide you through the town's haunted spots. Later, you can spend the night at the historic Denham Inn for a rustic accommodation experience.
Silver Springs
This ecological paradise in northern Florida boasts unparalleled views of clear underground waters flowing from nearly 30 springs within its area. The town is renowned for Silver Springs State Park, often dubbed as Florida’s first tourist attraction. Travelers take laidback boat rides on crystal clear waters surrounded by stunning natural beauty. Within the park, the Silver River Museum & Education Center offers captivating exhibits of fossils, artifacts, and taxidermy showcasing Florida's paleontology, archaeology, and natural history.
The Juniper Springs Recreation Area offers more recreation opportunities, including swimming in pristine spring waters. It also hosts the Juniper Springs Campground for those looking for the ultimate outdoor experience amidst the Ocala National Forest. Lastly, you will find lovely accommodation at the OYO Hotel Mustang to relax for the night.
Marathon
This picturesque island escape in the Florida Keys is renowned for its stunning beach scenery and relaxed atmosphere, making it ideal for a weekend getaway. There are numerous beaches, but many tourists find themselves at the sandy Sombrero Beach, a great place to lounge on the shore, sunbathe, or dip in the toasty waters. Wildlife enthusiasts will enjoy exotic animal encounters at the Dolphin Research Center. The center features a series of saltwater lagoons, providing habitats for dolphins and California sea lions.
Additionally, history buffs and aircraft enthusiasts will appreciate a visit to the Marathon Air Museum. This small yet delightful facility exhibits several classic planes, photographs, and other archives related to the aviation industry. For accommodations, consider staying at the Hampton Inn Marathon.
Naples
Despite its small size, Naples is a major tourist destination, boasting an array of attractions. Visitors enjoy world-class shopping, high-end waterfront resorts, and a respected arts scene. The 170-acre Naples Botanical Garden is a tropical oasis housing diverse plant life that nature lovers will enjoy exploring. Meanwhile, the historic Naples Pier offers panoramic Gulf views and activities like bird-watching, sunsets, and dolphin spotting.
Shoppers will appreciate the premier downtown commercial district, which features a mix of renowned boutiques and restaurants. Don't miss the opportunity to browse the shops at Tin City Waterfront. Nature enthusiasts can also visit the Naples Zoo at Caribbean Gardens to see a variety of animals. With its beaches, resorts, arts scene, shopping, and natural beauty, Naples offers something for every visitor, including a remarkable stay at the Hilton Naples.
Winter Park
Winter Park offers visitors a culture-rich experience in a quaint setting, surrounded by lush nature. It is famous for its outdoor spaces, allowing you to enjoy Mother Nature’s endless bounty. A prime example is the Mead Botanical Garden, which will awaken your senses with beautiful sights, sweet smells, and soothing sounds. The park offers laid-back nature trails traversing beautiful flower gardens and wildlife habitats that are a joy to explore. Art connoisseurs will enjoy exploring the 19th-century pottery collection at the Charles Hosmer Morse Museum of American Art. The impressive collection features the largest body of work by Louis Comfort Tiffany.
Also, you can’t miss out on the Casa Feliz Historic Home Museum, an Andalusian-style farmhouse depicting the architectural and cultural influences in the Winter Park community. For a more immersive experience, shop at the Winter Park Farmers Market. Finally, for lodging, consider the luxurious Alfond Inn at Rollins for a regal sleep.
Lake Placid
One of the most scenic towns in Florida, Lake Placid is often confused with its namesake in New York, which hosted the 1932 and 1980 Winter Olympic Games. While the town has its own storied past, visitors can learn more at the Lake Placid Historical Society, which houses a collection of local archives, artifacts, and memorabilia. Lake Placid's location near several bodies of water ensures a variety of aquatic adventures for tourists. At Lake Placid and Mirror Lake, guests can choose from activities like swimming, jet skiing, motor boating, kayaking, and paddleboarding to make the most of water-based fun.
Lake Placid has a fair share of quirky museums to check out. The American Clown Museum & School is a notable example, documenting the history of clowning through diverse clown memorabilia. For accommodation, consider the Lakeshore Resort Motel, which offers a relaxing atmosphere and fantastic sunset views.
DeLand
As the home of Stetson University, DeLand boasts an upbeat vibe enriched by a vibrant art and culture scene. The youthful college population injects a lively energy into this quaint Volusia County community. There is a broad spectrum of experiences in DeLand, including touring Stetson Mansion. Built in 1886, this iconic landmark stands as the state's first luxury estate. Several art centers ensure connoisseurs have something to look forward to. At Athens Theater, they can catch a moving live performance featuring plays and concerts, while the Museum of Art-DeLand invites them to browse a lovely fine art collection.
For outdoor enthusiasts, Hontoon Island State Park offers endless opportunities. This 1,648-acre nature space offers a variety of recreational activities, including fishing, hiking, kayaking, biking, canoeing, and camping. While there is no shortage of B&Bs in DeLand, Comfort Inn & Suites is an excellent choice for accommodation.
Venice
Venice, with its fourteen miles of picturesque sandy shorelines, is a dream destination for beachgoers. It offers abundant family-friendly water-based adventures and charming shopping opportunities in an easygoing environment. There are many beaches to check out, but Venice Beach is one of the most popular. It has a scenic pier where visitors can stroll for views of dolphins and different shorebird species. One of the best experiences in the town lies in Historic Downtown Venice. Exploring the peaceful streets reveals an eclectic assortment of shops, boutiques, restaurants, art galleries, and parks.
For history buffs, the 1927 Historic Venice Train Depot is an enticing stop. Inside, exhibits document the town's railroad history, dating back to its establishment. And when it's time to call it a day, the Inn at the Beach offers a laid-back environment for a good night's sleep.
Destin
This popular Panhandle destination embodies the sheer beauty of Florida’s Emerald Coast. Famous for its pristine Gulf of Mexico beaches, it beckons tourists for a weekend of fun and relaxation. You can explore the idyllic beach scenery inside Henderson Beach State Park by strolling on silky-smooth sand and enjoying sparkling water views. Also, soak in some of the best vistas along the Destin Harbor Boardwalk while stopping at the various restaurants, shops, pubs, and souvenir stores lining the lively corridor.
Those interested in Destin's past can uncover its fishing heritage at the Destin History & Fishing Museum. The museum takes visitors on a journey from the early 1800s pioneer days to modern Destin, chronicling the town's fishing and industrial history. Also, shopaholics yearning for retail therapy will find marvelous shopping opportunities at Destin Commons. But before all that, remember to check into Destin Inn & Suites for your nightly stays.
Key West
The southernmost point in Florida is a tropical paradise that allows vacationers to revel in a dreamy coastal atmosphere with gorgeous beaches and magical sunsets. Key West has its fair share of historical gems to explore, starting with Fort Zachary Taylor Historic State Park. Designated a National Historic Landmark, the fort dates back to the Civil War era and exhibits artifacts related to the United States military. The park also includes the Truman Little White House, an 1890 mansion that served as President Truman’s residence for 175 days.
Numerous local outfitters offer boating excursions, providing a unique perspective of the town from the water. One notable option is the Yankee Freedom Dry Tortugas Ferry, offering an unforgettable trip. Nature enthusiasts will enjoy visiting the Key West Butterfly and Nature Conservatory. For accommodation, NYAH Key West offers quality lodging without breaking the bank.
Anna Maria Island
Anna Maria Island, a charming resort town nestled between Florida's mainland and the azure waters of the Gulf of Mexico, is known for its powdery white beaches with breathtaking coastal vistas. Tourists are naturally drawn to the family-friendly Manatee Public Beach. Amenities such as restrooms, bike racks, picnic areas, and a playground make it one of the area's top spots for beachgoers. For over a century, the historic Anna Maria City Pier has been a scenic gateway to the waterfront, welcoming sightseers since 1911. Picturesque rows of businesses line the length of the pier, ranging from shops and bars to seafood restaurants like the City Pier Grill and Bait.
No visit to the island is complete without exploring its aquatic surroundings. Among the top excursions is the Anna Maria Island Dolphin Tours, unveiling an opportunity to spot dolphins and other marine wildlife in their natural habitat from the deck of a tour boat. Given its paradisiacal scenery and exquisite water recreational activities, the Anna Maria Beach Resort is among the best places to stay in the area.
Wrapping Up
While famous cities like Miami and other popular destinations in Florida receive the bulk of the state's tourists, the thick crowds and excessive commotion can prove too much for those after a relaxed retreat. Luckily, these small towns in Florida deliver the perfect alternative without taking away from the experience. With their beautiful natural scenery, captivating history, rich culture, and endless water adventures, these towns showcase a fresh side of the Sunshine State that not many get to experience. For those looking to escape the crowds and enjoy an easygoing rural weekend getaway, these towns offer an ideal experience.
