Strewn throughout the Sunshine State, these best fall destination towns promise clear days and warm temperatures where you can still hit the beaches in Venice and enjoy outdoor parks in Winter Park. From Mount Dora's two great lakes with the best bass fishing to swimming with the manatees in the Crystal River, there's even an alligator farm in St. Augustine!
Blending culture flawlessly into the fall-time nature under the warm Floridian sunshine, you can enjoy cozy outdoor pursuits and experiences in between the state's staple seafood and shopping scenes. Realize all your fall getaway dreams with this list, from ghost tours in time for Halloween to inspiring an international getaway in Tarpon Springs, a Greek coastal town, or Venice, a beautiful Italian city dressed in pink.
Crystal River

Beloved by the sun as much as nature-loving tourists and their kids, you can observe these comic creatures on a memorable family getaway from the dreary falltime city. The charming downtown area, replete with small-town businesses, welcomes you warmly to peruse and cozy up in the family-friendly atmosphere in between swimming along these gentle giants in the springs, as one of the only places in the country with such a unique nature interaction. The Plantation on Crystal River, with stately white buildings and real Southern charm, promises a fun day exploring on a stroll, with water pursuits, golf, and fine dining against a glorious sunset over the river.
7 Most Picturesque Small Towns In Florida's Nature CoastThere is a reason that Florida's Nature Coast has its name, featuring many picturesque coastal towns that offer major natural exploration opportunities.
Dunnellon

While other states brace for the cold winds and early snow, you can spend days outdoors, with warm weather here lasting through the fall. From river strolls and picnics to immersive nature hikes through Rainbow Springs State Park with its beautiful trails, you can also go paddling, tubing, and swimming within a painting-like scenery of an autumnal color palette. Afterward, the highest-rated tourist and local favorite, Swampy's Bar & Grille, perched over the river, offers a cozy outdoor setting under blue umbrellas with water views from above.
Gulfport

With easy access just west of St. Petersburg and Treasure Island Beach Resort, the town in the shadow of the popular Tampa/Clearwater area stays crowd less for an intimate getaway with your loved ones. You can enjoy browsing through the colorful lineup of boutiques along Beach and Shore Boulevards, the heart of the historic downtown with views of Boca Ciega Bay. Void of parking meters and chain stores, but just the perky locals who call their home a "small town with a big heart," Gulfport was also the "best food town" in the United States. The eclectic dozen eateries do Rand McNally's claim justice, including the vegetarian deli at Golden Dinosaurs and Mediterranean cuisine at Neptune Grill.
Matlacha

You can start along the main stretch at The Perfect Cup before spending an afternoon at the big Matlacha community park with cycling and walking paths. With streets full of art and a quirky spirit along the craft stands and colorful mobile homes, there are plentiful local shops to peruse for gifts and fresh seafood markets with more bohemian vibes. Discover the island's unique and eccentric homes on a walk through the streets along the "comb" bristles, and then back to the notable Blue Dog Bar & Grill for dinner and a sunset view from the shores before hitting the local bar scene.
8 Adorable Small Towns In FloridaFrom coastal gems to inland cities preserved in time, each small town offers its own unique beauty that can only be found when exploring every nook and cranny.
Micanopy

The charming oak-lined Cholokka Boulevard, verdant through the fall, is a joyous sight on a vintage shopping spree through the hot lineup of boutiques and the annual Fall Harvest Festival, which unravels in art and music right here. Abundant in more than just antiques, there are happening cafes and thriving art galleries to visit, from Delectable Collectables to the Micanopy Historical Society Museum. You can recharge at the aptly named Old Florida Cafe or hit the popular, highly rated Pearl Country Store & Barbecue along Hwy 441 for dinner.
Mount Dora

You can experience all the pleasures of the bucolic Old Florida lifestyle amid quiet bed and breakfasts, country inns, and a lineup of tasty dining options, including outdoor cafes, gourmet restaurants, and wineries. From its 100-year-old historic village to an annual event unraveling along the waterfront or an antiquing day in the city center, there's something for everyone in Mount Dora. For a cozy fall day, stop at the old railroad station under timeless charm while browsing through the trendy valuables, antiques, and collectibles downtown.
7 Most Charming End-Of-Road Towns In FloridaA true smorgasbord of curiosity, each stop represents a different aspect of Florida’s unique personality.
St. Augustine

St. Augustine is a walkable town with narrow streets lined by countless cultural gems like museums and historic landmarks, including the iconic Castillo de San Marcos. Having changed hands many times between Spain and Britain, European sights prevail in famous forts, the Colonial Quarter, and Greek influence. From Ponce de Leon's "Fountain of Youth" to the Oldest Wooden Schoolhouse, you can spend days discovering rich history before diving into 21st-century attractions like paranormal ghost tours downtown in time for Halloween or a professional golf course. There's also shopping along the cobblestoned historic St. George Street to the upscale Ponte Vedra Beach and farmers' markets before fine dining on the day's fresh catch with water views.
Tarpon Springs

You can revel in their most potent gift of Greek food offerings, particularly along the Dodecanese Boulevard, like the highest-rated Mykonos or Dimitri's on the Water. Downtown Tarpon Springs, on the National Register of Historic Places, is a charming blend of old and new, Greek and Americana, with art galleries, antique stores, and specialty shops within 1800s buildings. The renowned Tarpon Springs Performing Arts and Cultural Center promises many falltime evenings getting acculturated over a theater performance, a concert, and other quality programs amid more art and historical exhibits.
Venice

While you sift through the sands for the abundant fossilized shark's teeth to take home as a unique keepsake or souvenir for a friend, golf lovers can enjoy their favorite pastime with excellent courses in the greater Venice area. As the Main Street City in the Sunshine State, Venice's downtown is a graceful centerfare, originally planned in 1925, comprising fine Italian architecture and beautifully landscaped boulevards—a joy to the eye. Enjoy the atmosphere akin to a real Italian city along Venice Avenue with pink Italian Renaissance buildings and the best-unobscured views to capture it all without crowds during the fall.
Winter Park

More than just a suburb, Winter Park is an arts and culture destination in its own right, with a small-town feel near the Disney scene that feels guarded against all the Mickey ears and replete with cultural institutions for cozy fall-day wanderings. The highly rated Rollins College, Florida's first four-year university to visit, owns the Charles Hosmer Morse Museum of Natural Art—both worthy visits. When you stay at one of The Alfond Inn's 112 tremendous guest rooms, what you pay directly benefits the scholarship program at Rollins, while you get a full range of amenities, a pool, and a riveting art collection to view.
Just imagine Florida's already glorious nature getting its gems dressed up for the fall season of pumpkins and giving thanks. You don't have to imagine or worry about being too late, but start packing your bags for these destination towns, which readily welcome fall enthusiasts after the heavy summer stampede with great places at fair prices.
These ten historic towns are year-round destination getaways from the city, including the oldest European settlement in the US, St. Augustine. With many towns along the Nature Coast, like Crystal River and Dunnellon, you will be steps away from the downtown to quintessential experiences like swimming with manatees that escape the colder Gulf of Mexico waters to Crystal River.