While Florida boasts an array of world-famous theme park attractions, it is also home to an array of small-town charms that are perfect for a weekend of escaping the hustle and bustle of everyday life. Kick back and relax and experience the quaint charm and slower pace of life that these small towns offer, where you can soak up the sunshine, explore the city’s rich history and shop for antique treasures. Immerse yourself in the friendly atmosphere and reconnect with nature at one of Florida’s coolest small cities that are perfect for a weekend getaway in fall.


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DeFuniak Springs DeFuniak Springs
Credit: Ebyabe
DeFuniak Springs

DeFuniak Springs (Nearby Hotels)

Boasting an array of beautiful Victorian homes, admiring the architecture in the downtown historic district of DeFuniak Springs is a pleasant way to spend an afternoon. Built around Lake DeFuniak, you can take advantage of the excellent fishing lakes in the surrounding area or go shopping for antique treasures in the small boutique shops. Spend a night in one of the charming bed and breakfast accommodations and pop into one the local restaurants for a delectable meal of fresh seafood.

Matlacha Matlacha
Credit: Don Johnson 395

Matlacha (Nearby Hotels)

A small town with a big personality, Matlacha is a friendly rural fishing village, delighting visitors with its burst of vibrant colored displays, as it is home to free-spirited artists who have set up small shops where you can purchase one-of-a-kind souvenirs. Admire the lush landscapes and local artwork at Lovegrove Gallery & Gardens before browsing exhibits that showcase the area’s history at MOTI – The Museum of Islands or spending a day outside at Pine Island.

St. George Island St. George Island State Park
Credit: Arturo Donate
St. George Island State Park

St. George Island (Nearby Hotels)

A quiet area with 28 miles of undeveloped beaches, St. George Island offers unspoiled beauty that can be appreciated throughout the year. Explore the area on two wheels at the 17 miles of paved bike paths, admire the array of migrating birdlife, or get out on the water for a canoeing or kayaking adventure. Take a guided boat tour to spot the pods of dolphins or take a sunset cruise to appreciate one of the last preserved barrier islands in Florida.

Cedar Key Cedar Key
Credit: Monik Markus
Cedar Key

Cedar Key (Nearby Hotels)

Giving visitors a glimpse of what Florida was like many decades ago, Cedar Key exemplifies an Old Florida ambiance. Located on the Nature Coast, its rustic atmosphere and slower pace of life are perfect for those who want to get away from it all. You’ll find lovely beach areas, plenty of fishing opportunities and natural preserves that are best enjoyed after a hearty bowl of clam chowder at one of the local seafood establishments.

Micanopy Micanopy, Florida
Micanopy, Florida

Micanopy (Nearby Hotels)

Nicknamed “The Little Town That Time Forgot”, Micanopy is a historic area with rustic shops and welcoming locals. The oldest inland town in Florida, this tiny jewel of Alachua County is the perfect place to spend a weekend antique shopping and exploring its untouched natural landscapes. Head out to nearby Paynes Prairie Preserve State Park to see wild bison and horses roaming its lands from a 50-foot observation tower, or go hiking, biking and horseback riding.

Fernandina Beach Fernandina Beach
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Fernandina Beach

Fernandina Beach (Nearby Hotels)

Located on Amelia Island, Fernandina Beach is a quaint area that has been a local favorite for multiple generations. Meander through the city’s downtown area to discover boutique shops and quaint restaurants, while history buffs will want to visit Fort Clinch State Park to see the Civil War-era fortress or the Amelia Island Museum of History to learn about the island’s past. Spend an afternoon golfing, horseback riding on the beach or spotting wildlife on a kayaking tour.

Gulfport Gulfport

Gulfport (Nearby Hotels)

A small town with an array of family-friendly attractions, Gulfport is home to an artsy community with a colorful personality. With a slogan like “Keep Gulfport Weird” its hard to not love this city, as its small independent shops, easy-going waterfront restaurants and beautiful beach area make it a popular destination throughout the year. Head out to Clam Bayou Nature Preserve when you’re in need of a dose of nature, explore the thriving arts scene, or simply watch a sunset from Williams Pier.

Steinhatchee Steinhatchee
Credit: Rain0975

Steinhatchee (Nearby Hotels)

Considered the gateway to Florida’s Nature Coast, Steinhatchee is a charming fishing town in the Big Bend region. A combination of quiet landscapes and Victorian homes, you’ll be immediately lured in by its towering live oaks covered with Spanish moss and scenic stretch of white sand beaches. You’ll find diverse wildlife and abundant fishing opportunities to keep you busy, while exploring the area on a bike, pontoon boat or sunset cruise is also a pleasure.

Apalachicola Apalachicola
Credit: patchattack

Apalachicola (Nearby Hotels)

A friendly fishing town, Apalachicola is one of Florida’s hidden gems. Rustic charm at its best, this area is known for its friendly locals and world-renown seafood. With over 900 historic listings that include small cottages and stained glass churches, you’ll be hard-pressed to find any traffic or noise in this laid-back slice of paradise. To explore its most beautiful landscapes, hit the trails in Apalachicola National Forest or Tate’s Hell State Forest for the day.

Mount Dora Mount Dora
Credit: facebok.com
Mount Dora

Mount Dora (Nearby Hotels)

One of the most popular small towns in Florida, Mount Dora is beloved for its 19th-century clapboard houses, antique shops and outdoor cafes that line its historic district. Offering the best of both worlds, you can go shopping for valuable collectibles at Renninger’s Antique Center & Farmer’s Flea Market before soaking up the scenic natural setting around Lake Dora. Go on a fishing excursion, sample local cuisine in the gourmet restaurants or relax with a glass of vino at The Cellar Door winery.

Santa Rosa Beach Grayton Beach State Park, Santa Rosa Beach
Credit: goldenticket76
Grayton Beach State Park, Santa Rosa Beach

Santa Rosa Beach (Nearby Hotels)

You’re spoiled for choice with outdoor adventures in Santa Rosa Beach, a luxurious beach town on Florida’s Emerald Coast. In addition to its miles of clear blue waters, you have easy access to some of Florida’s most picturesque state parks. You can go paddling in Grayton State Beach Park, hike the trails in Camp Helen State Park, or relax with a day of fishing on the lake in Topsail Hill Preserve State Park and admiring the colorful displays in Eden Gardens State Park.

Anna Maria Island Anna Maria Island
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Anna Maria Island

Anna Maria Island (Nearby Hotels)

A perfect weekend escape to enjoy laid-back vibes and picturesque natural scenery, life on Anna Maria Island is easy-going. Avoid the crowds and enjoy a vacation of solitude, where the biggest buzz is watching the cyclists cruise the area and soaking up the turquoise water views. Dine on local delicacies at Gulf view restaurants, visit an art gallery or get out on the water on a kayak or paddleboarding excursion.