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12 Best Cities in Florida for a Fall Weekend Getaway

While Florida boasts an array of world-famous theme park attractions, it is also home to a variety of charming small towns 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 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 most incredible small cities that are perfect for a weekend getaway in the fall.

Fernandina Beach Fernandina Beach
Credit: Fernandina Beach by bigstock.com

Fernandina Beach

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. At the same time, 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, and then wind down at a charming bed and breakfast.

Matlacha Matlacha


Matlacha is a friendly rural fishing village, a small town with a big personality, delighting visitors with its burst of vibrant colored displays. 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 nearby MOTI – The Museum of Islands or spending a day outside Pine Island.

Santa Rosa Beach Aerial View of Breaking Waves at Santa Rosa Beach Florida
Credit: Aerial View of Breaking Waves at Santa Rosa Beach Florida by © William Gibson | Dreamstime.com

Santa Rosa Beach

You’re spoiled for choice with outdoor adventures in Santa Rosa Beach, a luxurious beach town on Florida’s Emerald Coast and one of America’s favorite towns. 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.

Mount Dora Mount Dora

Mount Dora

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. There are plenty of accommodation options nearby, from historic inns to bed and breakfasts.

Anna Maria Island Anna Maria Island, Florida
Credit: Anna Maria Island, Florida by © Mark Winfrey | Dreamstime.com

Anna Maria Island

Life on Anna Maria Island is easy-going – the perfect weekend getaway to enjoy laid-back vibes and picturesque natural scenery. Avoid the crowds and enjoy a vacation of solitude, where the biggest buzz is watching the cyclists cruise the area and soak up the turquoise water views from your beachfront vacation rental. Dine on local delicacies at gulfview restaurants, visit an art gallery, or get out on the water on a kayak or paddleboarding excursion.

Micanopy Micanopy
Credit: Micanopy by © Hblamb | Dreamstime.com


Nicknamed “The 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 of antique shopping and exploring its untouched natural landscapes. Head 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.

St. George Island St. George Island
Credit: St. George Island by Flickr

St. George Island

A quiet area with 28 miles of undeveloped beaches, St. George Island offers unspoiled beauty you can appreciate 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 Florida’s last preserved barrier islands.

Gulfport Gulfport


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,” it’s hard not to 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 need a dose of nature, explore the thriving arts scene, or watch a sunset from Williams Pier.

Navarre Navarre Beach, Florida
Credit: Navarre Beach, Florida by © Michael Wood | Dreamstime.com


Home to one of the most beautiful beaches in Florida’s Panhandle, Navarre is a small coastal town full of exciting activities in the fall. The temperature typically hits the 70s throughout October and November, and it is a perfect time to stroll the beach or go fishing on the Navarre Beach Fishing Pier. A short drive will take you to the scenic hiking trails in Blackwater River State Forest in Historic Milton. Take advantage of the blue skies and crisp air by attending one of the town’s most popular annual fall events, including a Halloween-themed month of October at the Navarre Beach Sea Turtle Conservation Center and a trick-or-treating trail at Gulf Breeze Zoo.

Steinhatchee Steinhatchee Falls
Credit: Steinhatchee Falls by Rain0975


Steinhatchee is a charming fishing town in the Big Bend region, considered the gateway to Florida’s Nature Coast. 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.

DeFuniak Springs Chipley Park at Lake DeFuniak, Defuniak Springs
Credit: Chipley Park at Lake DeFuniak, Defuniak Springs by defuniaksprings.net

DeFuniak Springs

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 of the local restaurants for a delectably fresh seafood meal.

Apalachicola Apalachicola
Credit: Apalachicola by © Cateandstock/dreamstime.com


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.

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