25 small Florida towns you should be exploring this weekend

One of the great things about living in Florida is that no matter which way you drive, you'll probably cruise through a charming tiny town filled with cool shops and unique hole-in-the-wall restaurants. Time to gas up the car. Here are a few of our favorite small towns that are always worth the trip.

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DeLand
District to explore: Woodland Boulevard
DeLand has many cultural attractions along its main street, along with local boutiques and small spots to grab coffee or a snack. DeLand’s must-visit shopping center is South of New York market, where you can check out antique and vintage furniture, gifts and clothing while you drink from the selection of international and local beer and wine. BakeChop on Artisan Alley is a great dining option with seasonal dishes and locally sourced ingredients.
Photo via Kolter Homes/Youtube

DeLand

District to explore: Woodland Boulevard
DeLand has many cultural attractions along its main street, along with local boutiques and small spots to grab coffee or a snack. DeLand’s must-visit shopping center is South of New York market, where you can check out antique and vintage furniture, gifts and clothing while you drink from the selection of international and local beer and wine. BakeChop on Artisan Alley is a great dining option with seasonal dishes and locally sourced ingredients.

Photo via Kolter Homes/Youtube
Ormond Beach
District to explore: Granada Boulevard
Granada Boulevard is the hub of Ormond Beach and traverses the Halifax River. Walking along the boulevard, you can find Ormond Beach’s local boutiques, along with ice cream and coffee shops, and City Hall, which hosts a monthly farmers market. During the day, you can explore the Granada Plaza Shopping Center. The 31 Supper Club Steakhouse offers craft cocktails and live jazz music, with a unique fine dining atmosphere reminiscent of a Vegas club. 
Photo via kristinheron/Instagram

Ormond Beach

District to explore: Granada Boulevard
Granada Boulevard is the hub of Ormond Beach and traverses the Halifax River. Walking along the boulevard, you can find Ormond Beach’s local boutiques, along with ice cream and coffee shops, and City Hall, which hosts a monthly farmers market. During the day, you can explore the Granada Plaza Shopping Center. The 31 Supper Club Steakhouse offers craft cocktails and live jazz music, with a unique fine dining atmosphere reminiscent of a Vegas club.

Photo via kristinheron/Instagram
Boca Grande
District to explore: Park Avenue
Boca Grande has long attracted the wealthier set as a natural seaside haven, but its Old Florida charm is for everyone to enjoy. After walking along the three blocks of downtown, you can explore the well-preserved historical sites of the Gasparilla Inn and the 1890 Boca Grande Lighthouse. If you’re in the need for any supplies before hitting the beach or just want some Boca Grande spirit to take with you, hit up Holly’s Island Shop. If you want to visit a local eatery, stop by PJ’s SeaGrille and enjoy their artistically presented seafood meals and enjoy the homey, timber house building which includes patio seating.  
Photo via Rich Taylor/ Youtube

Boca Grande

District to explore: Park Avenue
Boca Grande has long attracted the wealthier set as a natural seaside haven, but its Old Florida charm is for everyone to enjoy. After walking along the three blocks of downtown, you can explore the well-preserved historical sites of the Gasparilla Inn and the 1890 Boca Grande Lighthouse. If you’re in the need for any supplies before hitting the beach or just want some Boca Grande spirit to take with you, hit up Holly’s Island Shop. If you want to visit a local eatery, stop by PJ’s SeaGrille and enjoy their artistically presented seafood meals and enjoy the homey, timber house building which includes patio seating.

Photo via Rich Taylor/ Youtube
Destin
District to explore: Destin Harbor Boardwalk
Known as the “World’s Luckiest Fishing Village,” Destin’s main street is the Destin Harbor Boardwalk. The fisherman's spirit really is the soul of this small Florida town, which is home to the second largest fishing fleet in Florida. Walking along the boardwalk, you’ll find places to eat, drink, enjoy local entertainment, and rent equipment to head out on the water. Destin Commons is the place to shop, check out local art, and bowl. For your meal, check out proud local restaurant AJ’s Seafood & Oyster Bar, where you can watch the charter boats come in with their daily catch and get prime seafood. 
Photo via destinboardwalk/Instagram

Destin

District to explore: Destin Harbor Boardwalk
Known as the “World’s Luckiest Fishing Village,” Destin’s main street is the Destin Harbor Boardwalk. The fisherman's spirit really is the soul of this small Florida town, which is home to the second largest fishing fleet in Florida. Walking along the boardwalk, you’ll find places to eat, drink, enjoy local entertainment, and rent equipment to head out on the water. Destin Commons is the place to shop, check out local art, and bowl. For your meal, check out proud local restaurant AJ’s Seafood & Oyster Bar, where you can watch the charter boats come in with their daily catch and get prime seafood.

Photo via destinboardwalk/Instagram
Apalachicola
District to explore: Market Street
Apalachicola’s Market Street has many charming local shops, like the Apalachicola Chocolate Company. Grady Market offers the biggest collection of clothing and accessories and is located in the building that once housed the French consulate. When it comes time to choose where to get a bite to eat, you won’t be lacking in choices -- you may want to try Hole in the Wall, which specializes in Apalachicola oysters and seafood classics. 
Photo via ali.grof/Instagram

Apalachicola

District to explore: Market Street
Apalachicola’s Market Street has many charming local shops, like the Apalachicola Chocolate Company. Grady Market offers the biggest collection of clothing and accessories and is located in the building that once housed the French consulate. When it comes time to choose where to get a bite to eat, you won’t be lacking in choices -- you may want to try Hole in the Wall, which specializes in Apalachicola oysters and seafood classics.

Photo via ali.grof/Instagram
Fernandina
District to explore: Centre Street
A stroll along Centre Street will bring you to all sorts of eclectic shops, including Celtic Charm, Blue Door Artists, and Pelindaba handcrafted lavender products. You can take a horse-drawn carriage ride and learn about the history of the Old Florida houses. For some nice outdoor dining in charming quarters, head to Leddy’s Porch Bistro at the Florida House Inn, serving up Southern comfort food with vegetarian and gluten-free options. 
Photo via Birkenwald47/Youtube

Fernandina

District to explore: Centre Street
A stroll along Centre Street will bring you to all sorts of eclectic shops, including Celtic Charm, Blue Door Artists, and Pelindaba handcrafted lavender products. You can take a horse-drawn carriage ride and learn about the history of the Old Florida houses. For some nice outdoor dining in charming quarters, head to Leddy’s Porch Bistro at the Florida House Inn, serving up Southern comfort food with vegetarian and gluten-free options.

Photo via Birkenwald47/Youtube
Flagler Beach
District to explore: Central Avenue
Flagler Beach is famous for its six miles of uninterrupted beaches. After exploring the beach and the nearby parks, visit the shops that sell locally made clothes and pottery. Frankie Alice’s Beachside Boutique sells high-quality and unique clothes and accessories.The farmers market is every Friday and Saturday, and there you can find locally produced food, clothing, crafts, and more. After exploring, you can try some award-winning wines made at the Flagler Beachfront winery.
Photo via OfficeDivvy/Youtube

Flagler Beach

District to explore: Central Avenue
Flagler Beach is famous for its six miles of uninterrupted beaches. After exploring the beach and the nearby parks, visit the shops that sell locally made clothes and pottery. Frankie Alice’s Beachside Boutique sells high-quality and unique clothes and accessories.The farmers market is every Friday and Saturday, and there you can find locally produced food, clothing, crafts, and more. After exploring, you can try some award-winning wines made at the Flagler Beachfront winery.

Photo via OfficeDivvy/Youtube
Captiva Island
District to explore: Captiva Drive
Captiva Drive starts at Turner Beach, winding past tropical flora and ending at downtown Captiva. Captiva is a prime location to enjoy the beach and water sports, along with appreciating the nature. When you head back to the shops, Chadwick’s Square South is good for strolling and browsing the various stores. For a unique dining experience, head to the Bubble Room, for a wide selection of deliciously prepared meats and salads in an eclectic setting. 
Photo via emilyswarner/Instagram

Captiva Island

District to explore: Captiva Drive
Captiva Drive starts at Turner Beach, winding past tropical flora and ending at downtown Captiva. Captiva is a prime location to enjoy the beach and water sports, along with appreciating the nature. When you head back to the shops, Chadwick’s Square South is good for strolling and browsing the various stores. For a unique dining experience, head to the Bubble Room, for a wide selection of deliciously prepared meats and salads in an eclectic setting.

Photo via emilyswarner/Instagram
New Smyrna Beach
District to explore: Flagler Avenue and Canal Street
New Smyrna Beach maintains its small-town charm in all the local offerings along its two main streets. If you’re in the mood to browse, the New Smyrna Beach Antique Mall offers a collection of jewelry, art and lightly used furniture. Small shops like Lola’s Boutique promise clothing and accessories you won't find anywhere else. After shopping, you can head for a bite to eat at Atlantis Bistro, a cozy Italian restaurant located on Flagler Avenue known for the incredible lasagna served on the weekends. 
Photo via shellebel/Instagram

New Smyrna Beach

District to explore: Flagler Avenue and Canal Street
New Smyrna Beach maintains its small-town charm in all the local offerings along its two main streets. If you’re in the mood to browse, the New Smyrna Beach Antique Mall offers a collection of jewelry, art and lightly used furniture. Small shops like Lola’s Boutique promise clothing and accessories you won't find anywhere else. After shopping, you can head for a bite to eat at Atlantis Bistro, a cozy Italian restaurant located on Flagler Avenue known for the incredible lasagna served on the weekends.

Photo via shellebel/Instagram
Chipley
District to explore: Highway 77
Chipley is home to the beautiful Falling Waters State Park. After a day of exploring the nature trails, you can head to the downtown district to explore Emmie & Co., a one-of-a-kind gifts and custom embroidery store. Stop off at Javier’s Mexican Grill, where you’ll be able to get some authentic Mexican food right in downtown and see what local cause the restaurant is supporting.  
Photo via Main Street Market/Facebook

Chipley

District to explore: Highway 77
Chipley is home to the beautiful Falling Waters State Park. After a day of exploring the nature trails, you can head to the downtown district to explore Emmie & Co., a one-of-a-kind gifts and custom embroidery store. Stop off at Javier’s Mexican Grill, where you’ll be able to get some authentic Mexican food right in downtown and see what local cause the restaurant is supporting.

Photo via Main Street Market/Facebook