25 charming small towns in Florida worth a weekend road trip

Dunedin

District to explore: Main Street
Main Street is the cosmopolitan shopping and dining roadway in Dunedin, host to a miscellany of interesting storefronts. Visitors can stop for a drink at Dunedin Brewery, the oldest microbrewery in Florida; or purchase mystical oddities or curios at Enchanted Earth, the official witch shoppe of Dunedin; or get a sweet at Strachan’s Ice Cream and Desserts, which is renowned for the award-winning carrot cake and homemade waffle cones.

Photo via City of Dunedin/Facebook

Mount Dora

District to explore: Donnelly Street
A trip to Donnelly Street can provide the best of something old and something new. Donnelly boasts an impressive antiquing scene. Snag some treasures from the past and afterwards stop by celebrity chef Norman Van Aken's restaurant, 1921, for some modern Florida cuisine only a street away.

Photo via City of Mount Dora/Facebook

Micanopy

District to explore: Cholokka Boulevard
Head to “the town that time forgot” for a day of seeing unique historical buildings that have been repurposed for small shops and businesses. Micanopy has many shops to amuse the antique-lover, along with stores that sell arts, crafts, and home furnishings. The town is filled with massive oaks covered in Spanish moss, and author Marjorie Kinnan Rawlings' home is nearby -- tours are available. While there isn’t a huge selection of restaurants, there are a few cafes to grab a bite to eat, such as Old Florida Cafe.

Photo via Old World Cafe/Facebook

Siesta Key

District to explore: Ocean Boulevard
Siesta Key Village is an island about 20 minutes from the mainland of Sarasota, with four distinct beaches. The main street is Ocean Boulevard, which is located towards the north end of the island. Beach Bazaar of Sarasota will take care of all your vacation and beach shopping needs, as well as any souvenir searching you might want to do. For food, there’s the well-known Siesta Key Oyster Bar (SKOB to locals), which serves seafood and frozen alcoholic drinks and provides open-air dining and live entertainment.

Photo via Adobe Images

Winter Garden

District to explore: Plant Street
Plant Street Market is open seven days a week, and has 20 food vendors that offer a taste of locally produced or craft-made meals and treats. At the same location, you can also buy clothing and crafts. You can visit Crooked Can Brewing, a local brewery which is also a hotspot for artisan food vendors to set up shop. For a change of pace in entertainment, catch a play or concert at Garden Theatre.

Photo via Plant Street Market/Facebook

Tarpon Springs

District to explore: Dodecanese Boulevard
One would be hard-pressed to find a more romantic destination than Tarpon Springs, located where a series of bayous meets the Gulf. Dodecanese Boulevard the town’s main street, historically, was the town’s major artery for the town’s sponge industry. Now, visitors can stroll down the boulevard to visit museums dedicated to the town’s industrial history, shop at the boutiques and storefronts and after soaking (pun intended) up the city cap it off with a glass of wine at Wine on the Docks.

Photo via City of Tarpon Springs/Facebook

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 Adobe Images

Apopka

District to explore: Main Street
Apopka is the second-largest city in Orange County after Orlando. Known mainly for its proximity to many of the natural spring parks, Apopka also has a museum, a winery, and horseback riding tours. The town also has many hole-in-the-wall restaurants and some small stores with souvenirs. One of those restaurants is Porkie’s Original Barbecue, which promises savory meats after a day of exploring the town.

Photo via Porkie's Original BBQ/Facebook

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 Adobe Images

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 Adobe Images

Cedar Key

District to explore: D Street
D Street is the three-block-long main street of the second-oldest town in Florida, Cedar Key. The buck doesn’t stop there, while Cedar Key is quintessential “Old Florida,” where you are more likely to find a “gone fishing” sign in a store window than a McDonald's or a Walmart, the town’s main street is awash with life and flavor from the colorful murals to the fresh clams, which are touted by locals as being some of the sweetest in the world.

Photo via Adobe Images

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 Downtown Chipley/Facebook

Stuart

District to explore: Osceola Street
Stuart has a lot to offer, starting with its free open-air concerts on the Riverwalk stage every Sunday. You can walk along the St. Lucie River and then enjoy Osceola Street, where you will find April Daze Boutique, which sells home decor, wines, and women’s clothing and accessories. Next, head over to the jazzy atmosphere of Osceola Street Cafe, located in the heart of downtown and serving up fresh, locally sourced fish, meats, and veggies.

Photo via City of Stuart/Facebook

Venice

District to explore: Venice Avenue
Originally modeled to resemble Venice, Italy, Venice Avenue is as much a treat for the architectural enthusiast as it is the avid shopper. In addition to boutiques, restaurants, and assorted other stores, Venice Ave. is home to the nation’s largest community theater.

Photo via Adobe Images

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 City of DeLand/Facebook

Sanford

District to explore: East First Street
Located just under 40 minutes from Orlando, Sanford is a charming historic town with some fun monthly events. Alive After 5 is a block party with live music, local artists, and of course, food and beer. It happens every second Thursday along the main street. There’s also the Sanford Artwalk on every third Saturday, where you can see local artists vie for Best in Show and People’s Choice. Make sure to check out Hollerbach’s Willow Tree Cafe, a well-loved restaurant serving up classic German dishes and providing live music.

Photo via City of Sanford/Facebook

Delray Beach

District to explore: Atlantic Avenue
Atlantic Avenue is a happening place in Delray beach on a Friday night. An affluent area, Atlantic Avenue is host to a number of upscale restaurants and boutiques.

Photo via Adobe Images

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 Adobe Images

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 Adobe Images

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 Adobe Images