15 charming Florida towns worth a weekend road trip from Orlando

Sanford

30 minutes from Orlando
Nestled along the southern shores of Lake Monroe, Sanford is about 40 minutes due north of Orlando on I-4. The former hub of Central Florida is coming back into its own with annual festivals, such as Sanford Porchfest and Love Your Shorts Film Festival, providing plenty of reasons to plan a visit. Grab savory schnitzel and beers by the boot at Hollerbach's Willow Tree Cafe or some booze-infused handmade marshmallows from Wondermade.

New Smyrna Beach

1 hour and 6 minutes to Orlando
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.

Venice

3 hours and 25 minutes to Orlando
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. Venice Beach is also known for its shark teeth and seashells galore along its Atlantic sands. If you’re looking for even bigger shark teeth, though, grab a mask and go snorkeling in Caspersen Beach.

DeLand

48 minutes from Orlando
Once known as Persimmon Hollow for the wild persimmons that grew there in abundance, DeLand is located about an hour north of Orlando on I-4. From Stetson University to the DeLand Mansion, the town is ripe with history — and provides the perfect jumping-off point for outdoor excursions. Take in a show at the historic Athens Theatre, plunge into the waters at Ponce de León Springs State Park or grab an authentic Cuban coffee at Chicas Cuban Cafe.

Mount Dora

40 minutes to Orlando
Known for its antique shops, annual arts festivals and great eats, Mount Dora sits just a 45-minute drive north of Orlando. Hop on the over-the-top sushi bandwagon with sushi burritos, sushi donuts and sushi pizza at WAVE Asian Bistro, or step into the past at the Mount Dora History Museum, housed in a 1923 fire station downtown. And don't miss out on the thrifting day of a lifetime at Renninger's Vintage Antique Center or the Village Antique Mall.

Sanibel Island

4 hours and 33 minutes to Orlando
Enjoy a bike ride or a comfortable stroll under covered walkways that trace in and out between neotropical foliage, on the city’s main thoroughfare for shopping and dining. Along the way, stop by Periwinkle Place, a 41,240-square-foot shopping experience, home to the original Chico’s, the award-winning Blue Giraffe and more than two dozen other shops.

St. Petersburg

2 hours and 23 minutes from Orlando
A little over two hours west of Orlando — past Tampa and the end of I-4 — is downtown St. Pete, known as “Sunshine City” for its Guinness World Record–holding 768 days of consecutive sunshine. That record provides plenty of reasons to play outside, but if you’re looking to escape the heat, the city has enticing indoor offerings as well. Explore the mind and works of Salvador Dali at the Dali Museum, or get lost in the Sunken Gardens, a living garden home to some of the oldest tropical plants in Central Florida.

Sarasota

3 hours and 5 minutes to Orlando
This Gulf Coast city is just about three hours from the City Beautiful and it’s so charming, you may never want to leave. Sink your toes into its powdery sand, and you’ll definitely start making plans to return. Clown around at the perfect-for-all-ages Ringling Circus Museum or spend a Saturday morning downtown at the Sarasota Farmers Market for locally roasted coffee, treats and a stroll.

Ormond Beach

1 hour and 8 minutes to Orlando
This tiny Volusia County beach town is just about an hour northeast of Orlando, located on Florida's east coast. Walking along Granada 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 or pop onto Romano Beachfront Park to catch some rays.

Fernandina Beach

3 hours and 4 minutes to Orlando
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 architecture on display. 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.

Boca Grande

4 hours to Orlando
Boca Grande has long attracted the wealthier set as a natural seaside haven, but its Old Florida charm is for everyone to enjoy. The Port Boca Grande Lighthouse is the oldest structure on the island where this beach village is found. If you’re seeking good fishing, try the Boca Grande Pass, one of the deepest natural channels in Florida. Downtown, you can explore the well-preserved historical sites of the Gasparilla Inn. If you want to visit a local eatery, stop by PJ’s SeaGrille to enjoy their artistically presented seafood and enjoy the homey environment, which includes patio seating.

Apalachicola

5 hours and 22 minutes to Orlando
Apalachicola’s Market Street has many charming local shops in this quaint Cape Cod-adjacent fish town. 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 Seafood, which specializes in Apalachicola oysters and seafood classics.

Flagler Beach

1 hour and 19 minutes to Orlando
Flagler Beach is famous for its six miles of uninterrupted beaches. After exploring the beach and the nearby parks, visit the Central Avenue shops that sell locally made clothes and pottery. The Flagler Beach Municipal Pier is a popular spot for fishing, and there’s a great deal of green space like the Bulow Plantation Ruins Historic State Park, 150 acres of scenic trails leading to a monument of Florida’s history with sugar plantations on the east side. The farmers market is every 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.

Dunedin

2 hours and 40 minutes to Orlando
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.

Atlantic Beach

2 hours and 30 minutes from Orlando
South of Jacksonville and north of St. Augustine about two and a half hours from Orlando is a little town called Atlantic Beach. Drive until you reach the beach, and you’ll find rows of pastel-colored cottages mixed with a little history and a lot of local life and delicious food. Brave the waves, sun yourself on the shore or get immersed in Florida history at the Beaches Museum. Then treat yourself to some homegrown eats like Key lime pie from Pie Heaven Bakery Cafe or a pop-tart donut from The Mini Bar.