Welcome to historic old town of Italian city district in Venice, Florida.

7 Cutest Small Towns In The Gulf Coast

Seaside was drawn up from scratch in the early 1980s, its pastel cottages and picket fences laid out as the first model of New Urbanism. In Ocean Springs, the painter Walter Anderson left behind murals and a family pottery that still turns out work downtown. Fairhope blooms with planted flower beds along every sidewalk above Mobile Bay. A few of these Gulf Coast towns fill up with festivals and spring-training crowds. The rest trade nightlife for oyster docks, bike paths, and bayou trails.

Venice, Florida

The fishing pier at Venice, Florida.
The fishing pier at Venice, Florida.

Venice wears the title Shark Tooth Capital of the World. The little black fossils wash up across its beaches by the thousands. Downtown is a short walk of low storefronts and outdoor tables a few blocks back from the water. Ciao Gelato has been spinning artisan gelato and sorbet on Venice Avenue since 2009. For dinner, Prime Serious Steak butchers its cuts in an open room you can watch from your table.

Restaurants near the beach in Venice, Florida.
Restaurants near the beach in Venice, Florida. Editorial credit: Linda White Wolf via Shutterstock

The beaches stretch for miles down the barrier island. Caspersen holds the quiet end, backed by scrub instead of condos. It is the easiest place to fill a bag with teeth. Regulars wade in with long-handled scoops they call Venice snow shovels. Sunset is best caught from the long pier near Venice Beach. Bring a kitchen colander if you want to sift without renting gear.

Orange Beach, Alabama

The white-sand beach at Orange Beach, Alabama.
The white-sand beach at Orange Beach, Alabama.

Orange Beach has white sand on one side and a back bay full of marinas on the other. The center of town is The Wharf, a strip of shops and restaurants under a tall Ferris wheel you can spot from the highway. In September the town hosts Freedom Fest at The Wharf, a fall arts-and-crafts weekend of vendors and music.

Charter boats head out of Perdido Pass for the day. The back bays are calm enough for paddleboards and slow pontoon afternoons. Anglers chase the big tournaments that dock at The Wharf marina through the summer. When the sand gets crowded, the bayous and inlets behind town give you somewhere gentler to put in.

Apalachicola, Florida

Downtown Apalachicola, Florida.
Downtown Apalachicola, Florida.

Apalachicola grew up as an oyster town. It still tastes like one. Raw bars stand a block from the docks and shuck what the boats bring in that morning. The old port district is on the National Register. The town counts more than 900 historic homes and buildings dating to the 1800s. A self-guided walking map from the visitor center loops you past cotton warehouses and Victorian houses under the live oaks.

A street scene in downtown Apalachicola, Florida.
A street scene in downtown Apalachicola, Florida.

John Gorrie lived here. He patented the first mechanical refrigeration in 1851 in an effort to cool fever patients. A small state museum downtown tells his story. The restored Dixie Theatre puts on plays through the winter months. Each November the town holds the Florida Seafood Festival, the state's oldest maritime celebration. The weekend brings oyster-shucking contests and the blessing of the fleet.

Seaside, Florida

Downtown Seaside, Florida.
Downtown Seaside, Florida. Editorial credit: Felix Mizioznikov via Shutterstock

Seaside looks designed, because it was. Builders laid it out in the early 1980s as the first model of the New Urbanism movement. Think pastel cottages and picket fences on streets narrow enough to make cars feel like guests. The town square gathers around an open-air amphitheater that puts on live music on warm nights. Lunch comes from Airstream Row, a line of vintage silver trailers turned into food counters.

Just west, Grayton Beach State Park protects a stretch of dune-backed shore and a campground for anyone wanting to stay over. The Timpoochee Trail follows Scenic 30A past Seaside and the other beach hamlets for about eighteen paved miles, flat and easy on a bike. Rent one in town and you can pedal to a different settlement for coffee and be back before dinner.

Ocean Springs, Mississippi

Downtown Ocean Springs, Mississippi.
Downtown Ocean Springs, Mississippi. Editorial credit: Carmen K. Sisson via Shutterstock

Ocean Springs lives on art more than anything else. The painter Walter Anderson rowed out to a barrier island to work alone. A museum here holds his murals and watercolors. His family's Shearwater Pottery still turns out pieces nearby. Downtown is a few blocks of galleries and small restaurants under arching live oaks. The first full weekend of November, the Peter Anderson Arts and Crafts Festival takes over the whole place as the biggest art festival in the state.

Ocean Springs, near Biloxi in Jackson County, Mississippi.
Ocean Springs, near Biloxi in Jackson County, Mississippi.

The town edges Biloxi Bay on the eastern side of the Mississippi coast. Small parks and beaches line Front Beach Drive. East of downtown, the Davis Bayou section of Gulf Islands National Seashore opens up trails and a marsh boardwalk good for spotting herons. Casinos glow on the water a short drive west toward Biloxi, if that is the kind of night you are after.

Dunedin, Florida

Welcome sign in Dunedin, Florida.
Welcome sign in Dunedin, Florida.

Dunedin (say it done-EE-din) put Florida's craft beer on the map. Dunedin Brewery opened in 1996 as the state's first microbrewery. Seven more have crowded into the small downtown since, close enough that a brewery crawl on foot is the standard Saturday. The Pinellas Trail cuts straight through, so most of the taprooms stand a block off the path. Between pints there are cafes and a Scottish-leaning main street.

Dockside on a sunny day in Dunedin, Florida.
Dockside on a sunny day in Dunedin, Florida.

The Toronto Blue Jays hold spring training at TD Ballpark in town. A grapefruit-league ticket is cheap and close to the field. Out at the end of the causeway, Honeymoon Island State Park gives Dunedin its beach. A passenger ferry crosses to undeveloped Caladesi Island.

Fairhope, Alabama

The Mosher Castle in Fairhope, Alabama.
The Mosher Castle in Fairhope, Alabama. Editorial credit: Carmen K. Sisson via Shutterstock

Fairhope perches on a low bluff over Mobile Bay. The town leans into flowers the way other places lean into beaches. The sidewalks downtown are lined with planted beds the city tends all year. A little brick-and-iron courtyard called the French Quarter gathers a cluster of shops around a fountain. Mr. Gene's Beans has been scooping ice cream and pulling coffee here since 1993. The thing to order is the Fairhope Float, frozen yogurt blended with coffee and whipped cream.

The Municipal Pier reaches a quarter-mile into the bay, ending at a rose garden and a small restaurant. The bay itself sometimes pulls off something strange called a jubilee. Fish and crabs crowd the shallows on summer nights and people wade out with buckets. Mobile Bay opens straight into the Gulf, so the water carries the same salt and the same evening light.

Cute Without Trying

The cutest Gulf Coast towns got that way by accident. The look is a byproduct of working waterfronts and old downtowns nobody paved over for parking. Venice has handed out shark teeth for generations, and Apalachicola has shucked oysters even longer. The newer arrivals fit the same slow pace without forcing it, whether that is a brewery crawl in Dunedin or a Ferris wheel over the back bay in Orange Beach. None of them perform cuteness. They just do the ordinary things well, and the word takes care of itself.

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