Its waterfront isn’t the center of industry it was in the mid-19th century, but some of the brick warehouses once devoted to cotton production remain – shop for clothing and other gift items at Grady Market for a taste – and the river’s influence is ever-present. Oyster boats run in place of cotton-laden steamboats. Shrimp and blue crab are tasty here, too. Though the town boasts more than 900 historic sites, it’s an easy walk among most of them.
Rivers run near it – the Chipola to the west, the Apalachicola to the east. Grab a paddle, or a tube, to glimpse limestone bluffs and experience area shoals – a particularly adventuresome one along the Chipola River Canoe Trail is known as “Look and Tremble Falls.” Venture into history at the Panhandle Pioneer Settlement, an impressive collection of original and replica structures featuring 19th-century log cabins, a farmhouse and a school. The working farm here produces sugar cane and its own syrup, and annual quilt shows and peanut boils capture the essence of Northwest Florida.
Anglers revel in the area’s bays and grassy flats, which reveal species from tarpon to trout; sun-celebrants and shell-seekers enjoy natural respites such as Dog Island, accessible only by boat. Back in “civilized” Carrabelle, the Camp Gordon Johnston Museum commemorates soldiers who completed their amphibious training here, including D-Day veterans. Oyster shacks and an annual Riverfront Festival highlight the town’s maritime identity, as does the renovated Crooked River Lighthouse, erected in 1895.
Holmes Creek, a spring-fed creek, flows through here with canoes and tubes (boating and fishing are popular, too). Falling Waters State Park stages some drama within its 100-foot-deep, 20-foot-wide sinkhole; when water levels are sufficiently high, a waterfall crashes inside. The annual Panhandle Watermelon Festival sweetens the scene at the Washington County Agricultural Center.
In 1929, the Old Spanish Trail opened to enable the ultimate transcontinental road trip, connecting San Diego to St. Augustine by way of cities well- and less-known, including Crestview. Main Street throws various events (a cruise-in car show, fall festival, barbeque and Veterans Day parade). A May Day Festival centers on Allen Park, established by the Okaloosa Negro Civic Club in the 1950s, and the Carver-Hill Museum, which chronicles the history of the local African-American community.
Reviving a century-old tradition, DeFuniak Springs hosts the annual Florida Chautauqua Assembly. Attendees gather at the renovated 1909 Chautauqua Hall of Brotherhood, which presides over perfectly round Lake DeFuniak. Chipley Park, also known as Lake DeFuniak, charms with lighted piers that end in gazebos, what is likely the oldest operating library in the state (established in 1886) and the Walton County Heritage Museum, which occupies a restored train depot.
The “world’s luckiest fishing village,” as the residents like to call it, was first established by New England fisherman Leonard Destin in the 1840s. What started out as a small fishing village has grown into a popular vacation destination. Visitors flock to its emerald-green waters, bright white sand beaches, upscale and outlet shopping complexes (the Silver Sands Factory Stores claims to be “the nation’s largest designer outlet center” based on number of designer-name stores), elegant restaurants, premier resorts and condo rentals. Fishing and seafood are still popular; Destin Fishing Rodeo and Destin Seafood Festival draw big crowds each October.
Fort Walton Beach
Not everyone knows that Fort Walton Beach hosts its own Mardi Gras. It’s a fun, Florida-style spin on the renowned revelry, but at its heart, this city’s all about the water. Ultra-green Gulf waves lap at blinding-white shores where dunes, resorts and water sports abound. The Boardwalk on nearby Okaloosa Island is a family-friendly attraction, and Florida’s Gulfarium lets you watch dolphin and sea lion shows and peer into large-scale aquariums. History gets serious at the Indian Temple Mound Museum downtown and at Eglin Air Force Base’s Air Force Armament Museum, where you can view vintage aircraft for free.
This may be South Walton’s original community from the 1800s, but Grayton Beach carefully balances history and culture. Sand dunes resemble snow-capped hills guarding quiet sands, and dense pines and oaks shroud aged wooden homes conjuring up a time when the pace here was even more easy-going. Make time to explore the trails and shores of Grayton Beach State Park. Colorful cottages all in a row conceal galleries and whimsical boutiques near much-talked-about restaurants.
You can feed giraffes, view twin tamarinds and take in acre after acre of free-roaming animals along the Safari Line express at the Gulf Breeze Zoo. Or, look for blue herons, brown pelicans and five-lined skinks inside the Naval Live Oaks Area (and headquarters) of the Gulf Islands National Seashore.
On the surface, Marianna is all antiques and 19th-century relics. St. Luke’s Episcopal Church, scene of the Civil War Battle of Marianna, still stands. Beneath the town, caverns (both water-filled and dry) invite exploration. Tours at Florida Caverns State Park reveal limestone stalactites and stalagmites – you also can camp and fish here, and the multi-use trails are popular with horseback riders, cyclists and walkers.
Mexico Beach represents sun, sand and surf on an intimate scale. Cast from the Mexico Beach Fishing Pier or Mexico Beach Canal Park. There are plenty of charters in town, too, and area waters conceal fish-filled reefs to the satisfaction of both divers and anglers. The seafood is as fresh as you’d expect. Sample it, with a glass of wine in hand and artwork all around, at the annual Mexico Beach Art and Wine Festival.
Blackwater River State Forest reveals trails along its waterway and Juniper, Coldwater and Sweetwater creeks (watch for pitcher plant bogs). Also see the town’s 1912 Imogene Theater, Gothic Revival-style St. Mary’s Episcopal Church and the West Florida Railroad Museum.
In a community this size, a handful of restaurants and long stretches of beach (12 miles, precisely) are all you need. Fishing and staging the quintessential day at the beach are top to-dos along these family-friendly shores.
Panama City and Panama City Beach
These towns have a beach persona that coaxes out the carefree in all of us. Attractions combine the stuff childhood is made of: go-karts, water slides and miniature golf (kitsch is alive and well at the circa-1959 Goofy Golf), while Gulf World Marine Park and ZooWorld are educational. St. Andrews State Park was once an America’s Best Beach pick, and it features diving, snorkeling, surfing and fishing. Underwater, an intricate system of artificial reefs and shipwrecks once earned the area the nickname “Wreck Capital of the South.” Seafood shacks and oyster bars serve up fresh eats almost everywhere you look.
Pensacola and Pensacola Beach
From sky to sea, there’s much to see here. Overhead, the Blue Angels practice from mid-March to mid-November (watch from the viewing area at the National Naval Aviation Museum). History dominates at street level. Take a guided tour of 19th-century homes and the 1832 Old Christ Church at Historic Pensacola Village, or stroll beneath the oaks to the wooden gazebo at Seville Square. There’s ample water sports activity and classic beach fun to be had along Quietwater Beach Boardwalk, but you can also access the hushed Gulf Islands National Seashore here. For divers, the world’s largest artificial reef, retired aircraft carrier USS Oriskany, lies just offshore.
With Gulf Islands National Seashore and Perdido Key, Big Lagoon and Tarkiln Bayou Preserve State Parks in proximity, Perdido Key protects some of the beach’s most fragile and magnificent assets: wispy sea oats, critical dunes and nesting birds and sea turtles. Enjoy hiking, crabbing and surf casting; fishing charters are always available. And, yes, Cajun-style steamed oysters, live music and an annual mullet toss can be found at the Flora-Bama Package and Lounge.
Port St. Joe
Florida’s first Constitutional Convention was held here in 1838, but the area’s legacy proves more natural than political. T.H. Stone Memorial St. Joseph Peninsula State Park, another America’s Best Beach pick in Northwest Florida, protects some of the state’s oldest and tallest sand dunes. Charters and marinas speak to Port St. Joe’s fishing sensibility, and a charming collection of buildings shares its 20th-century history (hint: lumber has a lot to do with it). Constitution Convention Museum State Park will fill you in on 19th-century happenings.
Santa Rosa Beach
Inside Eden Gardens State Park, the Wesley House’s stately columns and wrap-around porch transport you to its turn-of-the-century heyday. Grandfatherly oaks and ornamental gardens decorate the grounds, and a notable collection of Louis XVI furniture accents the home’s interior. Topsail Hill Preserve State Park and Point Washington State Forest take you back to nature. Bike the paved roadway to the park’s beach and fishable dune lakes; go off-road cycling or hiking inside the 15,000-acre forest.
Spend time in Seagrove Beach fishing or admiring the distinct ecology. Deer Lake State Park tempers its salty beachfront with fresh coastal dune lakes, which occur only along Florida’s Gulf Coast. The park borders Point Washington State Forest, where the Eastern Lake Bike/Hike Trail meanders through a sandhill habitat marked by an airy canopy of longleaf pines. Still, this is a South Walton community – you needn’t venture far to find beach cottages, shops and eateries.
You know it by its aesthetic: skinny streets, white picket fences and close-quartered homes painted as if to match the sky, sand and sea. The result is a calming community where concerts ring out from the amphitheater, art walks highlight local galleries and boutiques and a seasonal farmers’ market provides all you need – and all within walking (or biking) distance.
St. George Island
Cross the bridge from East Point to reach St. George Island. Vacation homes, and water, define the barrier isle. The Gulf, Apalachicola Bay and St. George Sound beckon anglers, paddlers and beachcombers. St. George Island State Park captures the island’s peacefulness along miles of dune-dotted beach.