The Most Picturesque Towns In Florida
The sun kisses and breathtaking scenery elevate the Sunshine State to the top of the most visited in the US. Florida is a literal hotbed for culture, history, and adventure in a tropical atmosphere with diverse nature, from the Everglades and citrus groves to the dunes and soft white sand beaches, and beyond the fabulous coastline, where coral reefs and wild islands inspire boundless ecotourism.
From Anna Maria's unspoiled beauty to the untouched landscapes in Steinhatchee and idyllically designed Seaside, these are the nine (very different) most picturesque towns in the Sunshine State. Each offers a unique take on Florida's captivating beauty and charm, elevating it with unobscured views and one-of-a-kind attractions to appreciate the warm sentiment and beauty on a whole other level.
Anna Maria
Accessible via highway from Bradenton or Sarasota, Anna Maria Island is a serene, seven-mile-long barrier island on Florida’s Gulf Coast with three coastal cities (Anna Maria, Holmes Beach, and Bradenton Beach) and vivid Gulf views. With the town of Anna Maria as your base, the island's award-winning string of beaches delivers a visually captivating backdrop and the faraway feel that you desire. From the well-equipped Manatee Public Beach to the secluded Bean Point Beach, the gentle waters lapping up the sandy, wide shores are ideal for play in the turquoise surf.
Anna Maria transforms you along the northern edge on a relaxing escape, with its artsy beach town vibes and a laid-back feel downtown, with attractions like the Artists Guild Gallery. You can swim, snorkel, and stretch out, book a dolphin spotting tour, or explore for seashells and fossilized shark teeth. Explore the City Pier Park and get through a slew of downtown shops before stopping for a seafood haunt, drinks at a sandbar, or a box of donuts to enjoy along the sands at sunset.
Fernandina Beach
Fernandina Beach is Florida's northernmost coastal city on Amelia Island. Having flown eight different flags—hence the Isle of Eight Flags—over its illustrious past, the charming Victorian-era city with a marina and alluring beaches nods at a long-desired location. Today, the historic shrimping village blends the remnants from each of the ruling nations in and around downtown, like the waterfront Fernandina Plaza Historic State Park, across the street from the house where Pippi Longstocking was filmed.
Its beautiful marshes, diverse parks, and beaches for every style inspire you to seize every waking hour after the sensational sunrise looking east. Escape into the wild along Egan's Creek Greenway Trail with gator views. Fort Clinch State Park features an epic 1864 fort with guided tours, camping, and wildlife trails. Just a stroll from the eclectic shops, arts, and dining scenes downtown, Seaside Park draws picnickers and beach bums with scenic boardwalk access.
Key West
Accessible from the mainland via the Overseas Highway, the last Florida Key is the southernmost point in the state and in the continental US. Known as Hemingway's haunt, you can explore the writer's house, studio, and gardens, stroll past the Truman Little White House, and peek into the aquarium or the Key West Shipwreck Museum. Key West welcomes you with a waterfront downtown, with a historic lighthouse turned museum and booming nightlife along Duval Street.
Key West is one of the state's most visited towns and for good reason, with its pastel-hued, conch-style houses, plus the shipwrecks and coral reefs that make it a diving and snorkeling destination. There's plenty of naval history and adventure to explore before the daily Sunset Celebration at Mallory Square. Hop on a sightseeing cruise or book a fishing trip, then dive into the Key West Butterfly and Nature Conservatory, a glass-enclosed, plant-filled habitat for interactive walks among winged species.
Rosemary Beach
Mimicking its absolutely beautiful quartz sand beaches along Highway 30A, this elegant village puts a sparkle into everything, like the European-inspired Rosemary Beach Inn at its heart. There's something distinctly European about Rosemary's architecture and eye-catching designs that make it possibly even more picturesque "beyond" the private beach. Rated top for location, the Village of South Walton Beach offers reasonable vacation rates a block from the all-beloved 30A Farmers' Market.
Visitors enjoy the upscale yet relaxed atmosphere and stunning backdrop along the cobblestone streets on foot or along the bike lanes, with welcoming shops, inviting galleries, and award-winning restaurants. Who other than tourists can truly appreciate the new flavors and unexpected attention to detail with such genuine excitement, or the unbeatable views at Pescado Seafood Grill's Rooftop Bar? The town is surrounded by public beach access points, such as the nearby Inlet Beach.
St. Pete Beach
St. Petersburg's little brother is a real charmer to the west, with a picturesque swath of award-winning beaches. Pass-a-Grille Beach, the retro southern neighborhood, boasts a long, undeveloped public beach, ideal for water sports, to perfect your parasailing, practice stand-up paddleboarding, and pick up windsurfing or kiteboarding. Its rave-worthy soft, white sands and terrific upkeep give way to the warm Gulf of Mexico waters, an atmosphere that envelops you in merciless views.
To the north, Upham Beach Park is backed by protected dunes, with scenic rock jetties for dolphin sightings and light surfing. Meanwhile, the heart of the barrier island pulses with exciting venues, top hotels, and restaurants through the Corey Avenue district, defined by its funky specialty shops, galleries, and eateries to taste local fare. Choose Crabby Bill's picnic table or the rooftop bar for the good vibes and laid-back atmosphere to indulge in seafood and second-to-none Gulf views.
Seaside
This Emerald Coast gem is the birthplace of New Urbanism, focused on creating walkable, functional, and environmentally conscious spaces. Tucked along scenic Highway 30A, Seaside's thoughtful accents lure sightseers, design buffs, and families on a quick escape with escapades through parks. Grayton Beach State Park boasts camping and a coral reef offshore, with fishing, paddling, biking, and hiking in between, like the one-mile Dune Lake Trail. More ambitious hikers can opt for the 18-mile Timpoochee Trail.
Featured in “The Truman Show,” the town's Pleasantville vibes resonate against the pastel cottages and small-town enticements lining the downtown bike lanes. From shopping, dining, and art venues, the serene waterfront views beckon for a breezy bike ride along the clear, emerald-green waters lapping up its white-sand beaches. Finally, at the Airstream Row, you can pick up gourmet hot and cold snacks or enjoy a beverage from a line of retrofitted vintage Airstream trailers next to a tree-canopied walkway.
Steinhatchee
Just 70 miles west of Gainesville, this historic fishing village is literally a walk in the park, at the entrance of Deadman's Bay along Florida's Gulf Coast. Home to under 1,000, this authentic town douses you in "real Florida" vibes, among the last of such developments, to experience the one-of-a-kind "coastal country living." Surrounded by small farms and horse pastures, the Steinhatchee Wildlife Management Area surrounds the town with beautiful woods, ideal for horseback riding, hiking, fishing, or biking amidst cypress swamps and floodplain forest.
Two trails converge at the beautiful Steinhatchee Falls along the river, with a swimming hole for a refreshing dip. Meanwhile, the charmingly rustic and uncrowded downtown is a stone's throw away from the marinas and tiki bars along the waterline. As the scallop capital of the world, fishing is a widespread recreation, with snook, redfish, or trout aplenty. It is a great way to get out and explore the waters, with every kind of fresh seafood hauled in daily to the waterfront restaurants for a picturesque feast.
Venice
Incorporated in the 1880s, Venice contends as the most picturesque place on Florida’s Gulf Coast, blending new and retro with unique nature and architecture. The European allure and palm-lined boulevards give way to 14 miles of beaches, plus fossilized prehistoric shark teeth finds. Whether you're after the soft white sands, surfing, or family saltwater adventures, Venice Beach is a certified Blue Wave Beach, telling of its clean environs, ideal waves, and reef diving a quarter-mile offshore.
In addition to the famed Venetian Waterway Park Trail, this idyllic city is also the Shark Tooth Capital of the World, inspiring long walks along Caspersen Beach. And yes, the Historic Downtown nods at the Italian city namesake, with shopping, arts, and an architectural backdrop, like the 1950 Venice Theatre. There are countless ways to soak in the picturesque vibes, from swimming in the clear turquoise Gulf surf to fishing and sunset strolls along the iconic 700-foot Venice Fishing Pier.
Vero Beach
This elegant city on Florida’s Atlantic Coast is all kinds of dreamy, with 26 miles of beaches, a historic downtown, and a sophisticated arts and entertainment scene of opera, theater, and ballet. There are plentiful ways to explore and soak in the picturesque vibes, be that a relaxing, enriching, or shoptastic retreat, with beautiful local artwork at the Vero Beach Museum of Art. Take the scenic pathways of McKee Botanical Garden, a mix of native and exotic plants through the quiet, 18-acre oasis.
The crowd-free sandy shores and a lively downtown translate into a stress-free getaway in a serene environment. South Beach Park is popular for picnics with picturesque views. In addition to surfable waves, you can paddle or cruise past town along the Indian River Lagoon. Just 14 miles north, Pelican Island National Wildlife Refuge is a real gem along the Treasure Coast with native bird life, secluded nature trails, and miles of undeveloped sandy beaches to spot cute shorebird species.
Whether you are exploring Rosemary's European allure along the cobblestoned streets, Key West's shipwrecks, reefs, and nightlife, or Vero Beach's idyllic outline along the intercoastal waterway, each makes it feel like there's no other place you'd rather be than soaking in the tropical blend akin to a nirvana.
These nine captivating island towns and historic cities envelop your every sense in an atmosphere charged with picturesque vibes. Certainly, you're not chasing the scenery; it finds you along Steinhatchee's untouched trails through the "real Florida" or surfing in the Shark Tooth capital.
