St. Augustine, Florida. Editorial credit: Sean Pavone /

These Small Towns In Florida Have The Best Downtown Areas

With the unique natural features and historical significance of the towns attracting the visitors initially, it is the downtown area that comprises the area of gathering at the end of the day. These nine towns have the best downtown areas in the state of Florida.


Naples, Florida, USA downtown skyline at dusk.
Downtown of Naples, Florida, at dusk.

Naples is set in southwestern Florida on the Gulf of Mexico at the edge of Big Cypress Swamp. Established as a winter resort in the late 1880s, it was named after the Italian city to attract newcomers, while the arrival of the railroad and the construction of the Tamiami Trail running from Naples to Miami aided in populating the area. Tourism is the mainstay of Naples, while the citrus industry adds to the economy, and the large retiree population signals stability and quaintness of the city. The cultural mecca on the Paradise Coast, Naples, is home to sugar-sand beaches lining the long coastline and the tropically infused downtown and historic streets, such as the Third Street South and Fifth Avenue South. The eye-catching decorated pastel-hued buildings with cascading blooms house many upscale shops, bars, restaurants, and Italian-style patio cafes for people-watching. The outdoor lovers will love the fresh air and the colors of the Caribbean Gardens comprised of a botanical garden to please all senses, and the zoo, especially beloved by families with kids. The Collier County Museum is 5-acre (2-hectare) historical park in the city. The miles of beaches and the 1,000 feet (300 metres) long fishing pier call out for scenic strolls and all the water fun imaginable. 


DeLand, Florida
Persimmon Hollow Brewery and other shops in downtown DeLand street view. Editorial credit: SR Productions /

Part of central Florida, the historical city of DeLand, includes a walkable downtown worthy of wandering around. The countless adorable boutiques, vinyl record shops, antique shops, and restaurants to suit any taste set inside historic buildings please the eye with their aesthetic facades. The restored vintage Florida Victorian Architectural Salvage (1926) is known for a far-reaching clientele of lovers to repurpose architectural artifacts, with over 8,000 square feet of incredible architectural finds. There are the Persimmon Hollow and Hyderhead Brewery for an atmospheric evening, while the wine-lovers will rejoice in the Elusive Grape. As the area's only meadery, the Abbey Bar and the Odd Elixir are famed for their quintessential craft. For a wholesome experience of sipping one's way through DeLand and West Volusia, the renowned Cool Craft Trail comprises tastings of brews, meads, coffees, wines, and more. The DeLand Naval Air Station Museum, part of the DeLand Airport, delights the history buffs with its WWII history memorabilia. The nearby Blue Spring State Park is the winter home to a large population of Florida's manatees, where one can have a refreshing swim along the lined oak trees dripping in Spanish moss.

Key West

Key West downtown
Downtown area of Key West. Editorial credit: Markus Haberkern /

Key West's four-mile (6.4km) long by two-mile (3.2km) wide island comes with an incredibly rich downtown area and a sun-drenched beach bounded by crystal-clear waters for scuba diving, sailing, and snorkeling. The English corruption of Cayo Hueso, meaning "Bone Islet," the town was named after Spanish explorers finding human bones. Gifted to a Spanish army officer, Juan Pablo Salas by the crown in 1815, who sold it to the Americans, the town acted as a base of operations against pirates before getting destroyed by a fire in 1886. Since demonstrating a move for independence with protests against the imposition of a roadblock on the Overseas Highway in 1982, the self-declared Conch Republic celebrates its day every April. There is a unique blend of Cuban, West Indian, Bahamian, and American cultures in the atmosphere and the architecture on the streets. The patchwork of palm-fringed streets lined with conch-style houses beautifies the compact downtown area with a tropical vibe. Former vacationers include Ernest Hemingway, Tennessee Williams, and ornithologist John James Audubon who left their essence in the 19th-century wooden homes preserved as landmarks. The town continuously inspires artists, writers, and those preferring less conventional lifestyles to come and create, especially during the annual Hemingway Days Festival in July. The city also hosts the Fort Zachary Taylor State Historic Site, the Key West Aquarium, and three museums on shipwrecks and industry.


Dunedin, florida
Trolley driving through main St. in Dunedin, Florida. Editorial credit: Garrett Brown /

Incredibly atmospheric, Dunedin comes with kitsch Jolley Trolley trams carousing around the lively streets lined with colorful buildings for the famed postcard-perfect looks of the town. Initially settled by the Scots in 1852, the name is the Gaelic interpretation of the word for Edinburgh, "Dùn Èideann." The many streets with names nodding at the Scottish heritage are dotted with numerous pubs serving authentic food and craft beer with a complementing old-country vibe for the richest Scottish experience. More culture can be absorbed at the Dunedin Celtic Music festival and the Craft Beer Festival, integral to the town, revealing traditions through open celebrations of affairs through lights, colors, sound, authentic grub, and more beer. 

Key Largo

Key West, Florida
Tropical beach and pier on sunny beach in Key Largo, Florida Keys islands.

Known as Cayo Largo, meaning "long islet," Key Largo is the largest of the Keys in the Florida Keys archipelago, at 33 miles (53 km) long. The "easy-breezy" island town is connected by overseas U.S. Highway 1 to the mainland. A few miles offshore, the living coral reef makes it a highly-demanded tourist spot known as the "Diving Capital of the World," attracting thousands of scuba divers and sport-fishing enthusiasts. The kayakers and eco-tourists enjoy its proximity to the famous Everglades National Park, while those seeking cultural mingling can visit the Caribbean Club built in 1938. Although mostly filmed on Warner's set, the namesake film of 1948 earned the town its initial recognition. The 10,000-some residents spread over the large land area for an un-crowded paradise with a small quaint town feel and tropical environment. After tourism, the plantations of key limes aid the economy while adding the tropical vibe. Having formed as an exposed, fossilized remnant of a coral reef during a high tide that was uncovered and eroded during a subsequent ice age, the town has visible fossilized corals and smooth, eroded limestone "caprock" at the surface. The first underwater park in the nation, the Pennekamp Coral Reef State Park, contains the largest formation and the only living coral barrier reef in the continental United States. 

Tarpon Springs

tarpon springs, florida
Tourist and locals shopping at the historic beach downtown of Tarpon Springs. Editorial credit: /

Discovered in the early 20th century by Greek settlers who made the thriving industry out of the plentiful natural sponge in the sea, they set up commercial spots and engraved their culture and traditions into what Tarpon Springs is today. The town was named after the fish breed, plentiful in the waters around. The historical influence can be seen in the stores selling the natural sponge, while its whitewashed buildings, narrow winding streets, and loud markets selling all kinds of goods showcase the Greek influence. As the only town with pronounced Greek roots for hundreds of miles around, its authentic restaurants are known to serve some of the best Mediterranean cuisine in the region. 

St. Augustine

St. Augustine, Florida, USA town square and fountain.
Town square and fountain in St. Augustine, Florida.

Known for the cobbled streets and centuries-old Moorish and Spanish colonial buildings of its Historic District, St Augustine may just be the most aesthetic town in the United States. As the nation's oldest, continuously settled city, it was founded upon the arrival of the Spanish explorer Juan Ponce de León in search of the legendary Fountain of Youth in 1513. In 1965, Pedro Menéndez de Avilés established the city upon destroying the French colony, naming it after the bishop of Hippo. The Spaniards occupied the city for 256 years except from 1763 to 1783, when the state was under England's possession. Becoming part of the United States in 1821, the culturally-rich city maintains its historic charm, enchanting the visitors with the jaunty orange-and-green Old Town Trolleys, quaint street cafés, and hidden courtyards. The national monument grand Castillo de San Marcos, as the oldest masonry fort in the United States built in 1672–95 near the southern tip of the peninsula, is the Spanish empire's remaining symbol. The many Spanish colonial buildings and sites have been restored, while the main museums are the Lightner Museum, the St. Augustine Lighthouse and Museum, and the Government House Museum. 


Stuart florida
The historic downtown area of Stuart, Florida.

Stuart comes with a historically charming downtown brimming with shops, restaurants, boutique hotels, and a gorgeous waterfront. Having weathered many hurricanes and storms, the House of Refuge at Gilberts Bar (1876) is the sole survivor from those times, offering an insightful journey into the past. Serving to house shipwrecked sailors along Florida's East Coast, it is run by the United States Lifesaving Service, reminiscent of those who lived hardscrabble lives to help the shipwrecked sailors. As the Sailfish Capital of the World, the town is a popular wintertime destination for sport-fishing enthusiasts on the Gulf Stream off the coast. Known as the "Speedy Gonzales of the sea," the sailfish leap and dive continuously when free, putting on a fierce fight when hooked. The struggle to rear one in makes a real spectacle and a highly-demanded experience that can take hours to win the battle and land the magnificent creature in the boat. The town features many props commemorating the sea-fighters and shops selling memorabilia, while the locals tell century-old tales of their fishing for sails experience. 

These downtown areas, complete with a tropical vibe of the state, showcase the town's personality, culture, and historical significance. The many shops and restaurants complete with aesthetically pleasing facades diversify one's stay while eating out on an atmospheric restaurant patio or shopping for a special souvenir to bring home.

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