Here are 8 of the best downtown areas in Florida. See if your favorite made the list

Winter Park, Winter Garden, DeLand make the list

Winter Park (Winter Park)

The World Atlas released a listing of eight of the best downtown areas in Florida, with several Central Florida cities making the cut.

Florida is one of America’s most visited states and attracts over 120 million tourists every year, according to World Atlas. Whether it is due to the endless warm weather and beautiful beaches or the iconic theme parks, countless people make the trip to the Sunshine State.

However, there is more to Florida than the popular attractions and renowned climate. Some of the most notable offerings are the hidden gems, found in small towns sprinkled across the state. From the historic streets of St. Augustine, the oldest city in Florida, to the shores of Key West’s tropical paradise, there is no shortage of charming downtown areas to provide locals and visitors with a new place to explore.

Here is World Atlas’s list of the best downtown areas in Florida, giving you some new places to add to your travel regiment this summer.

Naples

Naples is a popular tourist and retirement destination, nestled in Southwest Florida on the Gulf of Mexico. The small town was named after the Italian city of the same name, due to its beautiful bay locations and similar climate, and was founded in the 1880s.

Defined by its world-class culture and high-end shopping opportunities, Naples’s downtown streets lead to the beach, famous for its breathtaking sunsets. The area is beautiful to explore on foot and reflective of the town’s wealth, consisting of artisan boutiques, art galleries and gourmet dining establishments.

St. Augustine

St. Augustine resides on the northeast coast of Florida and holds the title of being the state’s oldest city. Founded by Spanish explorer Pedro Menéndez de Avilés in 1565, St. Augustine’s historic downtown area is defined by its Spanish colonial architecture, European streets and 19th-century buildings.

There are several attractions in the downtown area, including the Lightner Museum and the Spanish fort Castillo de San Marcos built in the 17th century from coquina, a shell stone native to Florida’s east coast. The historic district also consists of St. George Street, a narrow European-style thoroughfare designed for pedestrian traffic only, which features artisan shops, specialty restaurants and famous landmarks.

This area is home to the renowned Nights of Lights that occurs each holiday season, from November to January. This annual event, a favorite of both locals and visitors, was listed in the top 10 holiday light displays in the world by National Geographic in 2012, according to Florida’s Historic Coast.

Shoppers in St. Augustine (WJXT)
Winter Park

Winter Park is a “picturesque community” located just north of Orlando that is known for its stylish homes and luxury shopping locations. Initially founded in the late 19th century as a winter vacation destination for wealthy northerners, the streets and buildings are indicative of the town’s elevated atmosphere.

Much of the downtown area revolves around Park Avenue, which is home to numerous upscale boutiques, art galleries, sidewalk cafés and fine dining options. The area around Central Park is additionally an ideal location for a stroll and where the town’s events are held, such as outdoor concerts and art festivals.

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Winter Park is also home to Rollins College, a private liberal arts school that has consistently topped the charts for the beauty of its campus, along with attractions such as the Charles Hosmer Morse Museum of American Art.

Photo of part of Park Avenue in Winter Park in June. (Winter Park)
Winter Garden

A vibrant lakefront community that initially started as a citrus farming town, Winter Garden is another Central Florida town that made the list. With its distinct historic charm and brick-lined streets, the downtown area of Winter Garden has a thriving arts and culture scene with upscale eateries, unique vintage shops, nature parks and museums.

Some of the notable attractions include the Garden Theatre, the Winter Garden Heritage Museum and the Plant Street Market, which offers an array of artisanal goods and culinary selections.

Photo of Winter Garden. (Copyright 2024 by WKMG ClickOrlando - All rights reserved.)
Key West

Famous for being the southernmost point of the United States, Key West is a small island town at the very tip of the Florida Keys. It is known for its tropical atmosphere, lively nightlife and rich history. Nicknamed the “Conch Republic” by those who call the town home, Key West is a favorite of both local Floridians and tourists alike.

Duval Street encompasses the downtown area and is famous for its specialty shops, restaurants and colorful bars. The town’s diverse artistic landscape has long been a preferred destination for artists, such as the famous author Ernest Hemingway. Mallory Square, at the end of Duval Street, is often the venue for street artists and musicians, who fill the coastal air with creativity and their own artistic aura as the sun sets behind the ocean.

Photo of Mallory Square in Key West. (Pixabay)
Palm Beach

Palm Beach is another island town, located on the southeastern coast of Florida. Characterized by its tropical elegance, pristine beaches and “old-world” glamour, Palm Beach is home to one of the highest densities of billionaires in the county, according to World Atlas. The city’s streets, lined with lavish mansions and landmarks of the Gilded Age, allow a perfect opportunity for sightseeing.

The downtown area consists mainly of Worth Avenue, which features designer boutiques, charming courtyards and art galleries placed right alongside high-end realtors and luxury yacht sales rooms. The Norton Museum of Art is a staple of the town, which showcases Florida’s artistic heritage through artworks inspired by the state’s unique landscape and culture.

DeLand

DeLand is a small town tucked in between Orlando and Daytona Beach. There are several quaint shops, restaurants and attractions to check out on Main Street while exploring the downtown area.

DeLand was founded in 1876 and consequently provides a rich storied landscape in the Downtown Historic District. This area in particular is home to 68 historical buildings, including the Museum of Art-DeLand and the Athens Theatre, where the charm of a classic American theater meets Italian Renaissance architecture. Another of the most prominent is Stetson University, the city’s private college, one of Florida’s first luxury estates and a 19th-century architectural masterpiece.

Downtown DeLand (Copyright 2024 by WKMG ClickOrlando - All rights reserved.)
Micanopy

Known as the “little town that time forget,” Micanopy is a very small town just south of Gainesville. This old, inland town was founded in 1821 and is defined by its rich history that predates the Second Seminole War.

The downtown area does not span very wide, but those who visit liken the experience to “stepping back in time.” This is due to its well-preserved antique buildings and architecture. One in particular is the Micanopy Historical Society Museum or the Herlong Mansion, which was built in 1845 with signature red bricks and is now a classy bed and breakfast. Many others are home to quaint vintage shops or boutiques.

Another must-see in Micanopy is the Paynes Prairie Preserve State Park. This vast wetland habitat is home to bison, wild horses and over 270 species of birds that visitors have the opportunity to see in their natural environment.


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About the Author

Kendal is a journalism student at the University of Central Florida. Born and raised in the Sunshine State, Kendal loves reporting on local and regional news in the Central Florida area. Her favorite coverage areas are breaking news, politics and environmental reporting. She joined ClickOrlando.com in June 2024.

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