8 Towns In Florida With the Best Downtown Areas in 2024

Florida is famous for its sunny weather, beautiful beaches, and bustling theme parks, drawing over 120 million tourists each year. But beyond the well-known attractions, Florida also has numerous charming small towns perfect for vacations and getaways. Here are eight towns in Florida with wonderful downtown areas waiting to be explored in 2024.


Situated on the Gulf of Mexico in Southwest Florida, Naples is renowned for its high-end shopping and cultural attractions. Founded in the 1880s and named after the Italian city, Naples boasts a similar climate and beautiful bay location.

Downtown Naples, with its ritzy boutiques, art galleries, and gourmet restaurants on Fifth Avenue South and Third Street South, is a delightful area to explore. This year, Naples celebrates the 100th anniversary of the Naples Pier with special events.

St. Augustine

Located on Florida’s northeast coast, just 40 miles south of Jacksonville, St. Augustine is the oldest continuously occupied European settlement in the US. Founded in 1565 by Spanish explorer Pedro Menéndez de Avilés, the town’s historic downtown area is like a living museum with its Spanish colonial architecture and 19th-century buildings.

Key attractions include the Castillo de San Marcos, a 17th-century Spanish fort, and the pedestrian-only St. George Street with its shops, restaurants, and historic sites.

Winter Park

Often overlooked by those heading to Orlando’s theme parks, Winter Park offers a sophisticated escape with its ritzy homes, luxury shopping, and rich history. Founded in the late 19th century as a winter resort for wealthy northerners, this picturesque community features upscale boutiques, art galleries, and sidewalk cafés along Park Avenue.

Central Park hosts outdoor concerts and art festivals, and Winter Park is also home to Rollins College and the Charles Hosmer Morse Museum of American Art, which houses the world’s most comprehensive collection of works by Louis Comfort Tiffany.

Winter Garden

Just a 30-minute drive from Winter Park, Winter Garden boasts historic charm and brick-lined streets. Originally a citrus farming town, it has transformed into a popular tourist and retirement spot.

Downtown Winter Garden is home to the Garden Theatre, the Plant Street Market, and the Winter Garden Heritage Museum. The West Orange Trail, a 22-mile paved rail trail, offers opportunities for hiking and biking, while Lake Apopka is a favorite spot for bass fishing.

Key West

Famous as the southernmost point of the continental US, Key West is known for its laid-back atmosphere, vibrant nightlife, and rich history. Duval Street, the heart of downtown Key West, is lined with restaurants and colorful bars like Margaritaville.

The star attraction is Mallory Square, where people gather each evening for the sunset celebration with street performers and a party atmosphere. Key West also celebrates Hemingway Days in July, marking the 125th anniversary of the writer’s birth in 2024.

Palm Beach

An island town on Florida’s southeastern coast, Palm Beach is synonymous with luxury and old-world glamour. Founded by oil tycoon Henry Morrison Flagler, Palm Beach has long been a winter playground for America’s elite.

Downtown Palm Beach, particularly Worth Avenue, features boutique shops, art galleries, luxury yacht sales rooms, and high-end realtors. The Norton Museum of Art will host a major exhibition celebrating Florida’s artistic heritage this year.


Located in Central Florida between Orlando and Daytona Beach, DeLand was founded in 1876 and named after its founder Henry Addison DeLand. The Downtown DeLand Historic District is home to 68 historic buildings, including the Museum of Art-DeLand and the Athens Theatre.

The Stetson Mansion, one of Florida’s first luxury estates, is nearby, as is Stetson University, Florida’s oldest private college.


Known as the “little town that time forgot,” Micanopy is the oldest inland town in Florida, founded in 1821. Downtown Micanopy is like stepping back in time with its well-preserved commercial buildings from the 1800s, many now housing antique and boutique shops.

The Herlong Mansion, a bed and breakfast built in 1845, is a charming place to stay. Nearby, the Paynes Prairie Preserve State Park offers opportunities to view bison, wild horses, and over 270 species of birds.

The Final Word

These eight delightful towns offer unique opportunities to experience the best of Florida without the crowds. From ritzy shopping in Naples and Palm Beach to the historic streets of St. Augustine and Micanopy, each location contributes uniquely to Florida’s appeal.

Visiting one or more of these towns in 2024 is a must for anyone looking to explore the Sunshine State’s diverse and charming downtown areas.

Leave a Comment