12 Small Florida Towns Worth Visiting from Leesburg

Florida is known for its beaches, theme parks, and large cities, but some of the state’s most enjoyable destinations are the smaller towns scattered throughout Central and North Florida. Many of these communities have rich histories, charming downtown districts, waterfront parks, local restaurants, and attractions that make them perfect for a day trip.

One of the advantages of living near Leesburg is being within driving distance of dozens of unique Florida towns, many of which can be explored in a single day. Whether you’re looking for a relaxing drive, a scenic waterfront, historic architecture, local seafood, or simply a change of scenery, these destinations offer a glimpse into a side of Florida that many visitors never see.

1. Mount Dora

Distance from Leesburg: Approximately 20 minutes

Mount Dora may be one of the most well-known small towns in Central Florida, but it still manages to maintain its historic charm. Founded in the late 1800s, the town grew as a popular destination for visitors arriving by steamboat on the Harris Chain of Lakes. Today, its downtown streets are lined with brick sidewalks, historic buildings, boutique shops, and locally owned restaurants.

One of the most popular places to visit is the Mount Dora waterfront, where visitors can enjoy views of Lake Dora while strolling through Sunset Park and Palm Island Park. The town is also known for its festivals, including the nationally recognized Mount Dora Arts Festival and various seasonal events throughout the year.

Visitors can spend an afternoon browsing antique stores, grabbing lunch at one of the lakeside restaurants, taking a boat tour, or simply enjoying a walk through the historic downtown district. The combination of lake views and historic architecture makes Mount Dora one of the most enjoyable day trips from Leesburg.

2. Cedar Key

Distance from Leesburg: Approximately 2 hours

If you’re looking for “Old Florida,” Cedar Key delivers. Located on the Gulf Coast, this small island community feels worlds away from the busy highways and growing suburbs of Central Florida.

Originally a significant port during the 1800s, Cedar Key played an important role in Florida’s early development before railroads shifted transportation routes elsewhere. Today, that slower pace remains one of the town’s greatest attractions.

Visitors can explore Dock Street, browse art galleries, visit the Cedar Key Historical Museum, enjoy fresh Gulf seafood, or watch the sunset from the waterfront. Fishing and kayaking are particularly popular, and the town’s Gulf views make it one of the best sunset destinations in Florida.

Unlike many beach towns, Cedar Key has largely avoided large-scale development, helping preserve its unique character and small-town atmosphere.

3. Micanopy

Distance from Leesburg: Approximately 1 hour 15 minutes

Known as “The Town That Time Forgot,” Micanopy offers a glimpse into Florida’s past.

Founded in the early 1800s and named after a Seminole chief, Micanopy is one of Florida’s oldest inland towns. Large oak trees draped with Spanish moss create a picturesque setting that feels almost untouched by modern development.

The town became famous after serving as a filming location for the 1991 movie Doc Hollywood starring Michael J. Fox.

Visitors enjoy antique shopping, historic homes, bed and breakfasts, and nearby Paynes Prairie Preserve State Park. The downtown area is small but packed with character, making it an ideal destination for a relaxed afternoon.

4. Tarpon Springs

Distance from Leesburg: Approximately 2 hours

Tarpon Springs has one of the most unique histories in Florida. During the late 1800s and early 1900s, Greek immigrants established a thriving sponge-diving industry here, creating a community that still celebrates its heritage today.

The Sponge Docks remain the centerpiece of town, where visitors can learn about the sponge industry, browse Greek bakeries, and enjoy authentic Mediterranean cuisine.

A walk along Dodecanese Boulevard feels unlike anywhere else in Florida. Restaurants serve traditional Greek dishes, bakeries offer fresh pastries, and sponge boats line the waterfront.

For anyone looking for something different from the typical Florida tourist destination, Tarpon Springs is well worth the drive.

5. Apalachicola

Distance from Leesburg: Approximately 4 hours

While farther away than some other destinations on this list, Apalachicola rewards visitors with one of the most authentic coastal towns in Florida.

Once a major cotton-shipping port, Apalachicola became famous for its seafood industry, particularly oysters harvested from nearby waters.

The town’s historic downtown features beautifully preserved buildings dating back more than a century. Visitors can explore local shops, waterfront parks, museums, and seafood restaurants while learning about the area’s maritime history.

The slower pace and strong connection to Florida’s Gulf Coast heritage make Apalachicola feel entirely different from most modern beach communities.

6. DeLand

Distance from Leesburg: Approximately 50 minutes

Home to Stetson University, DeLand combines historic charm with a vibrant downtown atmosphere.

Founded in 1876, the city has maintained many of its original buildings and is known for having one of Florida’s most walkable downtown districts.

Visitors can explore the Museum of Art – DeLand, the historic Athens Theatre, and dozens of restaurants and shops. The nearby St. Johns River and Blue Spring State Park provide additional outdoor recreation opportunities.

DeLand strikes a nice balance between historic preservation and modern amenities, making it one of Central Florida’s most underrated destinations.

7. Winter Garden

Distance from Leesburg: Approximately 40 minutes

Winter Garden has experienced tremendous growth in recent years, but it has successfully preserved the charm of its historic downtown.

Originally an agricultural community known for citrus production, the town has transformed into one of the most popular gathering places in Central Florida.

Visitors enjoy Plant Street Market, the West Orange Trail, numerous restaurants, craft breweries, and seasonal events. The downtown area remains highly walkable and offers plenty of opportunities for shopping and dining.

Its proximity to Leesburg makes Winter Garden an easy choice for a quick day trip.

8. Crystal River

Distance from Leesburg: Approximately 1 hour 45 minutes

Crystal River is best known for its population of manatees, but there is much more to explore than wildlife viewing.

The town’s springs, rivers, and Gulf access have made it a favorite destination for boaters, anglers, and outdoor enthusiasts. The historic downtown area features local restaurants, shops, and parks that showcase the area’s natural beauty.

Visitors can take guided manatee tours, paddle crystal-clear waterways, visit Crystal River Archaeological State Park, or enjoy fresh seafood at one of the waterfront restaurants.

The combination of natural beauty and small-town character makes Crystal River one of Florida’s most appealing destinations.

9. Clermont

Distance from Leesburg: Approximately 30 minutes

Known for its rolling hills and chain of lakes, Clermont offers a landscape that surprises many visitors who assume all of Florida is flat.

Historically a citrus-growing community, Clermont has evolved into a popular destination for outdoor recreation. Waterfront Park, Lake Minneola, and the Clermont Chain of Lakes provide opportunities for boating, fishing, cycling, and walking.

The downtown area continues to grow while maintaining a friendly, small-town atmosphere.

Visitors looking for beautiful lake views and outdoor activities will find plenty to enjoy here.

10. Fernandina Beach

Distance from Leesburg: Approximately 2 hours 45 minutes

Located on Amelia Island, Fernandina Beach boasts a fascinating history involving Spanish, French, British, and American influences.

The downtown district features Victorian-era architecture, waterfront views, and a variety of restaurants and shops. The nearby beaches offer a quieter alternative to many of Florida’s more crowded coastal destinations.

Visitors can explore Fort Clinch State Park, stroll Centre Street, enjoy fresh seafood, or simply spend time on the beach.

The blend of history and coastal scenery makes Fernandina Beach one of the most interesting towns in Florida.

11. Inverness

Distance from Leesburg: Approximately 1 hour

Often overlooked by travelers, Inverness offers a relaxing small-town atmosphere surrounded by natural beauty.

The town sits near the Withlacoochee State Trail, one of Florida’s longest paved recreational trails, making it a popular destination for cyclists and walkers.

Visitors can enjoy parks, lakes, historic buildings, local restaurants, and outdoor recreation opportunities throughout Citrus County.

Its slower pace and welcoming community make it an excellent option for a relaxing day trip.

12. Tavares

Distance from Leesburg: Approximately 20 minutes

Known as “America’s Seaplane City,” Tavares has become one of Lake County’s most unique destinations.

Located directly on Lake Dora, the town embraces its aviation heritage while offering waterfront dining, parks, and recreational activities. Visitors can watch seaplanes take off and land throughout the day, adding a unique element to an already enjoyable lakeside setting.

Wooton Park serves as the heart of downtown, featuring walking paths, playgrounds, event spaces, and excellent lake views.

Combined with nearby Mount Dora and Eustis, Tavares makes for an easy and enjoyable day exploring the Harris Chain of Lakes.

Discover More of Florida

One of the best things about living in Leesburg is the ability to reach so many unique destinations within just a few hours. From historic downtown districts and Gulf Coast fishing villages to lakeside communities and hidden gems, Florida offers far more than theme parks and crowded beaches.

The next time you’re looking for a weekend adventure, consider taking a drive to one of these small towns. You may discover a new favorite destination, enjoy a memorable meal, or simply gain a greater appreciation for the diverse communities that make Florida such a fascinating place to explore.

And before hitting the road, stop by Ciggys4Less in Leesburg to stock up for the journey ahead. Whether you’re heading toward the Gulf Coast, exploring historic downtowns, or watching a sunset over the water, a little preparation helps make every day trip more enjoyable.