10 Old Town Florida Destinations that Bring History to Life

Beyond the rollercoasters and resorts lies another side to the Sunshine State - a world of cobblestone streets, historic monuments, and picturesque small towns. For families looking to slow down a little this holiday and soak up some of that timeless charm, these destinations spread throughout Florida bring history to life. And in years yet to come, will let you recall your treasured holiday memories… 

North Florida 

St Augustine 

Starting off strong, St Augustine stands proudly as Florida’s oldest city. Founded by Spanish settlers in 1565, here you will discover architecture dating back hundreds of years - beautifully showcased in the 17th century Spanish stone fortress, Castillo de San Marcos.  

The city also boasts record breakers with the oldest wax museum, the oldest wooden schoolhouse, and the narrowest street in America. Timeless charm is felt around every corner and if you’re looking for fun ways to explore, the ghost tour is a great option. Adding a playful touch of mystery, it’s one that families of all ages will remember long after their holiday ends. 

Cedar Key 

For timeless charm, this hidden gem on Florida’s Gulf Coast offers a blend of natural beauty, rich history, and a vibrant arts scene.  

What used to be a bustling port in the 19th century is now a dream escape for nature loving families. There is a wealth of beaches, nature trails, and water sport options. A popular activity is to hire a kayak and paddle to the Cedar Keys National Wildlife Refuge, home to 800 acres of diverse ecosystem.  

Back on land, you can get a slice of history at Cedar Key Museum State Park or indulge in locally sourced seafood at the town’s restaurants.  

Fernandina Beach 

Fernandina Beach is known as a treat for the eyes, with its Victorian architecture, pastel storefronts, and golden sands. But don’t let its beachy picturesque exterior fool you, as there is over 400 years of history beneath the surface.  

This is an ideal location for families looking to mix laid-back beach days with heritage. Explore the enchanting Historic District, home to over 50 blocks of preserved 19th-century buildings, or visit Fort Clinch State Park, where rangers dressed in period uniforms recreate life during the Civil War. Kids will be sure to get a kick out of climbing the brick-walled fort and watching the cannons fire during re-enactments. 

Central Florida 

Winter Garden 

Just twenty minutes from the buzz of Orlando’s theme parks lies the delightful Winter Garden. The beautifully restored Downtown is brimming with local cafes and boutique shops. Rub shoulders with the locals at the popular Saturday Farmers Market or grab an ice cream from one of the charming family run ice cream shops.  

If you’re looking for something a little more active, one of the most memorable experiences to do is cycle the West Orange Trail, a 22-mile stretch through several towns, including plenty of rest stops along the way. This provides an excellent blend of sunshine, scenery and shared moments that make family holidays truly unforgettable. 

Mount Dora 

Often referred to as the New England of the South for its rolling hills and New England style architecture, this city is nothing short of stunning. Lake Dora, home to Florida’s only inland freshwater lighthouse, is the city’s centrepiece, but all around it you will find unique shops, art galleries, and cafes.  

Be sure to pay a visit to Mount Dora History Museum to learn all about the area’s past. Mount Dora is also famous for its lively calendar, so look out for events and festivals that take your fancy throughout the year, with each one offering memorable moments that showcase the town’s charm and community spirit.  

Tarpon Springs 

A cultural treasure unlike anywhere else in Florida, Tarpon Springs has the highest concentration of Greek heritage in the United States. Known for its historic sponge docks, the town still celebrates the traditions of the Greek sponge divers who settled here in the early 1900s.  

Families can watch sponge-boat demonstrations, browse the colourful waterfront shops, and indulge in fresh pastries and traditional dishes at the many Greek bakeries and restaurants. It’s one of our favourite places for making history fun for kids. 

South Florida 

Key West 

Blending Caribbean vibes with a rich Indigenous history, Key West is the southernmost point of the continental United States. Follow the pastel streets and you will find yourself at the home of famed writer, Ernest Hemingway.  

Then explore the lively Duval Street, historic seaport, or Cass Marina, a neighbourhood filled with luxury properties. Families will also love the nightly celebration at Mallory Square, where you can be entertained by jugglers and musicians before gathering to watch the sun descend into the ocean like a painted masterpiece. 

Naples 

Naples is a thriving upscale city renowned for its pristine white sand beaches and sophisticated dining and shopping. Old Florida elegance can be found in the charming Historic District, home to the iconic landmark, Naples Pier, as well as art galleries, antique shops, and historic homes dating back to the late 19th century.  

We love continuing our journey through time at the Naples Depot Museum, where restored railway carriages and exhibits transport guests back to the railroad boom of the roaring twenties.  

Sanibel 

With unspoilt natural beauty, Sanibel offers a quieter slice of the Sunshine State. It’s famous for its seashell-strewn beaches, making it one of the best places in the world for shelling.  

As well as the abundance of seashells there’s plenty more waiting to be unearthed, including scenic cycling paths and the historic Sanibel Lighthouse, standing tall since 1884.  

And for any wildlife enthusiasts in the family, don’t miss your chance to see J.N. “Ding” Darling National Wildlife Refuge, where gentle boardwalks lead to mangrove swamps filled with birds and marine life. 

Ready to create memories wrapped in history? Our Florida Package holidays await.