These five Florida towns have a common thread running through them: They are each unique with walkable downtowns. Join the journey as we unpack five of Florida’s coolest small towns and share recommendations for the best things to do in each one.
Note that some of the information I share was obtained during a hosted visits. All opinions remain my own.
1. Stuart
You might know Stuart as the Sailfish Capital of the World, and rightfully so as the town almost pops at the seams during the winter months. Sportfishing enthusiasts flock to Stuart to try their hand at landing a sailfish or two.
Sailfish are plentiful in the Gulf Stream off the coast of Florida during the winter months. With a life span of 4 to 6 years, these predators are the Speedy Gonzales of the sea. Once hooked, these sea warriors put on a spectacular fight. The experience of fishing for sails will be the stuff of fishing stories for years to come.
Sailfish leap and dive continuously, and it can take hours to land one of these magnificent creatures. It is a thrilling experience to hook a sailfish and fight them — and eventually win the battle and land one in the boat.
Aside from fishing, Stuart has a quaint and charming walkable historic downtown filled with shopping, restaurants, a gorgeous waterfront, boutique hotels, and inns.
Carve some time out to visit House of Refuge at Gilberts Bar; it is a fascinating journey back in time. Houses of Refuge, run by the United States Lifesaving Service, were havens for shipwrecked sailors along Florida’s East Coast.
The House of Refuge at Gilberts Bar dates back to 1876 and has weathered many hurricanes and storms. Today it stands as the sole survivor and seeks to tell the story of the people who lived hardscrabble lives to help shipwrecked sailors.
2. DeLand
DeLand is located in the central part of Florida and has a history to share. The highlights of DeLand include a wonderfully walkable downtown.
As you wander the streets lined with adorable boutiques, vinyl record shops, antique shops, and restaurants housed in historic buildings, be careful. You may fall in love with the area!
One of DeLand’s most popular shops has a far-reaching clientele. Florida Victorian Architectural Salvage is a dream come true for people who love repurposing architectural artifacts. The shop is in a restored vintage 1926 building and houses over 8,000 square feet of incredible architectural gems.
After walking the cute downtown area, you’ll want something to quench your thirst. Walk over to Persimmon Hollow or Hyderhead Brewery for those who love beer. For a bit of a change, check out Odd Elixir at the Abbey Bar. Odd Elixir is the area’s only meadery. Wine lovers, don’t miss a visit to the Elusive Grape for a glass (or bottle) of wine.
DeLand has just debuted their Cool Craft Trail, which embodies brews, meads, coffees, wines, and more! Don’t miss this unique opportunity to sip your way through DeLand and West Volusia.
There are so many other gems in the DeLand area to discover! The DeLand Naval Air Station Museum is located at the DeLand Airport and is worth a visit if you are a WWII history buff.
For those who like a bit of spirited history, take a drive out to Cassadaga Spiritualist Camp. Cassadaga offers readings by onsite mediums and psychics. Many of them live onsite and have gone through rigorous training to become members of the Cassadaga community.
Get in touch with nature out at Blue Spring State Park. Blue Spring is the winter home of much of Florida’s manatee population. During the summer months, the spring provides a beautiful respite to the heat as you float down the natural spring lined with oak trees dripping in Spanish moss. The spring is a naturally brisk 72 degrees.
3. Apalachicola
If you are looking for an off-the-beaten-path destination where you can relax and simply be, you’ll find it in Apalachicola. This quaint Florida fishing village with the vibe of Old Florida offers wide, shady tree-lined streets with large homes dating back to the 19th and 20th centuries when Appalachicola was a thriving fishing and oystering area. Over 900 historic homes and buildings are in the Apalachicola area.
The town is perched right on Apalachicola River and Bay, one of the most undeveloped and ecologically diverse waterways in the United States. Several hotels overlook the channel, including the Water Street Hotel and the Consulate Suites. What better way to begin your day than sipping a cup of coffee as you look out over the waterway to see fishing boats slowly chugging their way out into the bay as birds lazily swoop overhead?
During the 19th century, Apalachicola was a thriving fishing port. The historic buildings housed ship chandleries, a sponge warehouse, and fishing net factories.
You will not need your car, so leave it parked. Take some time and wander the streets of Apalachicola. There are eclectic shops, boutiques, restaurants, art galleries, and bed and breakfasts located in the historic buildings that line the downtown streets.
The people are friendly and welcoming and love to chat and share their stories. Time slows down in Apalachicola, making it an ideal place to relax and enjoy the low-key pace. Plan a day of fishing, or explore the waterways by kayak, canoe, or sailboat. There are plenty of options for outdoor fun.
4. Fort Pierce
Located on Florida’s east coast, Fort Pierce is home to treasure hunters, a stellar farmers market, and an energetic downtown area that’s undergoing a renaissance. In 2011, Fort Pierce received the Great American Main Street Award from the National Trust for Historic Preservation.
Off Florida’s east coast from Stuart up to Sebastian are shipwrecks that have attracted treasure hunters. The most famous of these treasure hunters is Mel Fisher, who found a “carpet of gold coins” from the 1715 treasure fleet. The wreck sites also attract divers from across the world.
Fort Pierce attracted the eye of the U.S. Navy in 1942. It was seeking a home base for training the newly formed combat demolition teams. Fort Pierce fit the bill with its year-round temperate weather and isolated beaches. So in late 1942, the Naval Combat Demolition School was established in sleepy little Fort Pierce. From their humble beginnings as so-called frogmen, the U.S. Navy SEALS were born on the grounds of the training center site.
Today the U.S. Navy SEAL Museum located in Fort Pierce on North Hutchinson Island celebrates the frogmen’s heritage. For WWII history buffs, a visit to the museum is a must. Filled with memorabilia from World War II through modern-day skirmishes and battles, the museum has amazing exhibits that are always changing.
A not-to-be-missed statue: The imposing-in-stature Naked Warrior, who stands with fins in his hand, a face mask perched on his head, and a slate board with a pencil around his neck. The Naked Warrior guards the entrance to the museum. He is a tribute to all maritime commando units that set the capabilities and standards for today’s U.S. Navy SEAL teams.
Pro Tips: While in Fort Pierce, stop in and have a bite at Pickled Restaurant and Bar downtown. Serving up delicious Southern fusion delights with a twist, Pickled is a perfect spot for a relaxed lunch or dinner. For lovers of hard cider, don’t miss a stop at Pierced Cider Works. Using locally sourced fruits as the basis of their creations, Pierced is creating some unique sips.
5. Dunedin
Dunedin teeters on the edge of the Gulf of Mexico, and sparkling white beaches give way to the Gulf of Mexico’s glistening waters.
Just off the coast, you will find Caladesi Island. Caladesi is a barrier island, and it’s home to one of the top 10 U.S. beaches of 2020 according to Dr. Beach. Caladesi State Park is only accessible by water, making it one of the most pristine and untouched beaches along the Gulf Coast.
Honeymoon Island State Park is a paradise for birdwatchers. Beach lovers will love strolling the beach in search of the perfect shell on the water’s edge. Be sure to catch the sunsets from Honeymoon Island — they are spectacular!
For a more immersive marine-life experience, check out the Clearwater Marine Aquarium, just a short drive from Dunedin. You may recognize the aquarium from the movies Dolphin Tale and Dolphin Tale 2 that brought to the forefront Winter, a dolphin who became entangled in monofilament and lost her tail.
All types of marine life call the aquarium home. The most devious are the albino pelicans. These troublemakers kept sneaking out of their homes and frolicking on the deck, much to the delight of visitors.
Dunedin’s downtown is fun to window shop. There are gift shops, restaurants, ice cream shops, coffee shops, and more, all within a short walking distance of the waterfront. For even more Dunedin inspiration, consider The Best Things To Do During A Long Weekend In Beautiful Dunedin.
As you can see, no matter where you want to go in Florida, from the central part of the Sunshine State to the Gulf Coast, east coast, or west coast, there are plenty of fun, cool towns to pique your interest. These five Florida small towns are just the tip of the iceberg. Florida has lots of fun, funky, and relaxed small towns just begging for you to come and explore! See also: