When people think of Florida, it’s usually the big stuff—Miami’s nightlife, Orlando’s theme parks, or the white sand beaches in the Keys.
But there’s a whole side of Florida most folks totally miss.
We’re talking about towns with unique architecture, historic streets, charming waterfronts, and small-town stories that stick with you long after your trip.
Some of these spots are tucked away inland, others are sitting pretty on the coast, and a few are so unique they feel like movie sets (because, in some cases, they are).
So if you think you’ve seen all of Florida—think again.
Here are 8 underrated towns that bring the charm, the weird, and the kind of stories you’ll be telling long after your trip’s over.
1. Mount Dora
Mount Dora is a small lakefront town in Central Florida, about 40 minutes northwest of Orlando, and it’s packed with charm and old-timey vibes.
It’s known for its antique shops, the 35-foot-tall Mount Dora Lighthouse, and festivals like the Mount Dora Arts Festival that draws up to 200,000 people every February.
You can stroll along the historic downtown streets lined with 1800s-style buildings, hop on a seaplane tour over Lake Dora, or take a sunset cruise on the Dora Canal, which is packed with mossy cypress trees and gator sightings.
There’s even a popular 2-hour ghost tour of downtown, where you stroll through the historic streets as actors bring local legends and spooky stories to life.
2. Apalachicola
Apalachicola is all about salty air, seafood shacks, and small-town grit with Gulf Coast flavor.
It’s tucked away in Florida’s panhandle at the mouth of the Apalachicola River, where it meets Apalachicola Bay, and has a reputation for some of the best oysters in Florida.
You’ll find shrimp boats docked along the working waterfront, weathered brick buildings turned into cool shops and bars, and the historic Gibson Inn from 1907 still standing proud on the corner.
Grab fresh oysters at Lynn’s Quality Oysters, then walk it off with a sunset stroll along Riverfront Park where the views are unreal and the pelicans always show up for a photo op.
3. Dunedin
Dunedin brings the beachy, artsy vibes with a bit of Scottish flair, yep, bagpipes and all.
It’s on Florida’s west coast, just 10 minutes from Clearwater, and it’s known for its cute walkable downtown, craft breweries like Dunedin Brewery (the oldest microbrewery in Florida), and its big annual Scottish Highland Games.
You can hop on the Pinellas Trail for a bike ride, chill at Honeymoon Island State Park with its 4 miles of sandy beaches, or ferry over to Caladesi Island—one of the few untouched barrier islands left in Florida.
There’s also a mural with an octopus motif downtown, which is part of Dunedin’s many public artworks, so it’s worth snapping a photo if you spot it.
4. Micanopy
After Dunedin’s beachy buzz, Micanopy slows things way down in the best possible way.
Located just 15 minutes from Gainesville, this tiny town is known as “The Town That Time Forgot,” and it’s packed with antique shops, moss-draped oak trees, and old Florida charm.
You can wander Cholokka Boulevard for vintage treasures, then swing by Pearl’s Country Store for BBQ and browse books at the cozy Micanopy Library, which looks like something out of a storybook.
Movie fans, fun fact: Doc Hollywood with Michael J. Fox was filmed here, and many of the town’s historic spots still capture that on-screen charm.
5. Punta Gorda
Punta Gorda brings waterfront living and bike-friendly streets with a laid-back, coastal twist.
It’s located right on Charlotte Harbor at the mouth of the Peace River in Southwest Florida, just 30 minutes from Fort Myers.
It’s got a super cool Harborwalk that stretches 2.5 miles along the water with scenic views, tiki bars, and the chance of spotting manatees if you’re lucky.
The town is full of murals, palm trees, and historic spots like the A.C. Freeman House, and you can even ride a free loaner bike from the city’s yellow bike program to explore it all.
Fishermen’s Village is the main hangout spot with shops, live music, and boat tours—and if you’re into sunsets, the ones from Laishley Park are straight-up stunning.
6. DeLand
DeLand keeps the energy going with a mix of college-town charm, street art, and some seriously cool history.
It’s about 30 minutes from Daytona Beach, and it’s best known for being the home of Stetson University, where you’ll find Florida’s oldest college buildings and a campus that looks like a movie set.
Downtown is packed with locally owned shops, some murals and public art to explore, and spots like Trilogy Coffee, where students and locals hang out over iced lattes.
Just a short drive away, you’ve got Blue Spring State Park, where hundreds of manatees gather in the crystal-clear spring during the winter.
7. Opa-locka
Opa-locka flips the script with wild architecture and one of the most unusual backstories in Florida.
It’s just 20 minutes from Miami, and the town features several Moorish Revival buildings featuring domes, minarets, and arches that look like they belong in an Aladdin movie.
There were originally over 80 buildings with names like Sultan Avenue and Ali Baba Avenue, thanks to a 1920s developer who was obsessed with Arabian Nights, though only a fraction of them still stand today.
It’s a quick detour off the main Miami routes, but if you’re into super unique places and offbeat history, this one’s a total gem.
8. Stuart
Stuart brings you straight to the water with small-town vibes and serious sailboat energy.
It’s on Florida’s Treasure Coast, where the St. Lucie River meets the Atlantic, and it’s proudly known as the “Sailfish Capital of the World.”
Downtown Stuart is super walkable, with colorful shops, waterfront restaurants, and a riverwalk that’s perfect for catching live music at Rock’n Riverwalk on Sundays and maybe even spotting dolphins in the nearby waters.
You can hop on a kayak tour through the mangroves, visit the Florida Oceanographic Coastal Center, or just chill at Bathtub Beach, where the reef keeps the waves calm and snorkel-friendly.
Related Posts
