If you stray a bit from Florida’s main tourist hotspots like Orlando or Miami, you’ll find a wonderland of picturesque towns full of natural beauty and historical charm. Blessed with unspoiled landscapes, palm-fringed beaches, and a contagious laid-back vibe, these small Florida towns are the ideal place to escape the bustle and hustle of popular cities and theme parks and instead, enjoy a day filled with sunshine, charm, and chilled out vibes.
Featuring a distinctly European vibe with a coastal twist, St. Augustine is one of the cutest cities in Florida and a must-visit for one simple reason: it’s the oldest city in the United States.
St. Augustine’s quaint streets and attractions bring to life the history of Florida, while also featuring modern entertainment and lots of beach goodness for those who like to mix things up. Think cobblestone streets, romantic squares draped in charming cafés, and a myriad of historical sights to explore throughout the day.
Start the day with a hearty breakfast at the many quaint coffee shops in the city center, explore the historical worth of Castillo de San Marcos, check out a few museums, climb to the top of St. Augustine Lighthouse for the most stunning views or simply spend the day relaxing at the white sandy beaches that span the city. You can see my full review of the things to do in and near the town here.
Crystal River is known for its manatees and clear springs, but the town itself shouldn't be overlooked! With manatee decor nearly everywhere you look, from the cafes to the mailboxes, it's certainly a cute place to stop for a photo op or two.
Most of the town's shops are locally owned and operated, and there's even a flea market right off of main street, so stop at Cattle Dog Coffee Roasters grab a green apple chai to go (that's a personal favorite) then head out for a stroll around town to discover the many hidden gems and maybe you will leave with an unconventional souvenir.
You have probably heard me mention Tarpon Springs a time or two on my social media, and I mean, rightfully so. I've not met anyone who's been here and not absolutely fallen in love. Sponges and authentic Greek cuisine--what more could you ask for out of a small town? Seriously though, for anyone who likes souvenir hunting, baklava, and sunset cruises, heaven is a place on Earth when you're in this small town just north of Tampa.
While I could go on for days describing everything I love about it here, there are no amount of words that can truly do this town justice--so I highly recommend a visit to see for yourself.
Not too far from Tarpon Springs is another small town with big Europe vibes. Dunedin, named after the Scottish town of Dunedin, is like the Scottish version of Tarpon Springs. Where everything is Greek there, switch it out for Celtic pride in Dunedin.
The main street offers many restaurants, souvenir and specialty shops, and cafes. The boat dock and marina are close by, giving residents and visitors alike a place to sit and watch the waves and boats lazily roll in.
The best part about Dunedin may be that it's home to one of the best beaches in all of the state, Honeymoon Island. I highly recommend spending some time at the beach then dusting off the sand in town for a bite of fresh seafood, then finishing the day off with sunset views over the marina.
Quite possibly the most famous island in the Florida Keys, Islamorada is located in the spot where barrier reefs, saltwater wilderness, and the nature of Everglades National Park meet.
The island is dubbed the sport-fishing capital of the world, but if fishing is not exactly your jam, there’s plenty more to keep you entertained during your visit.
Ocean adventures are king here (think snorkeling, sailing, and diving to name a few), but you’ll also find plenty of shopping, fine dining (seafood, we’re looking at you), and entertainment to keep you lingering a while longer (all with the prettiest views of white sand beaches acting as a backdrop, of course!).
Home to a picture-perfect waterfront, bustling entertainment, and vibrant neighborhoods, Palm Beach is a bit of a hidden gem in South Florida, but worth visiting if what you’re after is a bit of a luxury vibe and a burgeoning arts scene to your vacay.
Shop the designer boutiques along Worth Avenue, dine at trendy restaurants, or grab your bike and ride along the Lake Trail for a glimpse of the island’s lavish estates.
Tip: Don’t forget to check out what festivals are in town during your visit (seriously, Palm Beach’s calendar tends to be filled with fun activities!).
One of Florida’s biggest secrets, Matlacha is a picturesque little town that brims with candy-colored buildings and coastal village charm. Reminiscent of Old Florida but with a burst of colors splashing every scene, the main thing to do at Matlacha is to slowly stroll its streets in search of artsy stalls, fresh seafood, and laid-back beachy vibes.
Sanibel Island may be tiny, but what it lacks in size, it makes up for with wonderful things to do during your stay!
Thanks to the fact that it comprises gorgeous azure beaches, a national wildlife refuge, and hiking trails winding through marshes, Sanibel is your go-to if you’re into quiet vacations and a mix of beach fun and nature. Moreover, its downtown’s shabby chic vibes and casual style will have you wishing you could stay just a little longer.
Being one of the few islands that runs perpendicular to Florida’s coastline (most run parallel), Sanibel’s beaches are covered in shells. Shell-collecting has become the island’s claim to fame, and joining a “Sanibel Stoop” (as locals call the act of shelling) is a must-do activity while here.
Victorian vibes are the norm at DeFuniak springs. While there’s not a whole lot to do here, this cozy little town is perfect for a quiet vacation, especially if you’re into old-world charm beauty and nature. Seriously, you could easily dedicate a few days just to admiring this town’s enchanting architecture that has stood the test of time - grab your bike and travel Circle Drive Historic Center in search of stunning homes!
DeFuniak Springs has a pretty unusual claim to fame: it surrounds a perfectly circular spring-fed lake, which is one of only two perfectly symmetrical lakes in the world (the other one is set in Switzerland). The lake is freckled by pine trees and exquisite Victorian homes, making the entire scene look straight from a fairytale.
We hope this list of the cutest towns in Florida helped you choose a destination for your next escape! Even though some are more popular than others, they all guarantee a wonderful time combining beach, entertainment, and nature.
Is this France? Norway? Maybe Canada? Nope! Believe it or not, it's none other than the charming seaside town of Rosemary Beach. Featuring a brick road and unusual architecture, it's no wonder why this is a favorite spot for dates, weddings, and of course, honeymoons. But don't feel like you need to have a romantic outing to enjoy everything Rosemary Beach has to offer.
With cafes and eateries galore, some of which with exceptional views of the pristine Gulf Coast, you can easily get lost in a whole new world here, and with a postcard of main street you can totally trick anyone into thinking you're in a land far, far away.
Located in the greater Jacksonville area, Amelia Island is one of the most beautiful islands in the Sea Islands chain. While here, explore the island’s slightly ritzy vibes by strolling through Fernandina Beach’s charming Old Town district, check out historic shops spread all over, and try the island’s excellent foodie scene at the trendy restaurants that line the streets.
To top it off, the island brims with nature activities and thriving wildlife, all of which you can get to know on foot, on a kayak, or even on a charter boat!
Have you been to any of these small towns? Have any others you'd like to recommend? Tell me below in the comments!