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Anna Maria City Pier in Anna Maria, one of the cute small towns in Florida.

Looking for a cute small town to visit in Florida? You’ve got your pick! Even though high-rise development is famous for creeping along the coasts of Florida and residential communities are moving further inland, there are still many areas of the Sunshine State that retain small-town charm. Whether you want to visit these areas for a day trip, a weekend stay, or for move-in potential (#RemoteWork), you’ve got your choices.

Our list of seven cute small towns in Florida is by no means a complete list. These are some of our faves, but we can expand the list in the future. Plus, there are many other charming small towns right here in Florida that we’d still like to visit. Let us know if you know of other cute small towns in Florida you’d like us to feature.

Without further ado, let’s dive in.

7 Charming Small Towns in Florida

A trolley tour in St. Augustine going down a scenic street with Spanish moss.

St. Augustine

Location: Northeast Florida, about 45 minutes south of Jacksonville, 2 hours south of Orlando, and 3 hours away from Tampa

America’s oldest city aka St. Augustine, established in 1513, offers a ton of history along with nearby beachy fun. The downtown commercial area features St. George Street, a busy pedestrian-friendly street with stores and restaurants. Nearby is Castillo de San Marcos, a Spanish fort constructed in 1695. Take advantage of Old Town Trolley Tours to get an enjoyable, complete lowdown on St. Augustine’s history. Take pictures at the Bridge of Lions (complete with lion statues) that crosses over the Matanzas River. Matanzas means “massacre” in Spanish, so that gives you some sense of the violent history in St. Augustine (explorers and pirates and ghosts, oh my!). In fact, the city is said to be haunted, and there are both walking and trolley ghost tours at night. When you’ve had enough history, you’re just minutes away from beautiful St. Augustine Beach, the St. Augustine Lighthouse (it’s haunted, too) and Vilano Beach. The St. Augustine Alligator Farm Zoological Park is a pretty cool destination as well. Tip: For an early morning treat, get to the St. Augustine Pier to watch the sunrise.

More reading: Here Are Six Things to Do When You Visit St. Augustine

Picturesque hanging flowers in downtown Venice, Florida.


Location: About 30 minutes south of Sarasota and 90 minutes from Tampa

Sarasota on Florida’s Gulf Coast is more well-known than Venice, but Sarasota continues to grow like wildfire. So, if we’re talking about small towns, we’ll focus this time on Venice, which has somewhat of an Italian flair just like the city of the same name in Italy. Venice is a retiree mecca, with its cute downtown, a vibrant weekly farmers market, sunny weather, and popular beaches. In fact, Venice is known as the “Shark Tooth Capital of the World” because of the millions of shark teeth that have been found on its beaches through the years, including Venice Beach (great pier) and Caspersen Beach. Within downtown, you’ve got a couple of popular breakfast spots, including Croissant & Co., which had a waiting line outside one recent weekend. You’ll also find several Italian restaurants and Abondanza, an Italian deli/store. Tip: Sea Pleasures & Treasures in the downtown area sells your typical beach souvenirs but also has an interesting display of shark teeth and alligator heads.

More reading: Shark Tooth Hunting in Venice, Florida: Answers to All Your FAQs

7 Ways to Search for Shark Teeth in Venice

Anna Maria Island is famous for its beaches.

Anna Maria Island

Location: A little over an hour south of Tampa, about 2 1/2 hours from Naples

Travel + Leisure has named Anna Maria one of the best small towns in Florida, but we locals have known that for a long time. What was once an Old Florida secret has now become a must-see destination on Florida’s Gulf Coast. Located near Bradenton Beach and near Sarasota, Anna Maria Island has gorgeous beaches and a family feel. You can enjoy a drink right on the beach at places like The Sandbar or cast a line at the Anna Maria City Pier or the Rod ‘N’ Reel Pier, both of which also have restaurants on site. The piers look onto Tampa Bay and Skyway Bridge, a picturesque large bridge that carries traffic from Manatee County into St. Pete. Visitors to Anna Maria enjoy “the good life” with regular bikes and walks and shopping at areas like Pine Avenue. Tip: As word has gotten out about Anna Maria, traffic has increased. Leave early in the day for less traffic and to make it easier to find parking, especially if you’re going to places like Bean Point at the tip of the island. If you don’t have any luck, make it over to nearby Holmes Beach, Bradenton Beach, or Coquina Beach, where parking is more abundant.

More reading: 9 Free Things to Do on Anna Maria Island

The U.S. and Florida flags, spotted outside a shop in Micanopy, Florida.


Location: About 20 minutes from Gainesville and 90 minutes from Jacksonville

Micanopy (pronounced mic-ah-no-pee) is a small town near Gainesville (home to the University of Florida) that’s filled with a few antique shops, some cute restaurants, a historical society, and the Herlong Mansion, a bed and breakfast. It’s truly a small Southern town with a lot of history. Yet if you want to expand your experience, visit Paynes Prairie Preserve State Park, which also has a Micanopy address. The expansive preserve has wild horses and bison, several trails, a visitor center, and a cool observation tower where you just may catch a view of the buffaloes roaming. Travel + Leisure also named Micanopy one of the best Florida small towns. Tip: You may be able to spot gators at Paynes Prairie, but keep in mind that some trails get flooded and may be closed during the rainy season in the summer.

More reading: Things to See and Do in Micanopy, Florida

What to Know Before You Visit Paynes Prairie Preserve State Park

One of the views when you spend time in Cortez, Florida.


Location: About a half hour from Sarasota and an hour south of Tampa

Florida is known for its fresh seafood and fish, but there aren’t that many authentic fishing villages still around. Cortez is a real fishing village, located just minutes away from Anna Maria Island. Cortez is not your destination if you’re looking for shopping or sunning yourself on the beach, although you can get all of that just minutes away on Anna Maria Island or at Bradenton Beach. Instead, go to Cortez for history and some really good seafood. Star Fish Company and Tide Tables are two standouts in Cortez for your shrimp and grits or grouper sandwich, and you may spot commercial fishing boats as well as fishing charters and recreational boaters while you eat. The commercial fishermen are busy catching mullet, grouper, and stone crab, according to this interesting article about Cortez. Make the Florida Maritime Museum part of your visit for the lowdown on the town’s history. Tip: Celebrate Cortez all you want during its annual Cortez Commercial Fishing Festival, typically held in February and attracting 20,000 people daily.

More reading: Commercial Fishing Still a Way of Life in Cortez

Find boating, good food, and sunny skies in Tarpon Springs, Florida.

Tarpon Springs

Location: About 45 minutes north of Tampa and about two hours from Ocala

Opa! Tarpon Springs celebrates its Greek and sponge diving heritage. This seaside town has a long history of sponge divers who dive for–you guessed it–sea sponges, used in cosmetics and for bathing. That, along with the long history of Greek natives who came to call Tarpon Springs home, give Tarpon Springs a special flare. On a sunny day, with Greek music piping out of some stores, you may even convince yourself you’re in Greece. Save room for a Greek meal or a dessert like baklava. Saint Nicholas Greek Orthodox Cathedral is a gathering place for the local community and is interesting to see.

More reading: Here Are 5 Things to Do in Tarpon Springs

Golf carts outside The Gasparilla Inn and Club in Boca Grande.

Boca Grande

Location: About an hour and 20 minutes south of Sarasota; about two hours north of Naples

Boca Grande, located on Gasparilla Island and north of Fort Myers, is less well known than places like Fort Myers or Sarasota, but we think they like to keep it that way. This exclusive waterside enclave has welcomed well-known residents and visitors, from University of Alabama head football coach Nick Saban to the Bushes (as in, the presidential family). Boca Grande is home to a walkable, quaint downtown area with some cute shops and restaurants as well as beach areas and a lighthouse. (Actually, there are two lighthouses in the general vicinity). The Gasparilla Inn is an upscale place to stay and features The Pink Elephant Restaurant and a few other places to eat. Boca Grande incurred some damage during Hurricane Ian in September 2022 but appears to have generally recovered.

More reading: 7 Things to Do in Boca Grande, Florida

Venice Beach, just minutes from downtown Venice, Florida. View from the Venice Pier.

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