Tourists walking in front of the La Concha Hotel and Spa in Key West.

10 of the Most Charming Small Towns to Visit in Florida

Florida is bordered by the Atlantic Ocean and the Gulf of Mexico, making it a hot spot for visitors. While the bigger cities like Orlando and Miami are the most well-known, plenty of charming small towns should be on any traveler's bucket list. Florida has a lot to offer: history, picture-perfect beaches, and miles of natural wetlands are just the beginning.

These ten towns are among the most charming and represent the best of what locals call "old Florida." Old Florida takes you to a different, simpler time. Beautiful scenery, friendly locals, and fresh seafood are the characteristics, and each of these towns offers that atmosphere and more.

Key West

Street view of the Main Strip in the Downtown City where all the bars are located in Key West, Florida
Street view of the Main Strip in the Downtown City where all the bars are located in Key West, Florida

Key West, the southernmost point in the United States, is a tropical oasis that receives its fair share of visitors yearly. It is a sportsman's paradise, with charters, anglers, and scuba divers setting out from Bud and Mary's Marina daily. Many famous people have called this island home over the years, most notably Ernest Hemingway, whose house has been preserved with authentic furniture and the descendants of his six-toed cats.

Entrance of Mallory Square in Key West, Florida
Entrance of Mallory Square in Key West, Florida, via Wangkun Jia /

The town is reached via the Overseas Highway, which introduces one to shockingly blue water and white sand, major draws for beach lovers. Aside from the Hemingway Museum, many historic sites exist here, such as Fort Zachary Taylor State Park, Truman Little White House, and Sloppy Joe's. This is a fun and quirky place where people are invited, nay, demanded, just to be themselves and soak in the history and the sun.

St. Augustine

People shopping in St. George Street in Saint Augustine, Florida
People shopping in St. George Street in Saint Augustine, Florida, via Andriy Blokhin /

St. Augustine, on the state's northeast corner, is the oldest town in the continental US. It was established in 1565, and many buildings and roads are the same today. The town is an eclectic blend of French and Spanish architecture combined with narrow streets for a wholly unique location.

The town is centered around the Castillo de Saint Marco, a Spanish fort built to protect Florida's trade routes and is now a National Monument. It is right across from St. George Street, a pedestrian only street in the heart of historic downtown. There are period-dressed actors for the live reenactments that intermingle with locals and visitors, giving St. Augustine an old-world yet fun atmosphere that is hard to find anywhere else.

Mount Dora

The colorful downtown area of Mount Dora, Florida
The colorful downtown area of Mount Dora, Florida. Editorial credit: Jillian Cain Photography /

Mount Dora is a quaint and elegant town in central Florida. Centered around Lake Dora, this historic town is known today as an antique hub. The Point Grantham Lighthouse sits on the shore of Lake Dora, and it is a nice place to visit, complete with picnic tables and pleasant lake breezes.

The historic downtown is ideal for walking. Along with the Modernism Museum, there is the Mount Dora History Museum, which is housed in a 1923 lighthouse. Charming inns will round out Mount Dora's experience, most notably the Lakeside Inn, a historic lakeside inn.

Anna Maria Island

Rod and Reel Public Fishing Pier on the Anna Maria Island.
Rod and Reel Public Fishing Pier on the Anna Maria Island.

Anna Maria Island is a gorgeous, laidback coastal town on the western end of Sarasota, on the Gulf Coast. It is known for its powdery sand beach, clear blue water, and unbelievable sunsets. Pine Avenue and Gulf Drive are the main thoroughfares through the small village, where most shops and dining options are available.

There are different little beaches along the island, and they all have something to offer. Coquina Beach and Bean Point are known for their unbelievable sunset views, while Holmes Beach is less populated. Holmes Beach rests at the crossroads where the Intracoastal Waterway meets the Gulf, providing brackish and saltwater fishing opportunities. Anna Maria is about as close as one can get to the Caribbean without leaving the US, and the beauty and atmosphere must be seen and believed.


Historic square shopping area in Seaside, Florida.
Historic square shopping area in Seaside, Florida. Image credit Kristi Blokhin via Shutterstock.

Seaside is a small resort community in northwest Florida. It was designed with late 20th-century New Urbanist architecture, including pastel-colored houses with white picket fences that lend a true beach feel to the town. The access points to the beach are marked with stunning pavilions flanked by palm trees.

The town is so picture-perfect that it was the setting for The Truman Show, starring Jim Carrey. Other notable attractions include Bud and Alley's Waterfront Bar and Grill, ideal for watching the sunset from the open-air top deck. Seaside is the idyllic beach town of yesterday, with a diminished number of high-rise buildings, franchises, and too much traffic. This town is meant for leisurely walks or bicycling, which allows one to soak in the laid-back beach vibes.

Vero Beach

Entrance to Vero Beach, Florida
Entrance to Vero Beach, Florida. Image credit Felix Mizioznikov via Shutterstock

Vero Beach is a barrier island on the Atlantic Coast, across from the Indian River Lagoon. It is centered around its natural beauty and preserves, including McKee Botanical Garden and Pelican Island National Wildlife Refuge. The 26-mile coastline is popular for golfing, fishing, and a sophisticated arts scene.

The Vero Beach Art Museum is a fun way to experience state and national art exhibits, including a sculpture garden. Live theatre venues like the Riverside Theatre Inc. and the Vero Beach Theatre Guild exemplify the art scene here. Vero Beach is a family-friendly beach town with nice sunrises and a relaxed environment.


Street view in Venice, Florida
Street view in Venice, Florida, via Andriy Blokhin /

Venice, the shark tooth capital of the world, is a small coastal town in southwest Florida. The Venice Fishing Pier is 700 feet long and one of the best spots for shore fishing. Some trails wrap around the Intracoastal Waterway, and Oscar Scherer Park offers kayaking, canoeing, and hiking opportunities among 15 miles of trails.

Along with the natural attractions, Venice has a historic downtown dating back to the 1920s, intermingled with mossy oaks for that authentic "old Florida" feel. Centennial Park is at the heart of downtown and offers free concerts. If visiting over the weekend, check out the Farmer's Market on Saturday mornings for fresh produce and seafood.


Aerial view of Captiva, Florida
Aerial view of Captiva, Florida

Captiva Key is west of Fort Myers, near its sister island, Sanibel. The two were connected until a hurricane in the early 20th century created the Blind Pass channel between them. As you approach the island over the Sanibel Causeway, you are greeted by tropical-colored water and white-sand beaches with low-lying buildings so as not to obstruct the view.

Things to do in Captiva include kayaking, shelling, and, of course, relaxing on the powdery beach. Sanibel is the seashell capital of the world, so there are plenty of opportunities to collect. Captiva Drive winds through the restaurants and shops lined by bougainvillea and goes to the downtown village. This quaint beach town has a throwback atmosphere perfect for a low-key time.

Boca Grande

View from above of large residential houses in island small town Boca Grande on Gasparilla Island in southwest Florida
View from above of large residential houses in island small town Boca Grande on Gasparilla Island in southwest Florida

Boca Grande is a small community on Gasparilla Island in Southwest Florida. The Port Boca Grande Lighthouse was built in 1890, and today, a museum dedicated to preserving its memory is located at Gasparilla State Park and is a popular draw for many visitors. Bicycling is fun here, and there is the Boca Grande Rail Trail, a six-mile bike trail running the length of the island.

As a bonus, kayak or motorboat to Cayo Costa, a nine-mile barrier island off the coast with an undeveloped shoreline, for a fun day of fishing. Lunch and dinner are best at the Gasparilla Inn and Club, built in 1911, which retains its old Florida charm. This island is pleasant off of North Fort Myers but feels miles away from the big city.

Rosemary Beach

Aerial view of Rosemary Beach, Florida, showcasing the beautiful turquoise waters of the Gulf of Mexico.
Aerial view of Rosemary Beach, Florida, showcasing the beautiful turquoise waters of the Gulf of Mexico.

Rosemary Beach is a planned community in northwest Florida. Its modern architecture has a classic beach town aesthetic, and it has been lauded as one of the most romantic towns in America. The cobblestone steps lead to the town center, known for its award-winning, sophisticated dining and boutique amenities.

Pescado Seafood Grill and Rooftop Bar offers unbeatable sun views while The Summer Kitchen and Cafe offers a bright breakfast and lunch menu. The Rosemary Beach Inn is a boutique inn that embodies the best of this small village. Rosemary Beach is unique because it is a newer development that embraces the small beach vibe.

These ten small towns in Florida represent the best of the Sunshine State. From historical sites like the Castillo de San Marco in St. Augustine to tropical havens like Anna Maria Island and Key West. The towns are warm and welcoming, and walking through the historic areas is like walking back in time.

Of course, there are modern amenities like the sophisticated dining at Rosemary Beach or the art scene at Vero Beach. These towns are in different parts of the state but share yesteryear's "old Florida" atmosphere.

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