Siesta Key Beach, Sarasota, Florida.

The Most Picturesque Small Towns in Florida

Florida is a hotspot destination for travelers because of the scenery and tropical atmosphere. The bigger metropolises like Miami and Orlando are well documented and receive scores of visitors every month. However, the smaller towns hold the most appeal and charm.

These are the most picturesque small towns in Florida for different reasons. Some towns are landlocked, while others resemble the Caribbean, with white sandy beaches and clear water. These ten towns embody what Florida represents to so many people.

Siesta Key

Siesta Key Beach, Sarasota, Florida.
Siesta Key Beach, Sarasota, Florida.

Siesta Key is a beautiful barrier island off of Sarasota. It's known for its pure white quartz sand and azure-colored waters. The eight-mile island is a hub for fishing, scuba diving, and parasailing. The Siesta Key Breeze Trolley is free and offers the best way to see the island, though walking is also a great option.

Siesta Key Village is the heart of the island, where you will find shops, boutiques, and eateries. Siesta Key Oyster Bar is one of the more popular restaurants and converts to a Chicago Bear-driven sports bar on Sundays. Siesta Key is consistently ranked among the best beaches in the world and is one of the most picturesque in Florida.

Cedar Key

Cedar Key Sunset with beautiful colors.
Cedar Key Sunset with beautiful colors.

Cedar Key is a barrier island in Northwest Florida known for its authentic, old Florida vibe. There are two nature refuges: Cedar Key Museum State Park and the Cedar Key National Refuge. The museum is 18 acres of preserved land with a trail leading to the salt marshes. The wildlife refuge is only accessible by boat and contains over 20,000 bird species. It provides a golden opportunity to see the unique history of the island.

The Cedar Key Fishing Pier is perfect for surf fishing and gazing at sunsets. You won't find any chain restaurants here, which adds to the charm. Popular spots like 2nd Street Cafe and Steamers Clam Bar and Grill are among the top restaurants on the island.

Mount Dora

Panoramic view of Mount Dora Lighthouse, Mount Dora, Florida, USA.
Panoramic view of Mount Dora Lighthouse, Mount Dora, Florida, USA.

Located in Central Florida, Mount Dora is a charming southern town with a fascinating history. The town centers around Lake Dora and Mount Dora Lighthouse at Grantham Park. It is also known for its bustling downtown that comes alive over the weekends.

There are also historic bed and breakfast inns, like the famous Lakeside Inn. Built in 1883, it is considered Florida's most historic bed and breakfast. The inn includes five yellow buildings and 90 rooms. The lakefront, historic buildings, and walkable downtown make Mount Dora one of the prettiest towns in Florida.

Fort Walton Beach

Fort Walton beach fishing pier.
Fort Walton Beach fishing pier.

Known locally as FWB, Fort Walton Beach is a small country town on Okaloosa Island with white sandy beaches. In addition to the striking beaches, attractions like the Gulfarium Marine Adventure Park are popular. They host classes and tours and showcase the fragile state of marine life.

Historical sites include the Indian Temple Mound Museum and the Air Force Armament Museum. The Mound showcases Northwest Florida's heritage from 14,000 B.C. through the 1950s C.E.. The Air Force Armament Museum includes exhibits and tours that celebrate the strong military history in the local area.

Panama City Beach

Panama City Beach, Florida, Russell-Fields Pier at sunset.
Panama City Beach, Florida, Russell-Fields Pier at sunset.

Panama City Beach, or PCB, is a party zone for Spring Breakers, but there is plenty to see and do year-round at this famous beach. Besides the miles of sugar sand beaches, St. Andrews State Park is a major draw. The park hosts multiple species of migratory birds throughout the year, and you will not want to leave once you gaze upon the emerald-green waters and pristine beaches.

The Panama City Beach Conservation Park includes 24 miles of hiking trails and a mile-long boardwalk. This is a great way to see Florida's natural habitat and the stunning beaches for which PCB is known. The preserves and the beaches make Panama City Beach stunning and one of the state's best beach locations.


View of 5th avenue at sunset in Naples, Florida. Editorial credit: Mihai_Andritoiu /
View of 5th Avenue at sunset in Naples, Florida. Editorial credit: Mihai_Andritoiu /

Naples is on the Southwest coast, known for its architecture, and is a world-class, sophisticated shopping destination. These shops are located on Fifth Avenue and Third Street South downtown. The shopping ends on the beach, where outdoor cafes offer breathtaking views of the blue Gulf of Mexico.

The Naples Pier was erected in 1888 and has undergone several rebuilds due to hurricanes. It is the ideal spot to watch sunsets and surf fish. And don't worry; there are plenty of beach hotels like La Playa Beach and Golf Resort where you can stay for a couple of days and complete the Naples experience.

Key West

Key West famous Duval street panoramic view, south Florida Keys, United states of America.
Key West famous Duval Street panoramic view, south Florida Keys, United States of America.

Key West, the southernmost point in the continental United States, is a beach lover's dream. Only 90 miles north of Cuba, this tiny island has a great history, including Native Americans and celebrities like Ernest Hemingway. After a day at the beach, Duval Street is party central. You will find pub crawls, costumed figures, and the famous Sloppy Joe's Tavern here.

The Hemingway Home and Museum celebrates the life of the secluded writer with original furniture, including the six-foot wall he built around his home. Walking tours are available, which are the best way to get a feel of the island and the history that shaped it. Most tours start at the Key West Cemetary, which shows off the locals' eclectic humor and Key West's history.


Idyllic turquoise bay in Islamorada on Florida Keys, Florida, USA.
Idyllic turquoise bay in Islamorada on Florida Keys, Florida, USA.

Islamorada comprises six of the Florida Keys and is known as the "sport fishing capital of the world." Watersports like boating, scuba diving, and fishing dominate the area, but there are many more attractions on land to consider. The History of Diving Museum is popular and offers exhibits and tours exploring local diving history.

The Theatre of the Sea is a fun aquarium offering tropical gardens, sea lions, dolphins, and other aquatic wonders. Robbie's of Islamorada is a family-friendly park where you can feed tarpon and see what makes Islamorada so special. It is considered the busiest attraction in the Florida Keys. Islamorada has a world-famous beach and feels like a Caribbean vacation without leaving the States.

Winter Garden

Aerial view of Winter Garden Florida, Lakeview Park.
Aerial view of Winter Garden Florida, Lakeview Park.

Winter Garden is a southern town in Central Florida. It is not unusual to be passed by a golf cart or bicyclist. The downtown area was designed for walking and leisurely activities. The town is only 20 minutes from Disney World and is a popular tourist lodging area.

This charming town was founded in 1908, and the citrus industry put it on the economic map. Historic Downtown is a perfect walking area filled with quaint shops like The Ancient Olive Gourmet and the Farmer's Market. Winter Garden is perfect for those looking for a charming and scenic getaway.

St Augustine

St. Augustine, Florida, USA Downtown Skyline Aerial.
St. Augustine, Florida, USA Downtown Skyline Aerial.

Founded in 1565, St. Augustine is the longest continuously habited European settlement in the United States. It is a virtual time portal to the 18th century, where period actors are not uncommon to be encountered on historic St. George Street. Castillo de San Marcos is an 18th-century fort with live reenactments and exhibits.

This is definitely a walking town, and St. George Street is the center of the walking attractions. Along with bed and breakfast inns, this pedestrian-only road leads past several shops and restaurants, including the St. George Tavern, a popular spot for locals and period actors. St. Augustine is full of Old European history and architecture and offers some of the best views in Florida.

Florida is a gorgeous state. The rivers, oceans, and beaches make it one of the most pleasing states to visit. There are also centuries of history, especially in St. Augustine. These ten towns are the most picturesque, though that is a tough decision.

Whether you are looking for parties, tropical beaches, or country charm, Florida has you covered. Barrier islands like Cedar Key and Siesta Key take your breath away because of the natural scenery of old Florida. Central Florida towns like Mount Dora and Winter Garden have a different aesthetic while maintaining the Florida charm. These towns are breathtaking and have a lot of natural and historic attractions.

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