Waterfront view in St. Augustine, Florida

13 Picture-Perfect Towns in Florida

Florida is one of the prettiest states in the US and is one of the most visited. And it is not just because of that famous Mouse in Orlando. Florida offers visitors natural scenery from white sand beaches to virtually endless forests and wetlands. 

Some of the best spots to visit are small towns that hold onto the Old Florida charm and character that once defined the state. Although the heavily visited metropolises have a lot to offer travelers, the small towns in Florida embody a certain type of atmosphere that makes people want to stay. Here are 13 picture-perfect towns in Florida that are away from the beaten path that makes for a perfect road trip.

St. Augustine

Shops and inns line St. George. Once the main street, it is still considered the heart of St. Augustine, Florida
Shops and inns line St. George. Once the main street, it is still considered the heart of St. Augustine, Florida, via Sean Pavone / Shutterstock.com

No trip to Florida is complete without stopping at St. Augustine. What makes St. Augustine picture-perfect is its Spanish architecture, cobblestone streets, and the sense that one is walking back in time. The oldest town in the US, St. Augustine is full of historical buildings and monuments that are open to the public to enjoy.

The most popular historic building in St. Augustine is the Castillo de San Marco, the fort that once protected the town. Historic St. George Street has an abundance of historical sites including the oldest schoolhouse in the US, Ponce De Leon's Fountain of Youth, and the country's oldest jail. There are also modern shops and restaurants, along with quaint inns and historic hotels. The best way to get around is on foot so visitors can take their time and soak in all this town has to offer.  

Key West

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

Key West is the southernmost point in the US and the crystal clear water and white sand beaches bring in droves of visitors every year. The small island is known for the coral reefs just offshore and is a mecca for sport fishing and scuba diving. Key West also boasts a roaring nightlife that culminates in the annual Fantasy Fest extravaganza, held every October. 

The Hemingway House, once home to Ernest Hemingway, is the most popular historic home on the island and daily tours are available at the property. His favorite haunt, Sloppy Joes, is arguably the most popular bar in town to grab a cold one. Other historic attractions include the Key West Lighthouse, the Truman Little White House, and the Fort Zachery Historic State Park. Key West is a funky little town that knows how to party while at the same time embracing its cultural history.

Islamorada

Visitors feeding fishes and pelicans in Islamorada, Florida.
Visitors feeding fishes and pelicans in Islamorada, Florida.

Islamorada is another beach town on the Florida Keys archipelago and is known as the sport fishing capital of the world. It encompasses six of the Keys and has a spectacular coral reef system that attracts scuba divers from around the world. The History of Diving Museum is a homage to the rich diving history that offers a chronological look at the history of diving. Along the same lines, The Theatre of The Sea is a marine mammal park where visitors can swim with bottlenose dolphins and sting rays.

The island's natural beauty is stunning and it is best to experience it on foot or a rented bicycle. The Keys History and Discovery Center is an excellent spot to start your journey because once you learn a bit about the history of the archipelago, it becomes more magical. 

Panama City Beach

Pier Park is Panama City Beach's premier shopping and entertainment destination located across the beach.
Pier Park is Panama City Beach's premier shopping and entertainment destination located across the beach. Editorial credit: Fotoluminate LLC / Shutterstock.com

Panama City Beach, or PCB for short, is a vacation and spring break destination in Florida's panhandle. The reason for its popularity is because of the miles of sugar sand beaches and the clear water of the Gulf of Mexico. There are also two nature preserves, each with plenty of hiking trails and several state parks.

St. Andrews State Park is a 1,200-acre nature preserve that is just east of the beach with over one mile of protected beachfront, dunes, and a pine forest. The best way to view PCB, for the brave, is by riding on the Skywheel. It's an all-around entertainment venue but the famous Skywheel is a 187 feet high observation tower with 30 gondolas. PCB is one of the prettiest towns in Florida and has plenty of venues and natural landmarks to discover.

Sarasota

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

Sarasota, on the southwest coast, is a beautiful town with many cultural centers and miles of sugar sand beaches. One of the more popular cultural centers is the Ringling Museum of Art, which showcases classic and modern art. If the Ringling name sounds familiar, it's because Sarasota was once the winter home for the Ringling Brothers Circus, a great source of pride for the locals. 

Two of the prettiest beaches are Lido Key and Siesta Key. Siesta Key is a wedding venue destination for many because of its isolated beaches and copious mangrove forests. If you find yourself on Siesta Key on a Sunday, make sure to check out the drum circle, a weekly session held on the beach from 5:00 PM-10 PM.

Naples

The beautiful downtown area of Naples, Florida
The beautiful downtown area of Naples, Florida

Naples is an hour south of Sarasota and is an affluent community with year-round sunny weather and gorgeous beaches. The town was named after the town in Italy, and the bulk of the architecture reflects the Italian style. The symbol of the town is the pier, which was erected in 1888, and is a prime spot for sundowners or for watching dolphins.

This is a popular retirement area because of the high-end shopping, dining, and golf courses. The sophisticated downtown is divided into four regions, each with its unique flair and distinctive shops and restaurants. 5th Avenue South is the de facto main street and it stretches from Tamiami Trail to the beach and is also home to the bulk of the bustling nightlife.

Micanopy

Historic downtown Micanopy, near Gainesville, Florida.
Historic downtown Micanopy, near Gainesville, Florida.

Micanopy is a quaint town in the center of the state and is the antique capital of Florida, which is a major draw for visitors. Named for Seminole Chief Micanopy (ca.1780-1849), this once bustling commerce hub is now lovingly known as "the town that time forgot". The town only covers 1 square mile, but the classic brick aesthetic that borders the willow tree-canopied roads is like walking back in time.

Like many Florida towns, Micanopy has a unique history, but this town has bottled up the nostalgia and centered itself around it. Make sure to stop in at the Micanopy Historical Society Museum to discover the past that defines this southern town. Cholokoka Boulevard is the heart of Micanopy and, if you are a nature lover, the Tuscawilla Preserve, a 600-acre nature preserve is only a mile off. Micanopy is a throwback to days of old and it introduces visitors to the Old Florida way of life like perhaps no other town in the state.

Mount Dora

Downtown Mount Dora in Florida
Downtown Mount Dora in Florida, via Nigel Jarvis / Shutterstock.com

Mount Dora is a historic town in central Florida that is known for its southern charm and hospitality. It has a quaint downtown overlooking Lake Dora that is home to numerous antique shops. The lake also has one out of only three freshwater lighthouses in Florida.

Along with numerous museums, Mount Dora also has several parks which add to its charm and aesthetic appeal. The Annie Donnelly Park, located near downtown, is where the annual tree lighting takes place and is surrounded by centuries-old willow trees. Much like Micanopy, this town is a throwback to a simpler time in life and wholly embraces its cultural roots. 

Fernandina Beach

Downtown Fernandina Beach, Florida.
Downtown Fernandina Beach, Florida. Editorial credit: JohnHancockPhoto / Shutterstock.com

Fernandina Beach, on Amelia Island, is a small fishing community with one of the most unique downtown areas in Florida. The French, Spanish, and English have all had a hand in this historic town's foundation, and elements of each culture can still be found here in the architecture, foliage, and cultural heritage. 

The pedestrian-friendly downtown is part of the National Main Street Program and encompasses 50 blocks of green canopied streets, cobblestone sidewalks, and historical buildings. Historic Centre Street is the focal piece and it stretches for eight blocks, winding around Victorian-era buildings that host numerous shops and restaurants. The harbor is never far off and this is an idyllic place to visit for its natural beauty, coastal charm, and historic landmarks. 

Palm Beach

Scenery of the shopping street in West Palm Beach, Florida.
Scenery of the shopping street in West Palm Beach, Florida.

Palm Beach is an island that is separated from the mainland by the Lake Worth Lagoon on the southeast coast. It is defined by its luxurious real estate, including the famed resort, Mar-A-Lago, and the long stretch of beach, Palm Beach Municipal. The world-famous Worth Avenue offers high-end shopping and restaurants that draw guests from around the world. 

The Henry Morrison Flagler Museum is here and visitors can tour the real estate and railroad tycoons mansion. This is a beautiful town to explore on foot, with Worth Avenue being the centerpiece. The palm-lined streets that dead end unto the beach are opulent and home to some of South Florida's most luxurious homes.

Crescent City

Aerial view of Crescent City, Florida
Aerial view of Crescent City, Florida, via Pipas Imagery / Shutterstock.com

Crescent City is located in the middle of the state along the shores of Crescent Lake and is largely regarded as the "bass capital" of Florida. The lake is the centerpiece of the town and the mixture of suburban and rural architecture adds to the appeal. The historic downtown is registered on the National Registry and the Hubbard House, which was built in 1880, is open to visitors.

The historic downtown is also home to the world-famous Three Bananas restaurant and guided walking tours are available. Most of the homes were built around the turn of the 20th century and the rural area is a time portal to a different time. Along with the historic homes, there are historic bed and breakfast inns available, including the Sprague House, built in 1892. Crescent City is off of the beaten path, and that designation makes this town a true destination.

Apalachicola

View of Apalachicola, Florida, from a bridge over the river.
View of Apalachicola, Florida, from a bridge over the river.

Apalachicola, in Florida's panhandle region, is the center of the state's "Forgotten Coast". The small town was once Florida's third busiest port and today is known for its prime oysters, shrimp, and blue crabs. The historic downtown area boasts over 900 homes and buildings dating from the 1830s and daily walking tours are available. Part of the history is that the downtown area was intentionally built into six squares in the 19th and early 20th centuries built around Washington Square.

Downtown Apalachicola sits on the bay and the majority of the buildings are classic brick architecture. The port town has a rich maritime history which is showcased at the Apalachicola Maritime Museum. Apalachicola is a gorgeous town drenched in history that has converted into a town for creatives as evidenced by the commercial buildings that now house antique shops and art galleries.

Englewood

Pier in Englewood, Florida
Pier in Englewood, Florida

Englewood is a former commercial fishing village on the southwest coast between Fort Myers and Sarasota. The uncrowded beach is the main attraction and Blind Pass Park is ideal for sea shell and shark tooth hunting. Along with the beach, Englewood has plenty to offer nature lovers including Indian Mound Park, a string of nature trails that crisscross a 2,600-year garbage disposal area.

There is plenty of shopping in Englewood too starting at Dearborn Street, the de facto center of town. The best way to experience Englewood is by renting a bicycle or walking. The historic town has several nooks and crannies that can be easily missed in a car. 

A lot of people think of the beach when they think of Florida, and for good reason. However, if you take the path less traveled, Florida offers a different glimpse of what makes the state so unique. From historic homes to ancient garbage dumps, these 13 towns will transport you back in time to a simpler time while still offering modern amenities. 

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