Large groups of visitors and tourists explore the array of shops near the end of Saint George street in Saint Augustine, Florida on an early January afternoon.

11 Small Towns in Florida to Visit for a Weekend Getaway

Florida is a perfect location for a weekend getaway. The historically significant state has something for everyone, from world reknowned beaches, islands, unspoiled nature preserves, and of course, a world famous mouse at the center of it all. However, if you are looking for a remote weekend away from the crowds, there are small towns that hold their own in terms of activities and history. 

Saint Augustine

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

When discussing idyllic small Florida towns, no list is complete without mentioning St. Augustine. As the nation's oldest incorporated town, the town is replete with history and unique attractions. The heart of the historic district is St. George Street and this is the central focal point of must-see historical sites.

Castillo de San Marcos in St Augustine, Florida
Castillo de San Marcos in St Augustine, Florida

Among the famous sites are the country's oldest schoolhouse, the oldest jail, and the Fountain of Youth. Though the town is perfect for a weekend getaway, it takes multiple trips to experience all that St. Augustine has to offer. The best way to absorb all you can on a weekend is to plan out the trip ahead of time. To really get the feel of the town, staying in a historic bed and breakfast like the St. Francis Inn is the way to go. 


Aerial view of Islamorada, Florida
Aerial view of Islamorada, Florida

The small village of Islamorada encompasses six of the Florida Keys and is a world-class sport fishing destination. Islamorada has the best coral reefs and shipwrecks in the US, and is a scuba diver's paradise. There is also ample snorkeling, paddleboarding, and kayaking.

On land there are attractions like the Theatre of the Sea and a unique diving museum that elaborates on the connection of underwater exploration and the beautiful village. If you want to add luxury to your weekend, staying at the Cheeca is the best bet. This luxurious beachfront hotel and spa offers rooms, suites, and villas along with a fine dining restaurant, La Casita. 

Anna Maria Island

Drone view of Bean Point Beach on Anna Maria Island
Drone view of Bean Point Beach on Anna Maria Island. Editorial credit: Noah Densmore /

Anna Maria Island is a barrier island on Florida's west coast and is best known for its jaw-dropping beaches. Inland is a resort town with upscale shopping and historical buildings. The Anna Maria Island Historical Society Museum includes a cottage built in 1920. A wooden pier built in 1911 is only a stone's throw away and is a reminder of the continuity of the past blending with the present-day shops and boutiques. 

The best time to visit is between January and March, when the weather is cooler and there are less tourists. Though all of the lodging options are a popular choice, the Anna Maria Island Inn is a no-fuss, quaint yet luxurious hotel that is highly recommended. 

Mount Dora

Colorful Mount Dora's downtown area, a popular tourist destination
Colorful Mount Dora's downtown area, a popular tourist destination, via Jillian Cain Photography /

Mount Dora is a quaint town in central Florida known for its antique shops and annual festivals. The town centers around Lake Dora, complete with a lighthouse surrounded by picnic tables. Along with the historic homes, the Mount Dora History Museum is in a 1923 firehouse and the Museum of Speed is inside a 1940's gas station.

This is a fun town to visit for a weekend. Perhaps it's the fact that it is not mainstream Florida like the bigger metropolis' and it offers a different view of Florida that some may not know exists. Staying at the Lakeside Inn, Florida's oldest hotel, completes the historic experience. Staying here is like traveling back in time and exudes the charm of Mount Dora like no other hotel does. 

Captiva Island

Stunning aerial view during sunrise of Captiva Island and Sanibel Island.
Stunning aerial view during sunrise of Captiva Island and Sanibel Island. Editorial credit: Noah Densmore /

Captiva Island is a charming island just west of Fort Myers and is generally considered with its neighboring island, Sanibel. Traveling over the causeway to get to the island is a firsthand experience in authentic Florida. The two and a half miles of pristine beaches are covered in seashells and the beach is considered the seashell capital of the US.

Captiva hangs on to its small beach community feel by not allowing any commercial buildings to be taller than the tallest tree on the island. This way, visitors and locals can revel in the natural beauty of this unique place. The South Seas Resort is new and is getting high reviews because of their private beaches and amenities. 

Winter Park

In and around Kraft Gardens in Winter Park, Florida.
In and around Kraft Gardens in Winter Park, Florida.

Winter Park is in the center of the state and, much like Mount Dora, gives visitors a unique look at another side of Florida. The small town is set against Lake Osceola, renowned for its premier bass fishing, and boasts a number of museums. The Charles Hosmer Morse Museum of American Art has a Tiffany Collection while the Albin Polasek Museum & Sculpture Gardens showcases works by eponymous artists. 

The pleasant downtown includes cobblestone streets along with shops and boutiques set in vintage and antique brick buildings. The open nature areas and majestic trees accentuate the affluence of Winter Park. The Alfond Inn is an exquisite hotel that is convenient to the restaurants and shops of downtown and offers luxury amenities, including a conservatory. 

Palm Beach

Aerial view of Palm Beach in Florida
Aerial view of Palm Beach in Florida

Palm Beach is an island on the East Coast of Florida and home to mansions, historic landmarks, and museums. One of the more famous residents was Henry Flagler and there is a museum dedicated to him here. The atmosphere here is pure south Florida, replete with colorful buildings and luxurious shopping on the famous Worth Avenue. 

While shopping is among the main draws in Palm Beach, one cannot forget the Caribbean-tinged beach.Clematis Street hosts some of the best nightlife in the area and is conveniently located in between the beach and Lake Worth. The pink Colony Hotel, rated four stars, offers the true atmosphere and kitschness of Palm Beach and is a perfect weekend getaway. 


Aerial view of Stuart, Florida
Aerial view of Stuart, Florida, via Noah Densmore /

The Atlantic Coast town of Stuart, known as the "Sailfish Capital of the World" is a quaint town rich in history. In fact, the  House of Refuge at Gilbert's Bar was once a safe haven for shipwrecked sailors and is a popular visitor attraction. The Stuart Heritage Museum contains historical pieces and furniture from the original pioneers.

Along with the picturesque streets and history, Stuart also boasts amazing outdoor activities. The Seabranch Preserve State Park has hiking and nature trails and the offshore fishing is top notch. The Old Colorado Inn is a historic boutique hotel in the heart of downtown, which saves driving time for a short weekend getaway. 


Aerial view of Naples, Florida.
Aerial view of Naples, Florida.

Naples is a luxurious community in southwest Florida. The town's symbol is the wooden pier, built in 1888 but modern Naples is known for its high end shopping and golfing. It is the perfect mix of sophisticated living and classic Florida outdoor attractions like deep sea fishing and kayaking.

The sugar sand beaches are perfect for sunset viewing, and with 230 days of summer annually, there is no bad time to soak in the sun. However, October-March are highly populated because the "snowbirds" flock here from the colder, northern temperatures. There is almost no limit on lodging but La Playa Beachfront Resort and Golf Club exemplifies the best that Naples has to offer. 

Weeki Wachee

Weeki Wachee, Riverside Restaurant
Weeki Wachee, Riverside Restaurant. Image credit Linda White Wolf via Shutterstock

Weeki Wachee, with a population of eight, is a family friendly adventure. The Weeki Wachee State Park is the biggest draw and here is where you find live mermaids, glass bottom boats, and natural springs. There are river boat cruises or you can take a swim in Buccaneer Bay.

Built in 1947 as a way to teach people about Florida, the State Park hosts several annual events including classic car shows and Breakfast with Santa. Neptune's Grotto is a fun retreat in Weeki Wachee with uniquely themed rooms that will round out your adventurous weekend. 

Pompano Beach

Pompano Beach, Atlantic Ocean coast looking north toward the Hillsboro Inlet Lighthouse
Pompano Beach, Atlantic Ocean coast looking north toward the Hillsboro Inlet Lighthouse. Image credit Serenethos via Shutterstock.

Pompano Beach is a small town north of Fort Lauderdale on the Atlantic Coast. It attracts a lot of scuba divers because of the coral reef, multiple diving sites, and the beaches. On shore, there is excellent dining, an antique mall, and even a Harrah's Hotel and Casino

The beach town is a cultural arts hub, and unique exhibits are on display at the Ali Cultural Arts Building and the Bailey Contemporary Arts building. The Festival Marketplace is a quarter mile long shopping district with over 250 kiosks and boutiques,  along with restaurants. The town is also convenient to get to, with the Fort Lauderdale Hollywood International Airport only eight miles south of the beach. 

Florida is home to quirky attractions, history, and pristine beaches. Whether you are looking for fun family adventures in Weeki Wachee or more grown up fun Harrah's, Florida has it all. And, although the beaches are well written about, if you spend a weekend inland of the beaches, you will discover true Florida gems like Mount Dora and Winter Park, offering a glimpse of a different side of Florida. 

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