Visit These 12 Incredible Charming Small Towns in Florida, One for Each Month of the Year

Where is your favorite place in Florida for a weekend getaway? When you live in or are visiting this top vacation state, can you even narrow it down to one destination? We all know that planning the perfect escape can be challenging, especially with our busy schedules. Have no worries, let us take some of the burdens of vacation planning away from you. 

We’ve compiled a list of the 12 most charming small towns in Florida, one for each month of the year. Some of these seaside escapes are my personal favorites, and I have visited them more than I can count. While you don't need to tackle all of these to find true enjoyment in the year, it might be fun to plan for some and check these Florida vacation destinations off your bucket list!

January: Crystal River

Crystal River, Florida, in January, is one of the best ways to see the annual manatee migration. Thousands of manatees trek to this river every winter to escape the hard, cold water elsewhere. Plan a trip here in January, book a cozy vacation rental, and enjoy swimming side-by-side with these gentle giants.

February: Plant City

Plant City, Florida, is a charming town outside of Orlando that is also heralded as the Winter Strawberry Capital of the World. Come in February for the Winter Strawberry Festival and enjoy some of the finest shortcakes, pies, cobblers, and more made with the freshest strawberries in the country. Best of all? You can make your own strawberry shortcake, which is my favorite part of the festival. While you're here, enjoy a night away at this adorable bungalow located just one mile from the historic town. And if you're a train lover or have the little ones with you, the Robert W. Willaford Railroad Museum is a must-visit.

March: Dunedin

Tucked away on the Gulf Coast, Dunedin is one of the most historic towns in Florida. Here, time seems to slow down- people relax on the waterfront stretch, enjoy cruising the St. Joseph Sound, adventure out through the nearby mangroves, and spend the night at the Fenway Hotel. Plus, visit Hammock Park, offering scenic boardwalk trails, and it is home to owls, butterflies, and woodpeckers! If you want a true laid-back vacation in Florida, this town is it.

April: Sebring

There is no better place for soda lovers in April than the Sebring Soda Festival. This annual event takes place in the historic Downtown Sebring area and features over 200 craft sodas to sample. Not to mention the live entertainment, games, and the yummy food trucks. This festival is a great reason to visit this family-friendly town, and while you're here, you'll realize how tight-knit the community is. Make sure you plan plenty of time to explore afterward and book a stay at the Inn On The Lakes.

May: Fort Walton Beach

Nestled in the Florida Panhandle is Fort Walton Beach, a small town known for its sugary white sand and tons of natural beauty. This area is great to visit in May, mainly because you can kick off the summer season with visits to the picture-perfect beaches, beautiful parks, and museums, and even spend the night in a bungalow. Since it's only 10 miles from Destin, you'll have access to all the attractions while avoiding the huge crowds when you want to have a peaceful beach day.

June: Islamorada

There’s no better time to take a cruise down to Islamorada, Florida, than at the start of the summer. Encompassing six of the Florida Keys, Islamorada is known for coral reefs and snorkeling excursions. Visit the History of Diving Museum, complete with a 16th-century treasure chest, or the former quarry known as Windley Key Fossil Reef Geological State Park. There is always something to do here that highlights the beauty of the outdoors. If you ask me, this is one of the best towns to visit in Florida.

July: Micanopy

As far as history goes, Micanopy, Florida, has a lot to offer. At 200 years old, Micanopy is the oldest inland town in the state, and it is filled with antique shops, cafes, boutiques, art galleries, vacation retreats, and so much more. There is scenery in abundance, but also the charm of one of the most historic towns in Florida really draws people in. Beyond the town, Micanopy is known for its population of wild bison and wild horses at Paynes Prairie Preserve State Park. You'll want to carve out time to see these creatures in the open prairie. It's truly a one-of-a-kind experience in Florida.

August: New Smyrna Beach

Surf’s up this August when you take a trip to New Smyrna Beach! As the quintessential beach and surfing town, you’ll be able to end the summer in the best way possible. Take a stroll down Canal Street and peruse the shops. Then venture Downtown to grab tacos before hitting the shoreline for a surf session. I like the fact that New Smyrna Beach is so low-key and not as crowded as other nearby beaches. It's one of my go-to destinations in Florida to wrap up a fun summer season.

September: Jupiter

Take a trip to Jupiter, Florida, one of our top destinations for Florida vacations, for a September to remember. Home to one of the last historic lighthouses that is still in use and open to the public, this gem was built in the 1860s and is a coveted attraction in town. But beyond the lighthouse's preserved pioneer-era homestead history, Jupiter also offers beachside beauty, luxurious accommodations, and much more. Pro Tip: If you want to visit Singer Island or West Palm Beach, you'll be within 20 miles of them while avoiding the high hotel costs.

October: Dunnellon

While other states are bracing for cold autumn temperatures, we’re heading to Dunnellon, west of Ocala, for some water fun. Dunnellon has a little something for everyone, including the stunning Rainbow Springs State Park. Here, you can hike, paddle, tub, swim, and more. Cast a line and fish for an afternoon before enjoying the Dunnellon old Florida charm. You can also stay close to the river at the Rainbow River Estate on Blue Run.

November: Seaside

As we wrap up the year of travel, there is one word on our mind: relaxation. And what better way to relax than in sun-bleached sand and lapping surf? Seaside, Florida, is a small resort community on the Gulf that offers coastal magic. Dubbed one of the most charming small towns in America, you won’t ever want to leave this picturesque place. And if you're a foodie, you're in for a treat! Airstream Row, the local food truck hall with vintage trailers, is charming and offers a sea of mouthwatering cuisine.

December: DeLand

We’re ending the year with a bang by visiting one of our favorite destinations in Florida: Deland. This small town comes alive during the wintertime, whether it’s from the decorated streets or the nearby Stetson Mansion holiday tours! While you might not get a lot of snow here, you’ll still be able to enjoy the small-town holiday charm. If you need accommodations, make a reservation at the Hontoon Landing Resort & Marina.

What do you think about these charming small towns in Florida? Have you visited any already? Are you excited to add some to your list? Or, if you have some of your own favorite small towns to share across the Sunshine State, tell us which ones through our nomination page!

Meanwhile, when you’re planning all of your monthly excursions, make sure to check out these top hikes in Florida to see what you can include in your itinerary! Even better? Personalize your own adventure by using Only In Your State’s itinerary planner. Your next vacation is only a few clicks away!