Best Small Towns in Florida for a Romantic Weekend

There’s something so charming about a small beach town. Maybe it’s the laidback atmosphere, the uncrowded streets, or the picturesque views around every corner. Maybe it’s the array of quaint little shops and local restaurants. 

Ready to slow things down in a small Florida town but want to avoid the crowds?

We totally get ya. Sometimes, an off-the-beaten-path is better than the same top 10 attractions that come up on your search feed. Finding the perfect balance between excitement and relaxation can be a challenge, especially when you’re planning a trip to Florida. But don’t worry, we’ve got you covered here. From quirky art walks to peaceful nature trails, these six hidden gems in Florida offer a unique and authentic experience that you won’t find anywhere else.

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Whatever it may be, these little towns are known to be the best places to find romance. If you’re looking to enjoy relaxing ocean tides, warm white sands, and blissful sea breezes with your better half, these 6 small Florida towns are some of the most romantic places in Florida.

Ormond Beach

Resting just north of Daytona Beach and only an hour’s drive from Orlando, Ormond Beach is just as unique as it is endearing. Known for being the “birthplace of speed,” this tiny town has a rich beach racing history that started as early as 1902, over 30 years before Daytona began the thrilling sport. Although the days of racing have long been over, there are many other great things to do for entertainment.

To spend a day of adventure outdoors, start with a scenic drive through the Ormond Scenic Loop. Throughout the drive, you’ll take in Northeast Florida’s stunning scenery of historic buildings, tree tunnels, marshes, and beaches. Along the route, there are many state parks where you can stop and hike. One of the most notable is Bulow Creek Park, where you can trail through historic sugar mill ruins and see the ancient Fairchild Oak Tree.

For a day of leisure exploring the city, take a stroll along main street and check out Ormond’s many unique shops and restaurants. Enjoy fine dining and specialty cocktails in the ornamental atmosphere of Rose Villa Restaurant, a historic building selling outstanding Southern comfort food. So whether you are looking to explore nature or the city, Ormond has something fun for every couple.


Photo credit: Deposit Photos

Get a glimpse into old Florida and visit Dunedin, one of Florida’s oldest towns. The town is known for its four-mile-long beachfront and historic Scottish roots — yes, you read that right! Dunedin has a high Scottish population, which has gifted this town with many wonderful Scottish festivities and carnivals throughout the year. Spend your stay lounging on the beach or exploring the scenic parks, trails, and historic downtown area.

Caldesi and Honeymoon Island State Park are excellent places to immerse yourself in nature and romance. Take in views of the native ospreys and make a wish at the hidden shell trees. It’s a cute spot where locals hang shells on the branches containing their deepest desires. In the evening, be sure to wander through Dunedin’s restaurant scene. There you’ll find various pubs, fine dining, and seafood joints to choose from, many of which have spectacular coastline views.

St. Augustine

Founded in 1565, St. Augustine is America’s oldest city and one of the most romantic places in Florida. Although this has drawn many tourists throughout the years, the city has managed to maintain its old-world charm that visitors travel across the world to see.

During your visit, take a romantic walk along the old cobblestone streets as you admire the Spanish colonial architecture. There are many shops, museums, wineries, distilleries, and restaurants to experience downtown — all one-of-a-kind and brimming with history and Southern hospitality. Don’t forget the castles, too! Many of the castles found in St. Augustine provide tours all year round.

Once you’ve checked downtown off your itinerary, spend one of your days roaming the city’s beautiful beaches and lush parks. Jacksonville Beach is a must if you want to see the famous St. Augustine Lighthouse, featured in many films and television shows. If you and your partner love all things spooky, during the fall season, you can take ghost tours through St. Augustine’s most haunted locations and hold onto each other extra tight!

Most important tip: Florida is known for its fast-paced cities like Miami and Orlando, but small towns are a different story. Life here moves at a slower pace, and that’s part of their charm. Don’t rush through your visit, take your time to stroll on the streets, visit local shops and restaurants, and soak up the laid-back atmosphere.

Tarpon Springs

Tarpon Springs is one of the cutest small towns in Florida. With the largest percentage of Greek Americans in any U.S. city, this hidden gem feels like you’ve been transported to a quaint little town in Greece. The city is named “the sponge capital of the world” due to the Greek sponge divers who settled there in the early 1900s. So, be sure to visit The Sponge Dock, a unique shop where you’ll find a variety of fresh, natural sponges that still smell of the salt and the sea.

Rich in history and Greek culture, there are many interesting things to explore in Tarpon Springs, such as art galleries, specialty markets, antique shops, and eateries. These places are right along the scenic waterfront in old 19th-century buildings on charming brick streets. For history buffs, the Safford House Museum is a fascinating place full of old furnishings and belongings that offer a sneak peek at life in Florida over 100 years ago. From Greek festivals to great restaurants, you won’t run out of fun things to do!


Perched right along the Gulf of Mexico is Gulfport, a small coastal town known for its eclectic, progressive, and friendly atmosphere. It’s one of those places where once you’re there, you won’t want to leave! The place has a way of making you feel welcome and a part of its vibrant, small community from just one visit. You’ll also be a short drive from the scenic views and luxury stays of 30A

You can’t help but marvel at the colorful cottages, charming Airbnbs, and old brick roads at Gulfport. It feels like you’ve stepped into a time when chain stores and parking meters are non-existent. Instead, there’s free parking, free trolleys, and all sorts of unique treasures at the many independently owned and operated shops, stores, and restaurants. Downtown frequently holds events with local artists, musicians, and craftspeople, making every day a celebration! Be sure to check out the scenic Boca Ciefa Bay, where many locals go to watch the sunset. If you’re looking for a small-town feel among a charming and tropical ambiance, Gulfport is right down your alley!

St. Petersburg

ST. PETERSBURG, FLORIDA – SEPTEMBER 2: Exterior of Salvador Dali Museum in St. Petersburg, FL. The museum has one of the largest collections of the works of Salvador Dali in the world. Photo Credit: Yayimages

St. Petersburg is the place to go if you love easy access to white-sand beaches and a flourishing art scene. The small city is hip, welcoming, and abundant in world-class museums and art galleries like the acclaimed Dali Museum and Chihuly Collections. There are plenty of art walks and festivals throughout the year as well. Take in picturesque sights of colorful neighborhoods like Grand Central District, St. Pete Pier, and Central Ave., and wander through the indie shops, cafes, and art galleries. 

For nature lovers, there is much to explore at St. Pete’s remarkable nature preserves. You and your better half could easily spend a day or two touring the many waterfront park systems, pristine beaches, and gator-sighting hotspots. Compared to big cities like Tampa, St. Pete offers a more wholesome and secluded getaway experience with lots of great opportunities for romance.

Boardwalk on the beach in St. Pete, Florida, USA Photo Credit: YayImages

Must have item on your small town vacation in Florida

If your small-town vacation includes some beach time, make sure to pack all the necessary beach gear. This could include a beach towel, swimsuit, flip-flops, and any other personal items you may need. And don’t forget to bring a good book or some music for some relaxation on the sand!

Sunhat, flip flops, towel, sunglasses, sunscreen and beach bag neatly laid out on a sandy tropical beach.
Photo Credit: Deposit Photos


What are the most affordable places to visit in Florida?

The top 5 most affordable areas in Florida are Cape Coral, Dunedin, Forst Walton Beach, Lakeland, and Vero Beach.

Which side of Florida is better for vacation?

The side of Florida that is better for you really depends on what you expect to get out of your vacation. For instance, the Atlantic coast gets better waves, which is ideal for those interested in water sports. On the other hand, the Gulf Coast is known for its white sand beaches and crystal-clear waters.

What is the cheapest city in Florida to fly into?

There are several affordable airports to consider when flying into Florida for a visit. Here are some of the cheapest:

– Fort Lauderdale-Hollywood International Airport
– Tampa International Airport
– West Palm Beach International Airport
– Orlando International Airport
– Miami International Airport

It’s the Little Things That Count

When it comes to Florida weekend getaways for couples, smaller can oftentimes be better! You can find so much charm, romance, and magic in older, smaller places. Each of these quaint, tropical towns holds such fascinating history, transporting us back in time and igniting our imagination and sense of wonder. 

So, the next time you and your true love want to go someplace special, consider one of these delightful small Florida towns. They’re what makes the Sunshine State that much sunnier.

More Romantic Florida Getaways

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