10 Beautiful Towns In Florida Worth Visiting For A Weekend Getaway

Florida is often associated with theme parks and large, touristy resorts, but the Sunshine State also has a quieter, beautifully scenic side that's perfect for short escapes. Away from the crowds and pricey Walt Disney World Resort, Universal Orlando Resort, and can't-miss tourist attractions, Florida is home to a vast array of charming beach towns, historic cities, and communities that still feel like Old Florida never left. These are the types of destinations that make for perfect weekend getaways. Whether you're coming from out of state to escape the winter doldrums or you're a Florida resident looking to experience a new town, this coastal state was made for weekend travels.

Travelers who live in Florida or visit frequently can spend one weekend strolling cobblestone streets in the nation's oldest city and the next eating some of the best seafood in the world. In this guide, we'll explore 10 beautiful towns in Florida that are worth visiting for weekend getaways. Each destination offers its own distinct vibe, whether it's stunning scenery, historic landmarks, or upscale culture. These Florida towns are proof that the best trips are sometimes the most unexpected.

Known for its gorgeous white sand, distinctive coastal dune lakes, and effortlessly cool atmosphere — the town's unofficial tagline is "nice dogs, strange people" — Grayton Beach is the perfect mix of natural beauty and artistic spirit. Situated near Highway 30A, Grayton Beach feels unpolished in the best way. This is in sharp contrast to nearby towns like upscale Seaside and Rosemary Beach, where people often go to see and be seen. Here, people can truly slow down for the weekend while enjoying a slow pace and great local activities. The ruggedly beautiful Grayton Beach State Park is a major draw, offering hiking and cycling paths that range from one mile to four-and-a-half miles, snorkeling, kayaking, and paddleboarding. Camping is also popular at the park, but travelers need to plan well in advance to actually secure a site at this sought-after location!

Divers can enjoy one of the most unique experiences in the world here: a visit to the Underwater Museum of Art, which is located 58 feet under the surface of the ocean. It features a collection of waterproof sculptures from global artisans. Food is also a big player for those who decide to spend a weekend in Grayton Beach. Multiple standout local restaurants and bars reflect the town's eclectic personality. Red Bar is, perhaps, the most well-known establishment here. Famous for its funky live music, maximalist interior, and devil-may-care attitude, Red Bar was reopened in 2020 following a terrible fire, and never once lost its mojo throughout its year-and-a-half closure. Chiringo is another excellent spot, right on the beach. This is one of my personal favorite beach bars anywhere in the world — make sure you order the tuna poke bowl for lunch!

Apalachicola is a historic fishing, timber, and railroad town on Florida's Forgotten Coast, known for its beautifully preserved architecture, quiet streets, and passion for history. Arriving in this tiny town of 2,300 feels like stepping back in time, with brick buildings lining its single main road and a languid pace of everyday life. One of the main reasons to visit Apalachicola is its amazing seafood scene. The town is particularly famed for the oysters harvested from Apalachicola Bay. Restaurants like The Station Raw Bar, Half Shell Dockside, and Lynn's Quality Oysters celebrate this heritage with their menus every day. Visitors and locals alike can also enjoy annual events like the Apalachicola Oyster Cook-Off and the Florida Seafood Festival.

In addition to being a world-class destination for seafood foodies, Apalachicola is the perfect weekend escape for history lovers. Boasting an astounding 250 buildings on the National Register of Historic Places, there's no shortage of beautifully preserved sites to explore here. The Coombs Inn & Suites, a converted 1905 residence that now serves as a popular bed and breakfast, is a wonderful place to stay for a weekend in Apalachicola. Shopping in the historic downtown district is a great way to while away an afternoon. Make sure to check out The Shop, a popular spot with a mix of home goods and local treasures, Grady Market for high-quality clothing and gifts for everyone on your list, and Inspired Too to browse a range of handmade items, from soaps to jewelry to housewares.

St. Augustine is one of the most distinctive weekend escapes in all of America, not just Florida. Established in 1565, the town's claim to fame is that it is the oldest continuously inhabited European-founded city in the United States. This underrated city is a historic gem with coastal charm, brick and cobblestone streets, Spanish colonial architecture, and landmarks that have stood for centuries. St. Augustine presents more like a picturesque European village than a Florida beach town, which makes it wildly appealing for those who want a Euro-centric getaway but don't have the money to fork over for even one of the more affordable European destinations. Aviles Street, the oldest street in the country, is a great place to start any stay here. This road is known for art galleries like the Ancient City Gallery and Jensen Pottery, and museums including the Spanish Military Hospital Museum — a recreation of an 18th-century setup, complete with period performers.

Weekend travelers should consider arriving on the first Friday afternoon of the month to take part in Aviles Street's First Friday Art Walk, an event that allows people to peruse galleries after hours while snacking on small bites and enjoying drinks. For history buffs, Castillo de San Marcos is a must-visit. This 450-year-old fort is now a National Park site, and a tour will expose centuries of Spanish rule, British occupation, and even pirate lore. Consider staying at the Hilton St. Augustine Historic Bayfront, near Castillo de San Marcos and the famed Bridge of Lions, or the Casa Monica Resort & Spa, which is housed in a historic structure from 1888. For dining, New Orleans-inspired Harry's Seafood Bar & Grille is always a great choice here. Caps on the Water is another excellent option, particularly for those who want a spectacular sunset view during dinner.

Located on Amelia Island just off Florida's Atlantic coast, Fernandina Beach is known for its well-preserved Victorian architecture; the town's historic downtown feels like a postcard of Florida at the turn of the 20th century. Wandering the brick streets, weekend visitors can enjoy photographing grand homes like the 1885 Queen Anne style "Bailey House" and the "Lesesne House," which was constructed in the Classic Revival style in 1860. The walkable downtown area also boasts a variety of locally-owned shops, bars, and restaurants. For drinks, highlights include the Palace Saloon, the oldest operational bar in the state, and The Decantery, where craft beer, wine, and cocktails are available all day. David's Restaurant is a great option for a high-end date night meal, while shoppers will enjoy specialty retailers like Amelia Fine Jewelry and the Book Loft.

Fernandina Beach is also known for its 13 miles of lovely beaches, where weekend revelers can enjoy a full day of fun. The park near the town's main beach is dog-friendly and offers multiple activities like volleyball and playgrounds for kids. Just a few minutes away by car, families can enjoy local favorite Tasty's Best Burgers. Fernandina Beach is a pretty town perfectly suited for a weekend getaway for both couples and families with little ones. Two or three days is plenty of time to explore the historic district, enjoy delicious meals, and spend time by the water before heading home. The historic Florida House Hotel is a great home base for a short getaway here. The town's understated elegance and beachy charm make Fernandina Beach one of Florida's loveliest weekend escapes.

Long before The Walt Disney Company ventured into multi-million dollar real estate with its Golden Oak development, there was Celebration. Designed by Disney in the 1990s, locals often describe this picturesque community as "the bubble," and it's easy to see why living here — or just visiting for the weekend — feels like an escape from real life. This master-planned town was engineered from day one with an overarching emphasis on walkability, charm, and visual appeal. This is one of those charming, retro towns that feels stuck in time in the best way possible. Retro-inspired buildings, including a movie theater and a post office that look straight out of the 1950s, and neighborhood-oriented spaces like swimming pools and tennis courts, create an instant storybook quality here. Popular restaurants include the lovely Le Macaron French bakery and Columbia Restaurant, a quietly elegant wood-paneled space that has been serving diners since 1905.

Although Disney has not officially owned Celebration since 2004, the town of about 13,200 still has some magical details, like gates featuring Mickey ear motifs on some residences! And, true to form, the attention to detail here is typical of The Walt Disney Company. Many homes and commercial structures in Celebration were inspired by Walt's own era, spanning from the turn of the 20th century through the 1940s and 50s. If you plan to enjoy a weekend here, the gorgeous Inn at Celebration is the town's premier place to stay. With coastal glam interiors and onsite dining at the Lakeside Kitchen & Bar, guests can have an exceptional experience without even leaving the hotel property. Celebration effortlessly hits the mark every time.

Most people don't imagine scenic hills and farmland when they think of Florida, but that's exactly what Mount Dora delivers. Far different from the flat, beachy version of the state many travelers expect, this town makes for an exceptional weekend getaway. Mount Dora is especially known for its numerous antique shops, like Renninger's, and dozens of annual festivals. The town is home to only around 12,500 residents, yet it hosts upwards of 30 festivals every year, so no matter which weekend you visit, there's likely to be an event going on. The Mount Dora Arts Festival, which has existed for more than 50 years, is one of the town's most popular annual events. Sometimes festivals even overlap, with the same February dates, for instance, playing host to the African American History Festival and the Jane Austen Festival. There's truly something for everyone here from a festival standpoint.

Mount Dora is also popular among outdoor enthusiasts, thanks in large part to its lakeside setting and biking terrain. And, yes, before you ask, there is, of course, an annual Bicycle Festival here. Boat tours on Lake Dora and the Dora Canal are a great way for weekend visitors to enjoy local scenery and spot wildlife. For dining, The Yardery — a colorful spot inspired by popular childhood pastimes — and the scenic Lake Eustis Waterfront Grille are both excellent options for the whole family. For visitors looking for something a bit more romantic, Lakeside Inn's Beauclaire Dining Room offers an upscale experience. The hotel itself, which opened in 1883 and has been operating longer than any other accommodations in Florida, is also a lovely place to stay.

Sarasota is one of Florida's most beautiful and elegant destinations, known for its fantastic arts and culture, as well as gorgeous scenery. In addition to being a great place for a weekend getaway, this refinement has made Sarasota one of the nation's most favored retirement destinations. Art museums and performing arts venues give Sarasota a feeling of sophistication that sets it apart from the majority of Florida's more casual beach towns. The Ringling Museum is a highlight for weekend vacationers. This one-time estate of John and Mable, of the circus Ringlings, is comprised of five distinct sections, each more fascinating and beautiful than the last: the world-class Museum of Art, the colorful and quirky Circus Museum, the Italian-inspired Ca' D'Zan mansion, the 18th-century Historic Asolo Theater that was transported from Italy in 1949, and the Bayfront Gardens.

For many culture enthusiasts, the Sarasota Opera is the standout performing arts troupe in the city. For over a century, the opera has been performing classics like "La Bohème" and "The Merry Widow." The Sarasota Ballet is another artistic cornerstone here, delighting locals and visitors since 1987. Catching a performance from either group is a great way to cap off a weekend getaway. Sarasota is also home to several luxury hotels and resorts, including the Art Ovation Hotel and the local Ritz-Carlton outpost. Those traveling with children will want to visit the well-known Mote Marine Aquarium & Laboratory and nearby Siesta Key beach, which is one of the country's prettiest stretches of coastline. For travelers seeking a beautiful Florida town with a cosmopolitan side, Sarasota delivers on every level.

Located on Gasparilla Island on Florida's southwest coast, Boca Grande feels like another planet from Florida's busier beach hubs. People who frequent this tiny town of under 1,000 residents appreciate its carefully preserved character and Old Florida feel. Boca Grande, a favorite escape among the rich and famous, prioritizes beauty, discretion, and a slow pace that makes it perfect for a relaxing weekend away. Over the years, Katharine Hepburn, Nick Saban, George H.W. Bush, and his family have all sought respite here. There's nowhere better to stay in Boca Grande than the famous Gasparilla Inn. With the tagline, "Florida as it was meant to be," guests can expect impeccable service and perfectly "Southern Prep" charm from the moment they walk onto the premises. The consistently uncrowded beaches are also exceptional here. Some travelers even say Boca Grande Beach is so sparsely populated that it feels private!

The Port Boca Grande Lighthouse and Museum is another popular attraction here for visitors. Constructed in 1890, the lighthouse was decommissioned in 1966 and has functioned as a museum since 1999. All in all, Boca Grande is ideally suited for a weekend getaway, particularly for those looking to unplug for a couple of days. The vibe here beckons visitors to spend a whole morning biking through town, then enjoy a long lunch at a local restaurant like Gasparilla Inn's kitschy-cool Pink Elephant or the ultra-elegant Tarpon Lodge. There are also plenty of local shops, like Sunsets of Boca Grande, that stock souvenirs. For a Florida weekend escape that feels simultaneously polished and unhurried, Boca Grande is the perfect destination.

Islamorada, a town that is actually comprised of six islands, is one of the most beautiful destinations in the Florida Keys, making it ideal for a low-key weekend getaway. Famous for its bright turquoise, crystal-clear water, and laid-back atmosphere, Islamorada truly operates on island time. The "Village of Islands" is an outdoorsman's paradise and is even called "The Sport Fishing Capital of the World." Fishing enthusiasts flock here in a bid to catch bonefish, snook, hogfish, and elusive tarpon. Some of the top-rated fishing charters in Islamorada are DirtyBoat Charters, 4Reel Fishing Charters, and Skins and Fins Charters. After a long day of offshore fishing, weekend vacationers should check out chill, oceanfront bars and grills like Papa Joe's Waterfront and Square Grouper.

Due to Islamorada's geographical layout, many of the hotels and rental bungalows here feel extremely secluded. This makes it the perfect weekend getaway for anyone looking to lay low for a couple of days. Pines & Palms Resort is an especially great escape. A family-owned property, this resort prioritizes privacy, with individual cottages for each temporary resident. Guests can also enjoy beautiful natural scenery and activities like paddle-boarding, kayaking, and private boat charters. As a matter of fact, all of Islamorada's islands — Indian Key, Lignumvitae Key, Lower Matecumbe Key, Plantation Key, Upper Matecumbe Key, and Windley Key — offer a variety of things for outdoor enthusiasts to enjoy. For example, the super scenic Windley Key Fossil Reef Geographical State Park offers guided tours, picnicking, and bird watching for the family.

One of Florida's most distinctive destinations, Key West offers an old-school, tropical destination. The southernmost tip of the United States is a place where flip-flops are acceptable attire everywhere and time moves just a little bit differently. Key West has long been immortalized in countless novels, Jimmy Buffett and Kenny Chesney songs, and literary lore. It was famously home to Ernest Hemingway, whose former residence remains a major draw, attracting artists, writers, and anyone with a slightly rebellious spirit. This history adds layers to a destination that could otherwise be boxed into being thought of as nothing more than a beach lover's paradise. As it stands, though, Key West's beauty lies as much in its surprisingly complex culture as it does in its physical appearance.

For weekend travelers, Duval Street is a must-visit destination. Packed with bars, restaurants, and live music venues, there's never a dull moment on Duval. Popular spots include the well-known Sloppy Joe's, colorful Rams Head Southernmost, and refined One Duval. Evenings in Key West typically center around good food, great music, and the island's world-famous sunsets. The nightly Sunset Celebration at Mallory Square is a great place for the entire family to take in one of America's best views during a weekend stay. Key West easily earns its place on this list by being unapologetically itself. It is beautiful because it's vibrant, quirky, and unapologetically itself. For beach bums and free spirits, this town offers an always unforgettable Florida getaway.

To put together this guide, I used my own knowledge of several of these towns due to my frequent stays in Florida. I also relied heavily on VisitFlorida.com, the official websites for various cities, high-authority travel sites including TravelZoo and Travel + Leisure, as well as blogs like Rachel's Findings and the official websites for stores, restaurants, and hotels.