9 Prettiest Towns to Visit in Florida
What is in Florida that has captivated millions of tourists every year? In 2022 alone, the Sunshine State welcomed more than 130 million visitors, with 7 million of that chunk from international travelers. Perhaps it’s the theme parks in Orlando or the resorts in Miami that attract people to its tropical-like shores. Or maybe it’s simply because Florida is absolutely beautiful.
Discover the charm of this sunny state with some of the prettiest towns to visit in Florida! This list focuses on the smaller communities in the state to give them their time in the sun-lit spotlight, such as Crystal River’s waters, St. Augustine’s old-world allure, and Boca Grande’s posh feel. A combo of jaw-dropping oceanside views and compelling historical sites make these towns picture-perfect in many people’s eyes!
Naples
From its stunning coastline and art culture to its love for golf and high-end shopping, Naples exudes sophistication! Naples Beach alone continues to captivate tourists with its fine sandy shores, nearly 9 miles of coastline, and historic Naples Pier jutting out to the Gulf of Mexico. If that is not enough beauty for you, the Naples Botanical Garden might impress you with its tropical plants and vibrant flora.
After its natural wonders, hop to man-made art in the galleries of Gardner Colby and the Naples Art Institute. The latter has short-term workshops, wearable art fashion shows, art fairs, and free exhibits. Naples’ shopping scene is also a highlight for tourists, with luxe boutiques at Fifth Avenue (like Marilyn’s and Naples Soap Company) more than happy to give you some retail therapy.
St. Augustine
History is one of St. Augustine’s biggest appeal. Holding the title of the United States’ oldest continuously inhabited settlement founded by Europeans, this Florida city is a treasure trove of impressive historical sites and museums. Start with a tour via Old Town Trolley Tours to see sights and attractions that amuse, immerse, and educate visitors. Want to immerse yourself further? Explore the Colonial Quarter to experience St. Augustine’s three centuries' worth of history!
Other notable spots are the Lightner Museum and its Victorian-era artifacts, the Saint Augustine Distillery (circa 1907), and the Castillo de San Marcos fort. Even a simple stroll in downtown St. Augustine’s brick-lined streets is captivating and mesmerizing already.
Crystal River
Evident in its name, Crystal River is proud of its sparkling and pristine blue waters. Nicknamed “Home of the Manatee”, you can fish, kayak, and even swim with Florida manatees here! Head over to the Crystal River National Wildlife Refuge, particularly the freshwater springs of Three Sisters Springs, to see wintering manatees that visit to stay warm in Crystal River. Learn more about these majestic beasts and the local government’s preservation efforts via an eco-tour at Crystal River Preserve State Park.
Crystal River doesn’t just have its scenic waterways and wildlife—it is rich in history too! Get a glimpse of the state’s pre-Columbian heritage through burial and temple mounds at Crystal River Archeological State Park. After being amazed by Crystal River’s attractions, explore the city’s food scene with the Waterfront Social’s Tiki bar food and a good ol’ seafood boil from the Boil Yard.
Fernandina Beach
Like a New England town with palm trees, Fernandina Beach’s architecture is as interesting as its past. Known as the “Isle of Eight Flags,” this Amelia Island city has been under different nations since its existence, which you can learn more about at the Amelia Island Museum of History. Get the Amelia Island Carriage Tours to comfortably see Fernandina Beach’s well-kept Victorian-era structures from its past.
Don’t pass up on seeing Florida’s oldest bar, The Palace Saloon, which survived the Prohibition, Florida hurricanes, and even a deadly fire. Other highlights include the Amelia Island Lighthouse, the 1800s fort of Fort Clinch, the old hotel of The Florida House Inn, and the Isle of Eight Flags Shrimp Festival. The last one commemorates the city’s heritage with fresh seafood! Fernandina Beach is solid proof that there is more to Florida’s beauty than waterfront resorts.
Mount Dora
Mount Dora’s charms lie in its lakefront views, walkable downtown, and love for eclectic shops, outdoor cafes, and festivals. Just a short drive from Orlando, its small-town vibe can be enjoyed through bass fishing on Lake Dora, touring the iconic Mount Dora Lighthouse, and dining al fresco at any of the gourmet restaurants along 4th Avenue. Pisces Rising’s seafood and steak, Las Palmas’ Cuban fare, and the Florida-inspired cuisine of 1921 Mount Dora are all excellent choices!
Other than epicurean eats and waterside attractions, Mount Dora is also known as the “Festival City” for hosting more than 30 festivals a year. Some can’t-miss happenings are the Mount Dora Arts Festival and Jane Austen Fest—both February events celebrating arts and poetry. The biggest event, however, is the Mount Dora Craft Fair, which draws over 250,000 attendees every October. If you are in a party mood, come down to Mount Dora!
Boca Grande
With its breathtaking white-sand coastlines, unparalleled views of the Gulf Coast, and a luxurious hotel that has housed popular patrons over the years, Boca Grande is as grand as its name! This fancy coastal city on Gasparilla Island got its start when railroads connected it to the mainland, and affluent visitors started seeing the island’s beauty and potential. Enjoy the idyllic seashore setting of Gasparilla Island State Park, which also houses the Port Boca Grande Lighthouse Museum, an 1890 beacon that has operated as a museum since 1986.
For a taste of the ritzy life, stay at the Gasparilla Inn and Club, a historic hotel built in the early 1900s that has served the likes of Henry Ford and Katharine Hepburn. But if you’d rather stay outdoors, you can camp at the state park or the neighboring island of Cayo Costa, then pedal through Boca Grande’s scenery with the Boca Grande Bike Trail. It’s just you, the sun, the sea, and the views!
Venice
With a nickname like “Shark Tooth Capital of the World” and a Blue Wave-certified beach, many would not be able to resist visiting this Southwest Florida city. Make Venice Beach your first stop, which is easily accessible from the city’s Italian Renaissance-styled downtown. On your way there, you’ll pass by Ciao Gelato, the old-fashioned ice cream parlor, and the vintage cafe of The Soda Fountain.
Outside Venice’s photography-worthy coastline and downtown, the city is a hot spot for fossil hunters and marine science enthusiasts. The area was once a haven for pre-historic sharks, and as such, you’ll find many fossilized shark teeth. Explore this fascinating topic more at the Venice Museum and the yearly Venice Sharks Tooth Festival every April. Pretty and educational—that’s Venice!
Anna Maria
Although not as flashy as other Sunshine State towns, Anna Maria blows the competition out of the water with its astonishing coastline and close-knit community. Bean Point Beach is the favorite go-to for many Anna Maria vacationers because of its tranquil shores and wide sandy beach—perfect for secluded lounging and splashing! Meanwhile, Anna Maria Island Beach is closer to shops. The Sandbar Seafood and Spirits (try their grouper Reubens!) and the White Egret gift shop are conveniently nearby.
To see Anna Maria’s historical side, the Anna Maria Island Historical Society showcases the island’s past and notable events. Look at its Old City Jail, as well as the cottage that was swept into the sea but saved and preserved by locals. As a further testament to Anna Maria’s heartwarming closeness, the pier at the end of the street once had planks engraved by the locals, but is now also memorialized in the museum.
Dunedin
Delightful Dunedin continues to draw tourists with its lively sailing community, kitschy trolley tours, and bike-friendly neighborhood. Designated as a trail town, you’ll find that cyclists, skaters, and leisurely strollers are welcome and safe in its streets. Take your time absorbing the sights and drop by the Dunedin History Museum, Edgewater Park, the Penny Lane Beatles Museum, and the Stirling Art Gallery. If fishing and boating are more your style, the Dunedin Marina is more than happy to cater to your docking needs. For certified beach bums, don’t skip the stunning Honeymoon Island State Park and its white “sugar-like” sandy shores!
Dunedin’s Scottish heritage brings a touch of European charm to this coastal enclave. The town honors its Scotsmen settlers through the Dunedin Celtic Music and Craft Beer Festival every November. If you can’t make it, Cricketers British Pub will always be open at Bayshore Boulevard for a slice of Dunedin’s Scottish fare.
Uncover Florida's Hidden Beauty
It is easy to get distracted and mesmerized by Florida’s resorts and big cities—and no one can blame you. They are truly pretty! But as shown on this list, the Sunshine State’s good looks don’t stop there.
As the saying goes, “Beauty is only skin-deep,” and fortunately, the state is blessed with picturesque waterfronts and not-so-surface-level attractions, too. St. Augustine’s relics of the past, Venice’s pre-historic artifacts, Anna Maria’s neighborly vibe, and Dunedin’s fun Scottish background add so much to the state’s sunny demeanor and are truly some of the prettiest towns to visit in Florida!
