The southern state of Florida is known for its sandy beaches, worldclass family theme parks, and trendy cities. But beyond the world-renowned tourist destinations, Florida is also home to some of the most charming and picturesque small towns in the country, each with its own unique character and fascinating bits of history.
From the historic streets of St. Augustine to the laid-back vibe of Seaside, these ten towns offer visitors a chance to slow down, soak up the local culture, and experience a different side of the Sunshine State. Whether you’re looking for scenic beaches, quaint shops, or top-rated local restaurants, these towns have something for everyone. Below we explore the 10 most beautiful towns in Florida and discover what makes each one so special.
St. Augustine stands out not just for its rich history as the oldest city in the United States, but also for its vibrant marine life and water-based activities. For those interested in exploring the local waters, St. Augustine fishing charters offer an unforgettable experience, allowing visitors to delve into the world of angling amidst stunning natural surroundings.
Amelia Island
This idyllic island off the coast of northeastern Florida offers pristine beaches, natural beauty, and charming historic towns. Visit the Amelia Island Museum of History, Fort Clinch State Park, and the Amelia Island Lighthouse.
Located off the northeast coast of Florida, Amelia Island is a secluded paradise known for its pristine beaches, natural beauty, and historic charm. Visitors can explore the island’s many historic sites, including the Amelia Island Museum of History, Fort Clinch State Park, and the Amelia Island Lighthouse. The island is also known for its many golf courses, including the Ocean Links Golf Course and the Amelia River Golf Club.
To grab a bite to eat, Salt at The Ritz-Carlton offers upscale dining with ocean views. From Caviar to Lobster to Baklava, Salt is the place to go. David’s Restaurant & Lounge offers fresh seafood in a casual setting. With an assortment of meat and seafood dishes, you can enjoy both the casual atmosphere and delicious food at the same time!
The Ritz-Carlton, Amelia Island offers luxurious accommodations and oceanfront access This is the perfect place to stay for a break from reality. The Addison on Amelia Island is another beautiful place that offers historic charm in a central location.
Anna Maria Island
This Gulf Coast barrier island is a laid-back paradise with pristine beaches and charming seaside villages. Don’t miss the sunset at Bean Point, visit the Anna Maria Island Historical Museum, and enjoy fresh seafood at The Waterfront Restaurant or The Sandbar Restaurant. For accommodations, check out The Beach Club at Anna Maria or the Harrington House Beachfront Bed & Breakfast.
Located just south of Tampa Bay, Anna Maria Island is a barrier island known for its pristine beaches, turquoise waters, and laid-back atmosphere. Visitors can rent bikes to explore the island’s quaint seaside villages, which include Anna Maria, Holmes Beach, and Bradenton Beach. Don’t miss the sunset at Bean Point, a secluded beach at the northern tip of the island that offers stunning views of the Gulf of Mexico. Other popular activities include kayaking, paddleboarding, and fishing.
For food, The Waterfront Restaurant offers fresh seafood while enjoying a beautiful waterfront view. The Sandbar Restaurant is known for its beachside location and seafood specialties, including their oysters, Two Docks clams, and Fish Tacos.
The Beach Club at Anna Maria offers luxurious accommodations with beach access and a rooftop sundeck. The Harrington House Beachfront Bed & Breakfast offers a cozy, romantic setting perfect for an intimate getaway.
Boca Grande
This small town on Gasparilla Island is a hidden gem, with unspoiled beaches, historic buildings, and world-class fishing. Visit the Boca Grande Lighthouse Museum or take a fishing charter, the world is your oyster!
The Gasparilla Island Lighthouse should be the first stop you make in your trip. This historical landmark opened in 1927 and has had many visitors from all around since. The Boca Grande beach is also a must, with white sand and the bluest water that will make you feel like you’re in the Caribbean! The Boca Grande Farm and Fish Market has fresh produce you won’t find anywhere else.
You can enjoy fresh, delicious seafood at The Pink Elephant for a casual lunch or dinner you’ll want to visit a second time. The Keylime Bistro and Loose Caboose offer delicious breakfast and brunch, where you can enjoy a sweet treat after!
You can book your stay at The Gasparilla Inn & Club, either in the Main Inn or its private cottages! The Palmetto Inn is a beautiful historic house with seven suites, originally built in 1900. Both of these lodging options are perfect for your Boca Grande getaway!
Mount Dora
This quaint town in central Florida is known for its charming downtown district, antique shops, and annual festivals. Mount Dora has an abundance of small-town southern charm that will make you feel like a local.
Begin your visit Visit the Mount Dora Museum of Speed, home to a collection of antique vehicles and modern classics. Each vehicle has a story you won’t want to miss! Another adventure would be to take a scenic boat tour on Lake Dora and see the beauty it has to offer. The Historic Downtown Mount Dora Electric Cart Tour should be on your list of things to do as well. This tour takes you through the town where you can learn about Old Florida.
Enjoy farm-to-table cuisine at The Goblin Market with its signature cocktails and the best comfort food. Open for lunch and dinner, this restaurant will leave you wanting more! The Bavarian Haus, a German style restaurant, is another fantastic option and allows you to try new kinds of dishes.
For lodging, consider booking a room at Lakeside Inn, Florida’s most historic hotel. Perfect for any kind of trip, this hotel is filled with rich history and will leave you with a great experience. The Mount Dora Historic Inn & Cottages is another great place in Downtown Mount Dora.
Key West
The southernmost point in the continental US, Key West is a colorful and quirky town with a rich history and stunning ocean views. Visit Ernest Hemingway’s Home and Museum, the Key West Butterfly and Nature Conservatory, and the Mel Fisher Maritime Museum.
Located at the southernmost point of the Florida Keys, Key West is a colorful and quirky town known for its tropical climate, historic architecture, and artistic community. Visitors can explore the town’s many galleries, museums, and historic sites, including Ernest Hemingway’s Home and Museum, the Key West Butterfly and Nature Conservatory, and the Mel Fisher Maritime Museum.
For food, Blue Heaven is a popular choice for its Caribbean-inspired cuisine and outdoor seating, offering a more casual vibe. Latitudes is another option that is more fine dining and beautiful ocean views.
The Marker Waterfront Resort offers modern accommodations in a central location that will make you never want to leave! Casa Marina Key West is another beautiful place to book, offering historic charm and beachfront access.
Sanibel Island
This Gulf Coast island is a paradise for nature lovers, with pristine beaches, abundant wildlife, and miles of bike trails. From exploring the wildlife to walking through the small town, Sanibel Island is a beloved part of Florida that should be on your bucket list!
Visit the J.N. “Ding” Darling National Wildlife Refuge and see the kinds of wildlife it has to offer. Home to Sanibel Island, the Manatees are the main attraction here that everyone wants to see! The Bailey-Matthews National Shell Museum is another place to seek out, especially on a rainy day. The Sanibel Island Lighthouse opened in 1884 and is still standing tall today, a must-see on your visit!
Check out Doc Ford’s Rum Bar and Grille for delicious American and Caribbean cuisine. The Blue Giraffe Restaurant is open for breakfast, lunch and dinner serving delicious meals all day!
The Sanibel Island Beach Resort is a beautiful spot to stay, just steps away from the beach! The Marriott Sanibel Harbour Resort and Spa is another fantastic option, set right on the beach with beautiful oceanfront views!
Seaside
Located on the Gulf Coast between Panama City Beach and Destin, Seaside is a picturesque town known for its pastel-colored cottages, white sand beaches, and laid-back vibe. Visitors can rent bikes to explore the town’s many parks and trails, including Seaside Amphitheater and Seaside Boardwalk.
This picture-perfect town on the Gulf Coast is known for its pastel-colored cottages, white sand beaches, and laid-back vibe. Visit the Seaside Farmers Market, take a yoga class on the beach, and enjoy Gulf-to-table cuisine at Great Southern Cafe or Bud & Alley’s. For lodging, consider The Pearl Hotel or Cottage Rental Agency.
The Seaside Farmers Market offers fresh produce and artisanal goods and is also a great way to spend your afternoon! The Great Southern Cafe and Bud & Alley’s are popular restaurants known for their Gulf-to-table cuisine.
The Pearl Hotel offers luxury accommodations with beach access and a relaxing spa. The Cottage Rental Agency offers cozy cottages and bungalows that are perfect for a romantic getaway or a family vacation!
St. Augustine
This charming town is known for its Spanish colonial architecture and historic sites. Visit the Castillo de San Marcos, the Lightner Museum, and the St. Augustine Lighthouse. For food, try The Floridian or Collage Restaurant. For lodging, consider Casa Monica Resort & Spa or St. George Inn.
Founded by settlers in 1565, St. Augustine is the oldest continuously occupied European settlement in the United States. Visitors can explore the town’s historic district, which includes the Castillo de San Marcos National Monument, the oldest masonry fort in the United States, and the Lightner Museum, a former hotel that now houses an eclectic collection of decorative arts.
Other must-see attractions include the St. Augustine Lighthouse & Maritime Museum, the oldest wooden schoolhouse in the United States, and the Fountain of Youth Archaeological Park, which commemorates the landing of Ponce de Leon in 1513.
Foodies will love The Floridian for its locally sourced ingredients and eclectic menu, including their signature cocktails! The Collage Restaurant is a popular choice for upscale dining with award-winning food and service.
For lodging, Casa Monica Resort & Spa is a luxurious option that reflects the town’s Spanish colonial architecture and is just steps away from the popular vacation adventures in St. Augustine. St. George Inn is a beautiful historic building that offers cozy accommodations where you feel like you’ve gone through time.
Tarpon Springs
This beautiful Greek-influenced town on the Gulf Coast of Florida is famous for its sponge diving industry, delicious Greek food, and vibrant cultural festivals. Known as “the sponge capital of the world”, tarpon Springs is only 45 minutes north of St. Petersburg and has much to explore.
The Tarpon Springs Sponge Docks has a variety of things to do and places to see. You can book a ride on the Spongeorama Cruise Lines and tour the beautiful water, and hopefully see some dolphins! The Rock and Reef Charters lets you book a trip with them, and they’ll take you along the Anclote River and to the beach!
Dimitri’s On The Water is a beautiful waterfront dining place with some of the best Greek food you’ll ever have. From various gyros to fish sandwiches, this restaurant will leave you feeling satisfied. For a quick bite, visit Hellas Bakery and Restaurant for more authentic Greek food!
The 1910 Inn is a historic Queen Anne style building, home to beautiful rooms and an even more beautiful garden. Another option to book is the Hampton Inn and Suites, with modern amenities and numerous rooms to choose from.
Winter Park
This charming Floridian town just north of Orlando is home to tree-lined streets, art galleries, and historic architecture. Known for its old-world charm, Winter Park is a lively town that’s perfect for a weekend getaway or much needed family vacation!
Visit the Charles Hosmer Morse Museum of American Art where you can discover beautiful collections by Louis Comfort Tiffany, including his personal jewelry and architectural items from his Long Island Estate. Take a boat tour on the Winter Park Chain of Lakes, an interconnected system of six stunning lakes you must see with your own eyes.
Enjoy contemporary American cuisine at The Ravenous Pig and a popular option to eat at. With dishes you’re guaranteed to love, this is a must-go on your trip! Prato is another spot where you can enjoy Italian style cuisine.
For lodging, check out The Alfond Inn or the Park Plaza Hotel. The Alfond Inn at Rollins College is a beautiful boutique hotel with luxurious amenities. The Park Plaza Hotel is located in the Park Avenue District steps away from shopping and history!