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Florida is the national getaway for the summer and a widely visited state among global tourists for its beaches, sunshine, and “happening” culture. With the city of Orlando and the Disney scene, as well as many other recognized cities, towns, resorts, islands, and wildlife landscapes like the Everglades, it is no wonder that Florida ranks high on the coolness spectrum.
Despite the sweltering heat, summer crowds, and even the moniker “Sunshine State,” Florida remains an unconquered cool destination. Find respite from all the nuances and relinquish only the best by visiting one of the smaller towns. These 13 small towns are a breathtaking scene that calls your name for the most memorable summer vacations of a lifetime.
Captiva Island is a long beachscape in the Gulf of Mexico, off the mainland. There is only one town, Captiva, and cool sights every which way, with water on one side and wilderness on the other. Admire the candy-colored cottages lining the shore and striking sands against sapphire waters with renowned sunsets of yellows, reds, and violets. The bright island is a cool vacation spot where you can stay luxuriously at the South Seas Island Resort with parasailing adventures, sunbathing, and lounging trips on a sailboat from its own 2.5-mile beach. Enjoy watersports, fishing, and other fresh-air pursuits under the open skies, Florida’s relentless sunshine, and a gentle sea breeze.
Explore the quaint community with no traffic lights and unobstructed views on a bike. Stop by the thematically colorful Bubble Room for multi-themed cuisine along the main thoroughfare. There are over 15 miles of beaches strewn with 250 different types of shells, unique wildlife sightings, and those enchanting sunset views over a picnic. Take a hike along the trails into the island’s heart, a refreshingly tropical paradise, and check out the nearby 330-acre wildlife preserve, or play golf at the resort’s picture-perfect course along the water.
This pretty town on the northern tip of the beautiful Amelia Island, within the northernmost stretch of Florida, offers a real cool vacation with easy access and a remote feel. The barrier island encompasses glorious nature as well as a pristine coastline with thirteen miles of sandy shores. Enjoy a morning stroll along the island with 40 public beach access points and choose a spot to picnic, play in the water, and dig your toes in the sand. Eat, drink, and be merry at Palace Saloon, a bona fide Florida’s oldest bar in operation since 1903 that stayed open through the Prohibition with 3% “near-beer” and awesome cocktail concoctions today, like Pirate’s Punch.
The Salty Pelican in town serves signature broiled oysters, while Timoti’s Seafood Shak is renowned for cooking only the daily catch. “The Isle of Eight Flags” was established in 1562 and has a deep history of wars and changing flags until it finally belonged to the US after the Civil War. Discover the vibrant heritage involving pirates, brothels, and casinos in the harbor town. Fernandina Beach is also part of the National Main Street Program, a project based on preserving economic vitality in older and historic downtowns. Stroll along the thoroughfare under a laid-back vibe, with boutique shops and restaurants surrounded by thriving wildlife.
Established in the early 1900s, Fort Pierce is a cool destination for any taste amid an old Florida vibe. Take a stroll through the 156-mile-long Indian River Lagoon, the US’ most biologically diverse estuary, which houses 4,000 fauna and flora species for bird watchers and nature lovers. The offshores are bountiful in natural and artificial reefs, making them a real snorkelers and scuba divers’ haven for underwater adventures.
The “Sunrise City” is a tiny town with captivating antiquity and spectacular nature. Check out the waterfront downtown area with a number of excellent restaurants for seafood that is served up just cooked from the sea. As a former fishing village, there’s a jutting outscrape of rocks still used by anglers, which also poses an idyllic place for the best views and clearest water for sunbathing, diving, and swimming in the depths without the beach crowds.
Havana, a historic town in Gadsden County, is just 14 miles north of Tallahassee. The railroad town, named by a local schoolteacher and established by families from the nearby town of Salem, has thrived through tobacco growing since 1829. Its hand-wrapped cigars resembled those from its namesake city in Cuba, until a fire in 1916 destroyed much of the business portion, including twenty-five buildings.
Havana turned to antiquity, transitioning to the present-day tourism industry. It is a colloquially underrated destination, with the best antique shops, art galleries, and specialty shops to buy unique home décor, antiques, and vintage collectibles. Take a stroll through the historic streets with a vibrant “Little Havana” vibe in a Miami neighborhood. The town of under 2,000 residents warms hearts with its unique history and laid-back lifestyle.
Islamorada is a popular summer vacation destination and a quick two-hour getaway from Miami. The cool town is a love child of the Florida Keys, with beaches and a tropically-infused atmosphere perfect for romantic dates over cocktails, seaside excursions, and exotic eats. The upscale, small-town vibe appeals to those looking to relax in style and do some boutique shopping, while culture fans enjoy history at the many museums and modern attractions like seafood restaurants and boating under lots of sunshine.
Book a villa at Hadley House near the center for the best access to the beach, watersports, and downtown scene within five minutes by car. The boutique hotel sits partially on the beach, with complimentary on-site kayaking and paddleboarding as well as optional private jet-ski tours around the Keys. Check out the local funky breweries of Florida Keys Brewing Co. and Islamorada Beer Company, with Keys-inspired ingredients like key lime, starfruit, and honey.
The picturesque town of Key Largo is an oceanfront paradise along the Florida Keys chain, with easy access from Miami. Immerse yourself in the tropical vibe and slower-paced life under enchanting sunsets. Check into one of the chic hotels overlooking the ocean and check off places on the restaurant scene.
The Playa Largo Resort & Spa is a luxury Key Largo resort with a vast, secluded shoreline facing the stunning Florida Bay. You can spend days basking along the beachscape or enjoying water sports like fishing, sailing, jet skiing, and swimming. You don’t have to leave, with all pursuits at hand and restaurants with bars waiting on-site to recharge you, along with various entertainment to diversify each evening.
There’s no cooler town without an oceanfront in Florida than Lakeland, with so much to see and do. You will feel right at home and forget the traditional way to escape in the Sunshine State after experiencing all the town has prepared for you without crowds. Enjoy sightseeing strolls amid marvelous architectural feats by the legendary Frank Lloyd Wright.
The award-winning bread from the Born & Bread Bakehouse is worthy of gorging yourself on without guilt; you can walk off amid 10,000 flowers along the naturally beautiful Hollis Garden. Lakeland, one of the state’s quaintest towns, is made for chillaxing pursuits in tranquility. Take picturesque walking and jogging trails along Lake Mirror, followed by cooling dips. Check into the downtown Terrace Hotel, which is in a beautiful location and a short drive from Orlando’s theme parks.
New Smyrna Beach
Head to Smyrna Beach for a laidback, luxurious summer vacation, and never look back. This one-of-a-kind small coastal enclave is replete with sights and activities to diversify every day. Find Smyrna Beach along Florida’s Central Atlantic Coast and immerse yourself in small-town charm with big-city flavors, like the coveted culinary scene to be discovered in the best way known to men. Visit the Canal Street Historic District, which features architectural marvels interspersed with your favorite shopping, dining, and entertainment venues, among other exciting attractions.
The quintessential town is a long-beloved family destination with a charming main street leading to the water, a laid-back atmosphere, and beautiful nature’s embrace all around. Check out the 17 miles of pristine white sand beaches and visit the Indian River Lagoon with over 400 different birds, dolphins, manatees, and other wildlife. Choose your way to have fun in the outdoors, from hiking trails and waterways to surfing the highest waves in the whole region.
Punta Gorda is a cool beach town along I-75 on the south-central Gulf Coast, with a beautiful, restored historic district and many natural attractions. Head on a Harborwalk stroll, replete with views over waterside shopping and leisurely pursuits. Venture deeper into the streets lined by huge royal palms and tin-roofed homes featuring wide verandas, brick lanes, street lamps, and benches to absorb the overwhelming scenery under the old Florida vibe.
With a population of 20,320, Punta Gorda is a cool getaway for adventurers with outdoor activities like biking, boating, stand-up paddle boarding, canoeing, and kayaking. Stop by some of the most unique and charming hotspots like the Peace River Botanical Garden, Peace River Wildlife Center, and Alligator Bay Distillers. You will find more stores at the waterfront Fishermen’s Village on Charlotte Harbor, including gifts, clothing, and specialty finds, as well as seven restaurants, a military heritage museum, a 98-slip marina, and more luxury villas.
St. Augustine is one of those Florida destinations that keeps giving on every visit with a new dose of cool, white-sand beaches, history, the food scene, and plentiful other attractions. Juan Ponce de León, a Spanish explorer, stumbled upon the area in the early 16th century during his search for the Fountain of Youth. Since European settlement in 1565, the “Nation’s Oldest City” has become more beautiful, lively, and exciting than ever. Stay at the Casa Monica Resort & Spa at the heart of the city’s Historic District for beyond top-notch services and walking distance to the award-winning San Sebastian Winery and Castillo de San Marcos.
Enjoy one-hour access from Jacksonville and immerse yourself in the cozy small-town vibe. Relish in the wealth of locally-owned cute cafes, restaurants for any style, and charming boutiques under the all-encompassing oceanfront atmosphere. Stroll and relax with a picnic along the soft stretch of sand and feel the gentle ocean lapping at your feet. Get your blood pumping at the refreshing Splash Park or play sand volleyball, and check out the fishing pier for the best views. Learn a new skill like stand-up paddleboarding, surfing, boogie boarding, or kiteboarding before heading for a well-deserved meal at the oceanfront. The historic center is only 15 minutes away, with its own wealth of eateries and popular attractions like museums and sights that date back to the town’s origin.
St. Pete’s Beach
St. Pete’s Beach is a coastal town with gorgeous beaches, stellar restaurants, and top-notch art museums, all under a cool ocean breeze. It is the most underrated gem in Florida, in the shadow of its big brother, St. Petersburg, but epic in a whole other way, with just as easy access from Miami. Check out the cute downtown with virtually no traffic and under 15 minutes to big city life.
Book a room at the boutique Kimpton Hotel Zamora, a Mediterranean-inspired property near the beach and just ten minutes from the center. You will have an expansive suite with balconies overlooking the Gulf of Mexico for a luxurious stay at an affordable price that will feel too good to be true, and you may never want to leave. Enjoy all the cozy modernity at the dog-friendly property all you want, and make it to the rooftop bar for an epic evening atmosphere; ditto the sunset.
The town edging a barrier island by the same name along the Treasure Coast is your gateway to the tropics. Explore the “shipwreck paradise for the modern-day pirates” with gorgeous local nature. Its diverse and intense flora ranges from northern Carolina trees and plants to tropical palms. The quaint town with restrictions on building heights makes for endless views and miles more of crowd-less coastline. Head to the pristine beaches for one-on-one time with the sea and the just-off-shore, ruggedly picturesque reefs. These cool underwater bastards were notorious for destroying many passing ships, claiming lives, and drowning treasures.
The newest sunk The S.S. Breconshire is an iconic shipwreck with a restaurant right above the spot where you can see divers with metal detectors. Stroll through the McKee Jungle Garden and Lion Country Safari, and switch from the sea food scene to some farm-to-table plates incorporating artisanal ingredients. Vero Beach is the “Hamptons of Florida,” a sophisticated getaway with luxurious accommodations that is a perfect place to chill and explore via golf cart. Stay at Vero Beach’s Costa d’Este, a glamorous hotel that brings Miami flair like fine dining, spa treatments, craft breweries, and boutique shopping.
Cypress Gardens is full of refreshing vibes that make you want to stay outside from day to night. The naturally scenic small town with a really cool history opened the state’s very first theme park, the Cypress Gardens Adventure Park, in 1936, decades before the Disney scene hit Florida. It became a target for tourists from around the globe who wanted to experience new rides under Florida’s loving sunshine, along with breathtaking botanical gardens and impressive water-ski shows.
The park closed in 2009, but the town, with its remarkable history and manicured gardens, attracts new visitors to this day. Cypress Gardens is also home to Legoland Florida and activities for any group, like boat tours for different views of the town enclaves within nature’s lush embrace. Enjoy a cool first-time experience in Cypress Gardens, and it will become your favorite scenic destination for years to come.
Each unique town is full of cool sights and pursuits to spend every day of a summer vacation in a new, cool, and fun way. Immerse yourself in cool waters or take a refreshing hike through the natural landscapes. Absorb the cool vibe along the streets and within cool historic districts amid architectural wonders.
Choose from the nation’s oldest city, underrated gems, and island remoteness for a personalized vacation in Florida. Chillax, enjoy thrilling adventures, mix it up, and you’ll remember the town as the coolest getaway ever.