Florida's 13 Coolest Small Towns For A Summer Vacation

There are a lot of ways to have a "cool" vacation in the US State of Florida, starting from the waters bounding the endless beaches to the Disney scene. There are also many towns in between, such as these 13 towns that pack in an un-proportional amount of coolness within their small areas. 

Amelia Island

Amelia Island, Florida
Amelia Island, Florida. 

Part of the Sea Islands on the northeast coast of Florida, Amelia Island is a cool town with three miles of the un-crowded Main Beach and the state's northernmost Fernandina Beach. The latter comes with a unique history of having flown eight national flags, and a commemorating, yearly celebration, among many other festivals. Aside from the sun and sand, there is a golf resort, horseback riding, and some of the best nature with the most fantastic views around the island. The 200-acre Amelia Island State Park and the Amelia Island Trail offer explorative hikes with varying scenery into some truly-untouched natural beauty. History fans love visiting the Civil War Era Fort Clinch and the Amelia Island Museum of History, while everyone rejoices equally in Fernandina Beach's vibrant 50-block historical downtown, full of restaurants and shops. 

Anna Maria Island

Drone view of Bean Point Beach in Anna Maria Island
Drone view of Bean Point Beach on Anna Maria Island. Editorial credit: Noah Densmore / Shutterstock.com

Anna Maria is a 7-mile-small town set on the Gulf Coast island that remains largely undeveloped. The charming locale is full of unspoiled sights and opportunities to venture into the real wilderness. There is a free trolley for convenient access to various parts of the island, as well as the Monkey bus for a chilled-out, entertaining experience. Some of the cool activities include horseback riding on the beach, diving for treasures at the Bradenton Shipwreck site, and wildlife sightings, including a bird sanctuary, dolphins, manatees, and turtles. One must visit the Bean point beach, made of quartz rock that stays cool despite the sun, and the Coquina Beach, known for some of the best shelling in Florida. There's also the nearby Bradenton beach with a lively scene on its Bridge street and the cool Beer Can Island, just a short sail away.  

Cape Canaveral

Entrance to Kennedy Space Center Visitor Complex in Cape Canaveral, Florida
Entrance to Kennedy Space Center Visitor Complex in Cape Canaveral, Florida. Editorial credit: Allard One / Shutterstock.com

Often omitted on the map of the Sunshine State, Cape Canaveral packs a lot of cool action in a small setting. Home to the Kennedy Space Center, one can watch the everyday work pursuits and unobstructed views of the future-defining space shuttle launches by NASA and SpaceX. The town also comes with great un-crowded beaches for some traditional, chilled-out vacationing. The Canaveral National Seashore is renowned for 24 miles of undeveloped beachfront making it great for couples or to use at one’s own discretion. There’s also the cool cruise ship port to check out, along with the nearby Cocoa Beach, which is known to be one of the state’s best to party on vacation.

Captiva

Aerial view of sunrise in Captiva Island, Florida
Aerial view of the sunrise in Captiva Island, Florida. Editorial credit: Noah Densmore / Shutterstock.com

Captiva is set right off the mainland in the Gulf of Mexico as a cool beach townscape of candy-colored cottages. The bright island is renowned for the vibrant sunsets over the glistening sapphire waters that match this really cool vacation spot. One can stay in luxury at the South Seas Island Resort with its own 2.5 miles of the beach while heading out for sights, parasailing adventures, and lounging trips on a sailboat. With all the watersports imaginable, including fishing, there's no better vacation choice for those who love to stay active in the outdoors. As a quaint community with no traffic lights, it is galore for biking, unobstructed views, and endless hiking trails that dig deep into the island. The Bubble Room offers a memorable dining experience as a multi-colored restaurant with multi-themed cuisine on the menu. 

Celebration

Aerial view of Celebration, Florida
Aerial view of Celebration, Florida. 

Florida’s hidden gem, the off-the-radar town, comes with a one-of-a-kind perspective and setting to match its unique name. Originally developed by the Walt Disney Company, it was designed as a master-planned community to mirror Walt Disney’s ideals that he started with the Experimental Prototype Community of Tomorrow (EPCOT). The unique town also comes with a Riverdale-reminiscent local diner, beloved by the older couples who read the comics, as well as the younger crowd-fans of the series. Along with a cool history, Celebration is known as a real breather away from the decked-out Disney scene, which makes it the perfect chilled-out vacation destination.

Cypress Gardens

Just as it sounds, Cypress Gardens is a naturally scenic town that also comes with a really cool history. Decades before Disney World hit Florida, the town opened the state’s first-ever theme park, the Cypress Gardens Adventure Park, in 1936. Cypress Garden became world-renowned, with people coming from all around for the breathtaking botanical gardens and impressive water-ski shows. Although the theme park closed in 2009, the town holds onto its remarkable history with the perfectly-preserved garden portion inside the park. There is also a Legoland and boat tour offering joyful rides with different views of the lush townscape.

Everglades City

Everglades City, Florida
The small coastal town in the Everglades is a popular tourist destination with airboat rides along the Barron River. Editorial credit: Fotoluminate LLC / Shutterstock.com

Set at one end of the Wilderness Waterway, Everglades City boasts the moniker "the Gateway to the 10,000 Islands". It is also home to some of the best paddle-boarding, kayaking, and canoeing destinations in the state. Teeming with cool wilderness, one can endlessly explore the marshes, mangrove forests, and the bay's open waters via a chosen boating method. Those who do not wish to immerse themselves in the wilderness alone can take a guided tour of all the natural sights. For more wet and dry pursuits in the fresh air, there are scenic cycling excursions through old-growth forests, bird-watching, swamp buggy rides, and airboat tours. The rich ecosystem is also excellent for fishing, with plenty of locales to choose from and a varied array to catch.

Islamorada

Aerial view of Tropical Paradise Island, Islamorada, Florida Keys
Aerial view of Tropical Paradise Island, Islamorada, Florida Keys. 

The cool "Village of Islands" is a small town spread over five islands in the Florida Keys. Coming with an endless strip of pristine beaches, it is a true watersports heaven, along with hosting fishing tournaments throughout the year. If fishing for a game, one must try the unique bonefishing and sailfishing, which are most popular in the area. The area is also known for some of the best and freshest seafood. With water all around, there are many restaurants for a scenic dinner and drinks, in addition to views of the sun setting over the sea. Moreover, fishers and their families can enjoy a vacation on a budget, with many establishments offering to cook one's catch for a small fee. 

Palm Beach

Aerial view of Palm Beach, Florida
Aerial view of Palm Beach, Florida. 

The barrier island 10-square-mile beach proper comes with a cool in-town vibe and myriad ways to keep busy throughout the vacation. The many cool sights include The Breakers' glitzy hotel and refined property, comprising one of the nation's oldest luxurious accommodations. The active can bike along the Lake Trail while admiring homes and summer residences set as multimillion-dollar estates. The Worth Avenue comes with a line-up of well-known designer boutiques and art galleries. One must visit the Henry Morrison Flagler Museum, once home to Florida's railroad tycoon, for more culture. Upon becoming a hotelier himself, he gifted his third wife a Gilded Age mansion on the island as a present on their wedding way. 

Pensacola

Downtown Pensacola, Florida
Downtown Pensacola, Florida. 

The first city in Florida and a cool town today, Pensacola, was owned by various nations throughout its extensive history. To learn more about The City of Five Flags, one must check out the National Naval Aviation Museum, which also houses maritime artifacts on naval training. The Blue Moon Antique Mall offers unique finds and a setting like nowhere else, while the Jerry's Drive-In will satisfy any taste for a bite to eat before heading to the beach. The sunsets at Pensacola's beaches are the coolest natural feature in the town and in the wide-radius area around. Described as out-of-this-world beautiful, they can only be achieved from this locale and must be experienced to be believed. 

Sanibel

Aerial view of Lighthouse Beach on Sanibel Island
Aerial view of Lighthouse Beach on Sanibel Island. 

A laidback atmosphere brims on the streets, and tranquility emanates from the beaches of this small town set on the namesake island in southwest Florida. While many know Sanibel for the ultimate shelling opportunities, few know the reason behind it. Set uniquely perpendicular to Florida's coastline, the shells that the ocean washes ashore are truly one-of-a-kind. No one can leave the place without a hand or bag full of precious souvenirs for the loved ones back home. Although the hunt and the warm, calm waters hold many hostages at the beaches, one must check out the incredible nearby JN Ding Darling National Wildlife Refuge. The stroll-worthy fishing pier and the boardwalk winding through the marshes offer great views of the 19th-century lighthouse and the renowned western coast's spectacular sunsets. Void of chain establishments, one gets to dine on freshly-prepared dishes at locally-owned restaurants and mom 'n' pop shops.  

Stuart

Aerial view of Bathtub Reef Beach, Stuart, Florida
Aerial view of Bathtub Reef Beach, Stuart, Florida. Editorial credit: Noah Densmore / Shutterstock.com

Set on Florida's stunning Treasure Coast, Stuart is a cool little town known as the "Sailfish Capital of the World." While the moniker speaks for itself, those who come for the fishing and the seafood galore also get treated to the vibrant, pedestrian-friendly core abound by beautiful beaches. The active will find their perfect vacation fill in the area's bountiful watersports opportunities, while the relentless knowledge-seekers must visit the interesting Stuart Heritage Museum and the eye-opening Road to Victory Military Museum. For an especially cool Sunday morning, one must venture out to the weekly green market with live music hosted by the town just outside of the city hall between 9 am and 1 pm.

Vero Beach

Atlantic Ocean Beach at Vero Beach, Florida
Atlantic Ocean Beach at Vero Beach, Florida. 

Vero Beach is a barrier island tucked along the Treasure Coast in the area known as the Gateway to the Tropics. It is a shipwreck paradise for the modern-day pirates, as well as a naturally gorgeous locale of intense flora featuring many species, from northern Carolina to tropical palms. Many come to dive for treasures, while the quaint townscape is known for restrictive zoning rules and building heights. During walks along the miles of crowd-less coastline, one is greeted with pristine beaches for some alone-time with the sea. Just off-shore, the ruggedly picturesque reefs are cool today but were once the notorious bastards that claimed the lives of many ships passing through the area. The shipwrecks left valuables that divers relentlessly search for with metal detectors. One must come to the iconic Ocean Grill for dinner to check out the spot of the newly-sunk S.S. Breconshire. More cool attractions include McKee Jungle Garden and Lion Country Safari, as well as more restaurants with farm-to-table plates incorporating artisanal ingredients.

One is in for the coolest vacation when visiting these 13 towns in Florida. Featuring truly one-of-a-kind stories, sites, and adventures, one will achieve cool vibes and attain lifelong memories. 

Share