A Two-Week Road Trip through the Sunshine State

Located just 90 miles north of Cuba, Key West offers visitors a serene beachfront getaway rife with resorts, sites, and activities. Explore submerged wonders by SCUBA diving or snorkeling at the Vandenberg, a sunken ship turned reef that stands as the southern anchor of the Florida Keys Shipwreck Trail. Fish for marlin, tuna, sea trout, or grouper on one of Key West’s party boat charters. Embrace your inner child by swimming with dolphins off the coast. And when your day in paradise begins to wind down, grab a margarita and watch the sky turn orange and pink from one of the island’s many beaches. When departing Key West, you will take Florida’s famous Seven Mile Bridge, which offers drivers stunning views of the Atlantic Ocean. On your way north, stop by Theater of the Sea and interact with the many species of marine life they work to preserve. 

Driving north for just over three hours on breathtakingly beautiful bridges and waterfront roads, you will find yourself in Miami, one of America’s cultural hubs. The most iconic city in South Florida, Miami offers guests an unbelievably wide array of experiences. We recommend venturing into as many neighborhoods as possible during your stay in the Magic City. Stroll down Ocean Drive and gaze at the historic art deco architecture lining the street. Visit the vividly realized street murals in Wynwood, one of Miami’s up-and-coming neighborhoods. Grab some chicharrones or croquettes at Versailles, “the world’s most famous Cuban restaurant,” located on Calle Ocho in the heart of Little Havana. And when the sun goes down, partake in Miami’s world-renowned nightlife by dancing your feet sore at LIV, one of South Beach’s many clubs. As you continue your road trip west, grab a bite at Pit Bar-B-Q, a Latin-inspired, tender-rib-serving, music-playing local favorite. 

After a few days of metropolitan life, indulge your adventurous side by driving west into some of the most biodiverse wilderness on the planet. Since its demarcation as a national park in 1934, the Everglades has offered travelers sprawling seas of grass, thriving wildlife, and unparalleled nature-based activities. Some essential Everglades experiences include riding an airboat through marshes, eating alligator bites, biking Shark Valley’s 15-mile route, and camping underneath the breathtaking Everglades night sky. And though the natural beauty of the Everglades may be overwhelming, it is important to remember that these precious ecosystems are fragile and require that individuals exercise the utmost respect when visiting them. If you haven’t had enough time in nature, stop by Butterfly World on your way up to Orlando to walk among monarchs, zebra wings, and hundreds of other remarkably colored species. 

Four hours north of the Everglades, you will find yourself In Orlando, the Theme Park Capital of the World. A trip to this city would not be complete without visiting The Most Magical Place on Earth. Comprised of four separate parks, Walt Disney World offers visitors of all ages an experience of childhood wonder like no other. Whether sloshing down slides at one of its two water parks, zooming through the stars on Space Mountain, or traveling between different cultures at Epcot, you will constantly be awestruck during your time at Walt Disney World. For those more inclined to enjoy thrilling rides, we recommend dedicating some of your time at Universal Orlando Resort. Universal’s roller coasters have been drawing in adrenaline junkies from across the globe for decades and are the kind of high-octane fun that you won’t want to miss out on during your road trip. As you make your way to Florida’s northeast coast, visit the iconic Daytona International Speedway for the chance to watch some of the world’s best race-car drivers put the pedal to the metal. 

After the nonstop excitement of Orlando, relax by driving northeast for a few hours to the oldest city in the United States: St. Augustine. Rife with historic sites and beautiful Spanish colonial architecture, this coastal city is the perfect place to unwind for a couple of days. Walk along St. George Street, a pedestrian-only thoroughfare where some of the city’s most popular museums, stores, and restaurants reside. Visit the Castillo de San Marcos, a masonry fort with a deep and rich history stretching back almost 400 years, located right by the ocean. Stop by the locally owned and operated St. Augustine Distillery, where the world-class staff brews award-winning spirits made of regionally sourced products. And when night rolls through St. Augustine, discover the city’s dark history by taking one of its paranormal tours. Upon heading to the final destination of the road trip, pay a quick visit to the World Golf Hall of Fame located just outside of St. Augustine.  

To finish off the road trip, drive west toward Florida’s panhandle and into its capital city. Tallahassee is home to a wide array of sites to explore and a diametrically different culture than that of more Latin-influenced areas like Miami. Learn some of the south’s deep history by visiting Tallahassee’s wonderfully preserved 19th-century homes and plantations. Stop by Florida State University, the oldest college in the state and the home of the Florida State Seminoles. Explore Apalachicola National Forest, located on the Gulf of Mexico, home to some of Florida’s most iconic wildlife such as alligators, bald eagles, and black bears. Visit the city’s bustling downtown market on the weekends and sample locally grown produce and freshly baked bread. And when your days finish up, stay downtown to experience Tallahassee’s bustling bar scene.  

Florida’s diverse metropolitan areas, thriving wilderness, and abundance of historic sites make it the perfect place for your next road trip.