Unforgettable Florida Keys Road Trip: Driving with the Windows Down in Winter

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highway over the ocean leading to Florida Keys

Among the 50 states in the United States, Florida is definitely one of a kind. It’s a popular tourist destination year-round due to its nature, unique theme parks, and more. Plus, its southern location adds an extra draw for tourism during the winter. Mild weather aside, during the winter months you can avoid hurricane season. 



The Beach Boys penned the famous song “Kokomo,” wherein they sing about a spot near the Florida Keys called Kokomo. While Kokomo is not a real place, the Florida Keys are definitely real and just as dreamy as the fictional Kokomo, even in the winter. There are around 800 keys (a term derived from “cayo” which means “little island” in Spanish), but they are well connected to the mainland thanks to 42 bridges. Even with so many bridges, a trip from mainland Florida to the end of the connecting roads is possible in just a few hours. However, the iconic towns, white sand beaches, and wildlife of the Florida Keys will make you want to stay for longer than that.

Get close to ocean wildlife in Key Largo

Aerial view of John Pennekamp Coral Reef State Park

US Highway 1 runs along Florida’s Atlantic coast and all the way to Key West, which is the farthest key accessible by road. This “Highway That Goes to the Sea” begins its Florida Keys section in Key Largo just off of the state’s mainland. Key Largo is home to the massive John Pennekamp Coral Reef State Park (pictured above). Guests can get close to the vibrant sea life by taking a glass-bottom boat tour, canoeing, kayaking, snorkeling, or scuba diving. You can even get your scuba diving certification at the park by booking a scuba tour online.

Follow the highway to the town of Islamorada and hang out at Founders Park. Aside from a relaxing beach, the park has playgrounds, an Olympic-sized swimming pool, and walking trails. Among the sports amenities are basketball, pickleball, and beach volleyball courts along with a golf driving cage. Near the park is the quirky Rain Barrel Village famous for its local art, souvenirs, and the famous 30-foot-tall Betsy the Lobster sculpture. Continue the shopping spree at Robbie’s of Islamorada, where you can not only find more handmade items but also feed huge swarms of tarpon fish.

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Learn about efforts to protect endangered sea turtles

sea turtle at the Turtle Hospital in Marathon, Florida

Combine ocean activities with nature trails teeming with wildlife at Long Key State Park in Layton, Florida. Though Hurricane Irma affected the area, the park’s Golden Orb Nature Trail is still a sight to see. Its plant life varies from tropical trees to puddle-dwelling mangroves. Fiddler crabs and endangered white-crowned pigeons enjoy the trail as well, so make sure to keep the environment in mind while visiting. 

Florida has the most sea turtle nests in the entire United States. However, all species of sea turtles found along U.S. coasts are endangered. The Turtle Hospital in Marathon, Florida is working to help these animals and inspire others to get involved as well. The hospital’s sea turtles who are well enough to be returned to the sea get to do so in public at the nearby Sombrero Beach. If there is no turtle release during your time in the Florida Keys, you can still get a piece of the magic thanks to the hospital’s guided tours. These tours even allow tour guests to feed sea turtles. Reserve tour spots online to ensure availability ahead of time.



Check out the vibrant scenes of Duval Street in Key West

Duval Street in Key West

Paul Harris/Getty Images

At the end of US Highway 1 is Key West. It is the largest city in the Florida Keys and is known for its beautiful sunsets, history, and vibrant nightlife. As an important port city in its early years as a “U.S. property,” in 1823 the United States had to send the country’s navy to protect Key West against pirates, according to Keys History. To feel like a pirate yourself, visit the Key West Shipwreck Museum with centuries-old artifacts and tales of past ill-fated ships. Just minutes away is the Mel Fisher Maritime Museum with cannons and other well-preserved shipwreck items.

Along the southern shore of Key West is the self-explanatory Southernmost Point of the Continental USA monument. While it does not take long to visit this marker, nearby is the the Key West Butterfly and Nature Conservatory, wherein butterflies and birds roam freely among the conservatory’s guests. Finish your epic road trip at Caroline Street and the intersecting Duval Street. These historic streets are lined with old homes, shops, restaurants, and bars. Among the hotspots are Sloppy Joe’s and Joe’s Tap Room and RockHouse Live Key West which both combine good eats with quintessential Floridian atmospheres.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.