Ready to explore every side of the Sunshine State? This is the ultimate Florida road trip guide—five unforgettable routes that take you from tropical islands and powdery white sand to hidden springs and bustling cities.
Whether you’re in it for the palm-lined beaches, scenic highways, or quirky roadside stops, these road trips show you Florida like you’ve never seen it before.
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1. Miami to Key West: A Tropical Odyssey on the Overseas Highway
There’s nothing quite like the drive from Miami to Key West.
Known as the Overseas Highway, this 113-mile stretch cruises across 42 bridges over turquoise water and through colorful island towns.
You’ll leave behind the high-rises of Miami and wind your way through the laid-back Florida Keys, each stop offering something unique.
Kick things off in Miami with a Cuban coffee and some street art in Wynwood before making your way south.
Make time for a pit stop at the legendary “Robert Is Here” fruit stand—where tropical smoothies and exotic fruits are the perfect road snack.
At Key Largo, explore John Pennekamp Coral Reef State Park, the first undersea park in the country.
As you continue, don’t miss Islamorada for a waterfront lunch or a tarpon feeding at Robbie’s Marina.
Further down, take in the stunning beach views at Bahia Honda State Park before rolling into the colorful, quirky streets of Key West.
Grab a slice of Key lime pie, visit the Southernmost Point marker, and toast your journey with a sunset at Mallory Square.
2. Tallahassee to Jacksonville: North Florida’s Hidden Heritage
This road trip feels like stepping into a time capsule.
Starting in Florida’s capital city of Tallahassee and ending on the Atlantic coast in Jacksonville, this route offers a blend of historic charm, Civil War history, and peaceful natural parks.
Begin in Tallahassee by touring the Florida State Capitol, then stretch your legs in Alfred B. Maclay Gardens State Park, known for its floral displays and tranquil walking trails.
As you drive east on I-10, swing through Madison, a picturesque town with beautiful antebellum homes and a surprisingly good coffee scene.
Stop in Lake City to visit Olustee Battlefield Historic State Park, the site of Florida’s largest Civil War battle.
Finally, arrive in Jacksonville, a city with urban energy and coastal relaxation. Browse art exhibits at the Cummer Museum, take a stroll along the St. Johns Riverwalk, or dig your toes into the sand at Jacksonville Beach.
3. Jacksonville to Destin: From Coast to Panhandle Paradise
From Jacksonville’s city skyline to Destin’s powder-white beaches, this road trip stretches over 300 miles and introduces you to the quieter, less-touristy side of the state.
It’s a favorite for travelers who want a peaceful, scenic route across North Florida.
Start in Jacksonville and head west along I-10. Revisit Tallahassee if you didn’t already explore it on the previous route.
Then continue on to Florida Caverns State Park in Marianna, where you can take a guided cave tour—yes, real caves in Florida!
It’s a surprising and fun detour with hiking trails and natural springs.
As you continue toward the Gulf, take time to discover the small-town charm of places like Chipley and DeFuniak Springs before finally arriving in Destin.
This beach town on the Emerald Coast is famous for its fishing, water sports, and jaw-dropping white sand beaches.
Finish your journey with fresh Gulf seafood and a sunset cruise in Destin Harbor.
4. Siesta Key to Key West: Gulf Coast to Island Bliss
If you’re dreaming of a long, scenic cruise down Florida’s Gulf Coast before ending in the tropical Florida Keys, this is your trip.
It’s the ultimate slow-paced adventure, starting on the laid-back shores of Siesta Key and ending in the non-stop fun of Key West.
Kick things off in Siesta Key, home to some of the softest sand in the country.
After a morning beach walk, head south toward Naples, a polished coastal city known for its palm-lined streets, upscale shopping, and dolphin-sighting piers.
Continue on to Everglades City for an airboat tour through the mangroves and swamplands—don’t forget your camera for alligator sightings.
As you hit the Keys, take your time through Key Largo and Islamorada, maybe even break up the drive with an overnight.
Eventually, you’ll reach Key West, where the live music, historic landmarks, and oceanfront bars make for a perfect finale.
👉 Follow the Siesta Key to Key West drive
5. Orlando to Siesta Key: Theme Parks to Tranquility
Orlando may be known for its high-energy theme parks, but just a few hours away is Siesta Key—where the pace slows down and beach vibes take over.
This road trip is all about contrast, going from thrill rides and roller coasters to soft sand beaches and sunsets.
Start in Orlando with a visit to Walt Disney World or Universal, then head west on I-4.
A great place to stretch your legs is Lakeland, where you can visit the Polk Museum of Art or walk along Lake Mirror’s promenade.
From there, continue to Sarasota and take a stroll through the Ringling Museum of Art or the Marie Selby Botanical Gardens.
Finally, end in Siesta Key, where you’ll find soft, powdery sand that feels like walking on sugar.
Whether you’re watching the drum circle at sunset or kayaking the nearby mangroves, this road trip ends with pure Florida relaxation.
👉 Explore the Orlando to Siesta Key drive
Final Thoughts: Florida, One Mile at a Time
These five iconic Florida road trips cover it all—beaches, springs, big cities, small towns, and everything in between.
You don’t have to do them all at once (though how fun would that be?), but even choosing one gives you a deeper, more colorful view of what the Sunshine State has to offer.
Whether you’re craving island vibes in the Keys, Gulf Coast sunsets, or historic pit stops in North Florida, there’s a road here with your name on it.
Pack the snacks, cue up your favorite playlist, and get ready for the Florida road trip of a lifetime.
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Booking a last-minute trip to Florida?
If so, we have you covered. Here are some top recommended tours and experiences!
Top Tours in Florida – Viator
Top Hotels In Florida – Booking.com
Looking To Get Around In Florida?
Check out rental car rates here! 🚗
