Road Trip!

Exploring Along the Way to the Florida Keys

A road trip is one of the most pleasurable ways to travel from Central Florida. Not only is it the most affordable travel option, it is arguably the most fun way to get a sense of what a place is really like. Plus, stopping along the way to your final destination can help draw out the adventure! And who wants to feel like they’re just going from Point A to Point B? 

The Florida Keys takes easy planning with an offer of some of the best combinations of fun. You can enjoy outdoor activities with world class beaches, fishing and diving, or take a break from the sun, with museums, unique art and amazing food. 

I suggest driving south, taking the historic U.S. 27 route through the center of Florida toward Miami, and onward to the Florida Keys, as it allows for finding some unique and picturesque stops along the way. As a family, we have braved the task a few times, and all agree on a few favorites I am happy to share. Are you ready to explore?

Haines City WINGS - Cameras ready for this photo op! The city’s Community Redevelopment Agency has created eight murals for a fantastic, but quick stop on this part of the Florida Mural Trail. Inspired by Colette Miller's 2012 Los Angeles street decor.

Spook Hill & Murals, Lake Wales - About an hour outside Orlando, enjoy a seemingly gravity defying experience at this haunted hill. Then go tour the 21 murals found in this city, like the one with a 1958 Thunderbird crashing through the wall on busy Lamson Street.

Lake Placid Murals - the beautiful murals are placed throughout the town and are part of the Florida Mural Trail. Most are easily seen with a quick drive-by, without need to even leave the car.

Coral Castle, Homestead FL - 1100 tons of coral, secretly hand-carved by one man? Yes, this is a must see!

Everglades National Park, Homestead FL - Iconic to Florida, you can drive through part of this 1.5 Million acre park, but to see the wildlife you will have to get out of the car and walk. Bug repellent highly recommended!

Miami’s South Beach - Drive through this historic Art Deco area to enjoy the iconic architecture and, of course, people watch - it’s South Beach after all. If you have a little more time to spare on your journey south, stop and see the 120,000 objects that have shaped our modern world at The Wolfsonian at FIU.

7 Mile Bridge - I mean, how else will you get there? One of the most fascinating drives ever!

Nobel Prize-winning Author Ernest Hemingway - Key West is now home of the Ernest Hemingway Home & Museum, where he and his over 50 cats once lived and frequented local bar Sloppy Joe's. Born in Oak Park, IL, Mr. Hemingway maintained a whimsical permanent residence here, where he once wrote To Have and Have Not and began work on Green Hills of Africa. 



Key West Museum of Art & History -housed in the 1891 Custom House, view an eclectic mix of art and history.

Key West Butterfly Conservatory - walk among 50 to 60 species of butterflies from around the world.

Christ of the Abyss, Key Largo - an underwater statue for divers. 


Capt. Tony’s Saloon, Key West - the oldest bar in Florida, it has a colorful history you can't miss.

Castaway’s, Marathon Key - the oldest restaurant on Marathon with waterfront views and 52 beers on tap!

Alabama Jack’s Beach Bar, Key Largo - this off-the-beaten-path bar & restaurant built over the water - a joyous good time.


Isla Bella Beach Resort- this Greek stylized resort is the perfect location midway between Miami & Key West.

Jules’ Undersea Lodge - unique stay in the Key Largo Underwater Park.

Baker’s Cay Resort, Key Largo, Curio Collection by Hilton - great nature trails, beaches, and is very pet friendly.

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