If you know our family, we love going on adventures and long road trips. On our latest road trip, we made our way from Chicago to Florida. If there’s one thing I’ve learned from road tripping, it’s that the kids are much happier if we add in stops (and snacks — lots and lots of snacks.) Plus, it’s much more fun to explore than sit around in the car, right?

So if you’re thinking of planning a trip (yes, go for it!) to Florida, here’s a rundown of our complete road trip itinerary from Chicago to Florida. Keep checking back for updates as I’ll have full details for you!

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Day 1: Chicago to Glasgow, Kentucky

The Ultimate Road Trip Itinerary from Chicago to Florida

Pit stop: Whenever we are on I-65, we always, always stop at Fair Oaks Farm for a potty break (clean bathrooms!), food, ice cream, or samples. (exit 220) If you have more time, I’d even suggest hanging out and seeing how this modern dairy farm operates. See what else you can do at Fair Oaks Farm.

Worthy Road Trip Stop: Our first major stop to stretch our legs was at Columbus, Indiana about an hour south of Indianapolis. The small Midwest town of Columbus, Indiana is known for their modern architecture. We had ice cream at an old-time ice cream parlor, Zaharakos, then let the kids unleash their energy at the playground at the Commons with the awesome Luckey Climber. We had fun in Columbus and hopefully will return again to check out more of the architecture around the city.

We hopped on the road again and reached our final destination of the day: Glasgow, Kentucky.

Where to eat: We wanted something close to our hotel, and El Mazatlan was just down the hotel. After quick research, we also found out it was a local favorite. The Mexican food was pretty good, but we were impressed with the large (and strong) 16 oz. margaritas for $4. Yes, you heard that right!

Where to Stay: Holiday Inn Express Hotel & Suites Glasgow

If you have more time:  Take time to explore Mammoth Cave National Park, the largest cave system in the world. Gary from Everything Everywhere shares his experience at Mammoth Cave.

Days 2 to 4: Chattanooga, Tennessee


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I can’t get enough of the beauty at #RockCity especially Lover’s Leap and the waterfall. Why Is it called Lover’s Leap? Legend says that a woman and a man from feuding tribes fell in love and eloped. The man was captured and thrown off the cliff. Eventually the woman followed after. . . . #instatravel #travelwithkids #travelbloggers #discovertheroad #travel #familytravel #postcardplaces #instago #instatravel #wonderlust #instapassport #travelwithme #roadtrip #familytravelblogger #bestintravel #trekarooing #roadtrip #travelmom #otheplaceswego #ChattanoogaFun @Chattanooga_Fun #Tennessee #visittennessee #visitchattanooga @SeeRockCity #waterfalls #myviewtoday #scenicview #instawaterfall #loversleap

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If there’s one thing you need to know about Chattanooga, it’s that there’s so much to do!

Things to Do:

  • Lookout Mountain’s legendary attractions – Ruby Falls for the tallest underground waterfall, Rock City’s incredible vistas, and Incline Railway’s one-mile trek up the mountain.
  • Explore the river and ocean at the Tennessee Aquarium. If you have time, definitely schedule a backstage tour.
  • Learn about Chattanooga aboard a Chattanooga Duck, an amphibious vehicle that goes on the road and water.
  • Try a moon pie (or 12) at the Moon Pie General Store.
  • Walk on the Walnut Bridge, the world’s longest pedestrian bridge.

Where to eat:

  • At Champy’s Fried Chicken, fried chicken is king here along with fried catfish and fried pickles.
  • Try Purple Daisy Café for finger-lickin’ BBQ and an insane banana pudding
  • Delightful BBQ (small portions) at Puckett’s Grocery located just a short walk from the Tennessee Aquarium.
  • Treat yourself to any of the amazing flavors at Clumpie’s. 
  • Looking for amazing burritos? MoJo’s by the base of Lookout Mountain is calling your name.
  • Try unique flavored donuts at Julie Darling Donuts.

Where to stay: SpringHill Suites by Marriott Downtown Chattanooga/Cameron Harbor

Related: Read all about our #ChattanoogaFun.

Day 4: Chattanooga, TN to Gainesville, FL

The Ultimate Road Trip Itinerary from Chicago to Florida

Worthy Road Trip Stops:

  • Since we passed by Georgia, known for their peaches, we just had to grab some peaches at Lane Southern Orchards. We were pleasantly surprised to find a peach tour on-site and was also able to try their homemade peach cobbler topped with their homemade peach ice cream. Yummy! Read more about this worthy road trip stop at Lane Southern Orchards.
  • Georgia is also known for pecans, so we also had to make a pit stop for pecan. Located right off the highway, Ellis Brothers Pecans, has pecans in every flavor. Imagine aisles and aisles of pecans (and samples). It was awesome! Plus, their restrooms were clean.
  • We couldn’t get enough of BBQ so we stopped by Smok n’ Pig BBQ. If you’re ever in the area, we highly recommend. Huge portions, great value (entrees includes salad bar AND dessert!), plenty of seating.

Where to stay: Holiday Inn Express & Suites Alachua – Gainesville Area

If you have more time:  If you happen to visit on a Saturday, stop by the Retirement Home for Horses at Mill Creek Farm. As the name suggests, 140 horses call Mill Creek Farm home. The admission is two carrots – a fabulous deal.

Day 5: Gainesville, FL to Winter Haven, FL


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We actually wanted to visit a natural spring today, but we were told there was a brown out due to rain. It was a hot and steamy day so we made our way to Gainesville.

Worthy stop: If the weather is on your side, make sure to bring bathing suits to the Depot Park’s splash pad. The park is pretty fantastic, too! We were all pretty famished and at the suggestion of Visit Gainesville tried out a BBQ spot in a convenience store. Pearl’s Country BBQ may have been the best BBQ we’ve had the entire time.

We drove a couple hours and made it to Central Florida. Yay!

Things to do: Kids loved exploring Hammock Hollow, the children’s garden at Bok Tower Gardens. The singing carillon is not to be missed!

Where to eat: Another local favorite, Harry’s Old Place, serves delicious seafood along with my kids’ personal favorite, gator bites!

Where to Stay: Hampton Inn Winter Haven

Related: Read all about our visit in Central Florida’s Polk County.

Day 6: LEGOLAND at Winter Haven, FL

The Ultimate Road Trip Itinerary from Chicago to Florida

Things to do:

What can I say? Any LEGO lovers will love this place. The kids could not get enough of the fun at Legoland Florida. We saw a Miniland on steroids, went on rides, found out that roller coasters are not going to happen anytime soon, ate apple fries, got wet at Legoland Waterpark, and then eventually rained out. It was a blast!

What to eat: Food at Legoland Florida and delivery from MJ’s pizza

Day 7: Tallahassee, FL


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We visited the Sunshine State’s capital, Tallahassee. and immediately wished we had more time to explore.

Things to Do: Explore Old Florida fauna, the zoo, and have a fun treetop adventure at Tallahassee Museum.

Where to eat:

  • Burger concoctions at Midtown Caboose.
  • Ice cream at Lofty Pursuits.
  • Delectable donuts from Donut Kingdom.

Where to stay: The super hip and trendy (and pet-friendly) Aloft Tallahassee Downtown

If we had more time: I think we would have enjoyed seeing the Capitol, as well as seeing wild manatees at Wakulla State Park. Learn more about the Capitol from Perceptive TravelTravel with Sara talks about exploring Tallahassee by Segway. Fun!

Read all about our visit to Tallahassee here.

Days 8-10: Destin, Fort Walton Beach, and Okaloosa Island, FL (The Heart of the Emerald Coast)

The Ultimate Road Trip Itinerary from Chicago to Florida

Oh, the beautiful Emerald Coast. Whether you want to fill your time with activities, lounging on the beach, or both, the Emerald Coast is fantastic.

Things to Do:

  • Walk along the Okaloosa Boardwalk and Okaloosa Island Pier for fantastic views of the emerald green waters.
  • Golf with dinosaurs at Wild Willy’s Adventure Zone, then cool off in the arcade.
  • Find dolphins on Southern Star Dolphin Cruises.
  • Get to know the area’s animals at the Gulfarium. Say hi to their albino alligator.
  • Bowl under the sea at Uncle Buck’s Fish Bowl, while sipping your fishbowl drink, of course.
  • Catch some rays at the beach. Kids can build sand castles with the white, soft sand.

Where to Eat:

  • Enjoy the atmosphere and awesome views of the beach and ocean at Al’s Burger and Beach Club on The Boardwalk. Don’t miss the blackened tuna salad or ahi tuna burger.
  • Have lunch at The Cowhead for amazing burgers.
  • Head a few doors down for snow cones at KC’s Sandbar and Grille. Whatever flavor you choose make sure to get it with ice cream and topped with homemade sweet cream.
  • Eat and bowl at Uncle Buck’s Fish Bowl. Try their gator bites here too.

Where to Stay: The Island by Hotel RL, a beachfront hotel

Day 11: Emerald Coast, FL to Huntsville, AL

We said goodbye to Florida and made our way back to Chicago. But not without checking out more places, of course. Unfortunately, since we were on running out of time, we didn’t get a chance to explore Rocket City.

If we had more time: Space exploration at U.S. Space & Rocket Center and food at Supper Heroes. Read about all the fun you can have at the U.S. Space & Rocket Center from Travel with Sara and Traveling Adventures of a Farm Girl.  Find out about all the family fun in Huntsville from Thrifty Jinxy,and yes, there’s more to explore than space as told by Litte Family Adventure. Hint: You must try Cotton Row Restaurant.

Day 12-13: St. Louis, Missouri


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We made the drive to St. Louis with just one quick fast food stop. We wanted to get to our final overnight stay of our trip, and still have time to explore a little of the city of St. Louis.

Suggested stop:  If you need to stretch your legs, The Paducah Riverfront in Paducah, Kentucky is a great place to walk while looking at historical murals. [Read about our side trip to Paducah here.]

Suggested stop: The hometown of Superman, Metropolis, IL, has plenty of photo ops including a huge statue of the man himself and a museum dedicated to all things Superman. [Read about our super trip to Metropolis, Illinois.]

Things to do In St. Louis:

  • The revitalized area around the Gateway Arch is finally complete! Check out the new museum, tour, and the surrounding areas.
  • Try the free Saint Louis Science Museum with dinosaurs and space exhibits. Don’t miss the outdoor area with rain garden and chickens.
  • If the St. Louis Cardinals are playing, you shouldn’t miss a game at Busch Stadium.
  • Get lost with the kids at the super cool City Museum.

Where to eat:

  • Try toasted ravioli and St. Louis style pizza from Imo’s pizza.
  • Get your ice cream fix at Clementine’s Naughty and Nice Creamery.
  • Try Afghan food at St. Louis’ first Afghani Restaurant at Sameem’s Afghan Restaurant in The Grove. Emperor Plate large enough for two people or one very, very hungry husband.

Where to stay: Drury Plaza Hotel St. Louis at the Arch

Day 13: Casey, IL

Ultimate Road Trip Stop in Casey, Illinois, home of 8 World's Largest Items (along with other Big items)

Time to head back home, but before doing we had to check out the collection of world’s largest things in Casey, Illinois.

Suggested Stop: If you’re looking for a wonderful farm to table place to eat, look no further than Firefly Grill in Effingham, Illinois. Make a stop at a Corvette museum. If you love to cook, then you’ll want an authentic John Boos cutting board. [Read more about our Effingham, Illinois.]

Yes, it may have been a little out of the way (shhh, don’t tell my husband!) but visiting Casey, Illinois was totally worth the small detour! The small town has 8 of the World’s Largest items, and also some other big items.

Find out what other big things you can see on the ultimate road trip stop at Casey, Illinois.

Have you driven to Florida before? What were some of your favorite things to do on the way there?

The ultimate road trip itinerary from Chicago to Florida

More about our Chicago to Florida road trip:

Chattanooga, Tennesee

Georgia Road Trip Stops

Central Florida’s Polk County

12 Hours in Tallahassee with the Family

St. Louis, Missouri

Casey, Illinois

Road Trip Survival