Morning: Depart Lawrenceburg early and head south on I‑65, then merge onto I‑75 S. Enjoy the rolling Indiana countryside and make a quick photo stop at the Indianapolis Motor Speedway visitor plaza.
Afternoon: Cross the Ohio River into Kentucky, then continue through the scenic Appalachian foothills. Arrive in Orlando by late afternoon and check into a hotel near International Drive.
Evening: Relax with a sunset walk around Lake Eola Park, rent a swan‑shaped paddle boat, and enjoy dinner at a downtown eatery.
Find HotelsMorning: Spend the morning at Walt Disney World’s Magic Kingdom, riding classic attractions and meeting beloved characters.
Afternoon: Head to Universal Studios Florida for thrilling movie‑themed rides and a behind‑the‑scenes look at Hollywood magic.
Evening: Return to downtown Orlando for a stroll along Church Street, sample local craft beers, and catch a live performance at the Dr. Phillips Center for the Performing Arts.
Find HotelsMorning: Check out of the hotel and begin the 6‑hour drive south on I‑4 and then I‑95, stopping for coffee at the historic St. Augustine Old City for a quick walk.
Afternoon: Continue through the Florida Keys, crossing the iconic Seven Mile Bridge. Arrive in Key West by late afternoon and settle into a boutique inn on Duval Street.
Evening: Explore the vibrant nightlife of Duval Street, enjoy fresh seafood at a waterfront restaurant, and watch the sunset at Mallory Square where street performers gather.
Find HotelsMorning: Tour the historic Ernest Hemingway Home & Museum, meeting the famous six‑toed cats and learning about the author’s life.
Afternoon: Cycle or stroll to the Southernmost Point Buoy for photos, then relax on the white sands of Fort Zachary Taylor Historic State Park.
Evening: Dine at a rooftop venue on South Street, savoring Caribbean‑inspired cuisine while reflecting on the road trip.
Find HotelsIf you have extra time, add a full day in Orlando to visit SeaWorld or the Orlando Science Center, and consider a night‑time boat tour of the Florida Keys. To shorten the trip, skip one of the theme parks and spend the saved day exploring more of Key West’s islands, such as a quick ferry ride to Islamorada for snorkeling.