13 days in Waynesboro, Kissimmee & The Villages Itinerary

Waynesboro, is an independent city in the Commonwealth of Virginia. Start off your visit on the 14th (Fri): explore the different monuments and memorials at Dean Cemetery, then take a memorable drive along Skyline Drive, and then take your sightseeing to a higher altitude at Skyland Stables. On your second day here, examine the collection at Woodrow Wilson Presidential Library and Museum and then skim along the rocks with a canyoning and rapelling tour.

To see ratings, maps, traveler tips, and other tourist information, use the Waynesboro trip planning tool.

Columbus to Waynesboro is an approximately 6.5-hour car ride. In October in Waynesboro, expect temperatures between 68°F during the day and 45°F at night. Finish your sightseeing early on the 16th (Sun) so you can drive to Kissimmee.

A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.

Bring the kids along to Old Town and Busch Gardens Tampa Bay. You'll find plenty of places to visit near Kissimmee: Merritt Island (Space Shuttle Atlantis & NASA Kennedy Space Center Visitor Complex) and Legoland Florida Resort (in Winter Haven). Pack the 22nd (Sat) with family-friendly diversions at Fun Spot America. Next up on the itinerary: get a dose of the wild on a nature and wildlife tour, find something for the whole family at Old Town Sling Shot & Vomatron, stroll around Kissimmee Lakefront Park, and examine the collection at Museum of Military History.

Plan my day in Kissimmee using traveler tips and tourist information provided by Klarna Trips.

Explore your travel options from Waynesboro to Kissimmee with the Route module. Expect a bit warmer weather when traveling from Waynesboro in October: highs in Kissimmee hover around 84°F, while lows dip to 68°F. Cap off your sightseeing on the 22nd (Sat) early enough to go by car to The Villages.

The Villages is a census-designated place (CDP) in Sumter County, Florida, United States. On the 23rd (Sun), browse the different shops at Lake Sumter Landing, then see the interesting displays at Eisenhower Regional Recreation Center, and then don't miss a visit to Brownwood Paddock Square. Get ready for a full day of sightseeing on the next day: tee off at Twisted Oaks Golf Club, take a tour by water with Boat Tours & Water Sports, and then play a few rounds at Nancy Lopez Legacy Golf & Country Club.

For maps, more things to do, reviews, and more tourist information, you can read our The Villages online trip itinerary planner.

Drive from Kissimmee to The Villages in 1.5 hours. Alternatively, you can do a combination of bus and shuttle; or take a bus. In October, daytime highs in The Villages are 83°F, while nighttime lows are 65°F. You will have some time to spend on the 25th (Tue) before leaving for home.