12 days in Winchester & Jacksonville Itinerary

Explore the numerous day-trip ideas around Winchester: Purcellville (Catoctin Creek Distillery & Old 690 Brewing Company) and Gettysburg (Gettysburg Heritage Center, Gettysburg Museum of History, &more).

To find reviews, photos, where to stay, and more tourist information, refer to the Winchester online travel planner.

Washington DC to Winchester is an approximately 1.5-hour car ride. You can also do a combination of train and taxi; or do a combination of bus and taxi. Expect slightly colder evenings in Winchester when traveling from Washington DC in February, with lows around 27°F. Finish up your sightseeing early on the 18th (Sat) so you can catch the flight to Jacksonville.

Get out of town with these interesting Jacksonville side-trips: St. Augustine (The Ximenez-Fatio House, Castillo de San Marcos National Monument, &more). There's still lots to do: learn about wildlife with up-close encounters at Jacksonville Zoo & Gardens, look for all kinds of wild species at Theodore Roosevelt Area, walk around Boone Park, and test your team's savvy at popular escape rooms.

For photos, traveler tips, more things to do, and more tourist information, you can read our Jacksonville trip planner.

Traveling by flight from Winchester to Jacksonville takes 3.5 hours. Alternatively, you can drive; or do a combination of taxi and train. When traveling from Winchester in February, plan for warmer days and a bit warmer nights in Jacksonville: temperatures range from 70°F by day to 47°F at night. Finish your sightseeing early on the 25th (Sat) so you can fly back home.