3 days in Virginia & Kentucky Itinerary

3 days in Virginia & Kentucky Itinerary

Created using Inspirock United States route planner

Make it your trip
Virginia Beach
— 1 day
— 2 nights


Virginia Beach

— 1 day

The Resort City

Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
Start off your visit on the 13th (Fri): get engrossed in the history at Military Aviation Museum, then kick back and relax at Sandbridge Beach, and then fly like a bird with a parasailing or paragliding tour.

To find maps, where to stay, and tourist information, read our Virginia Beach road trip planner.

Richmond to Virginia Beach is an approximately 2-hour car ride. You can also take a bus; or do a combination of train and bus. Expect a daytime high around 86°F in August, and nighttime lows around 72°F. Wrap up your sightseeing on the 13th (Fri) early enough to fly to Louisville.

Things to do in Virginia Beach

Outdoors · Parks · Tours · Museums


— 2 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Kick off your visit on the 14th (Sat): brush up on your knowledge of spirits at Willett Distilling Company, then sample the fine beverages at Barton 1792 Distillery, and then brush up on your knowledge of spirits at Jim Beam American Stillhouse. Get ready for a full day of sightseeing on the next day: explore the different monuments and memorials at Cave Hill Cemetery, see the interesting displays at Muhammad Ali Center, and then sample the fine beverages at Evan Williams Bourbon Experience.

To find traveler tips, more things to do, and other tourist information, you can read our Louisville road trip website.

You can fly from Virginia Beach to Louisville in 5 hours. Other options are to drive; or take a bus. August in Louisville sees daily highs of 86°F and lows of 68°F at night. Finish your sightseeing early on the 15th (Sun) so you can fly back home.

Things to do in Louisville

Breweries & Distilleries · Historic Sites · Museums

Side Trips

Virginia travel guide

History Museums · Wineries & Vineyards · Historic Sites
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.

Kentucky travel guide

Caves · Specialty Museums · Distilleries
The Bluegrass State
A diverse region of sprawling farmland and rich cultural heritage, Kentucky is the birthplace of American horse racing and home to the world-famous Kentucky Derby. While the cities of Lexington and Louisville experience the majority of the state's tourism, Kentucky is also a favorite among outdoor enthusiasts with its array of natural attractions, including the Cumberland Gap and the world's longest cave system at Mammoth Cave National Park. Take a tour through original Civil War battlefields to delve into the nation's history, or head to one of the many bourbon distilleries to learn more about Kentucky's most famous export.