Trip Ideas

Itineraries for Chesapeake Vacations

One region, many destinations, unlimited experiences!

Located in the heart of Coastal Virginia, Chesapeake boasts a rich cultural history, scenic natural wonders, delicious dining and abundant shopping.  Stay in Chesapeake and explore all the city has to offer.  And remember that with major highways and convenient accessibility from Chesapeake to neighboring cities, you can experience the very best of Coastal Virginia by starting in the center of it all!

These suggested tour itineraries have been developed to highlight Chesapeake's special tourism features and to assist travel planners in designing trips throughout the city and the region.  These itineraries can be enjoyed by groups or individual travelers.

Into Chesapeake's Outdoors Pack your bags, grab your car keys, buckle up, and take on the open road to experience Chesapeake. More
Exploring Nearby If you're looking for things to do near Chesapeake, VA, consider a day trip! More
Scouting Merit Badges Chesapeake offers many opportunities for Scouts to earn merit badges.  Here are just a few... More
A Culinary Tale A family owned and operated restaurant located in beautiful downtown Rescue, Virginia on Jones... More
Southern Hospitality Visit one of the oldest churches in America.  For nearly four centuries, Historic St.... More
Birding & Wildlife Viewing Since the 17 th  century, the Great Dismal Swamp National Wildlife Refuge has provided... More
Get Wild! Head to Norfolk to the Virginia Zoo.  This zoo is home to 350 animals, on 53 acres of... More
Shop 'til You Drop! Enjoy breakfast at your hotel then head down to Historic Williamsburg to the Prime Outlets. ... More
Ready, Set, Paddle! Enjoy a hearty breakfast at Cracker Barrel Restaurant before heading out to one of the only two... More
Un-Wine'd Tour After breakfast at your hotel, board the bus for a short drive to Historic Williamsburg... More
  1. Into Chesapeake's Outdoors - Take on the open road for this WanderLOVE experience!
  2. Exploring Nearby - A great starting point for your next adventure.
  3. Couples Cozy Getaway in Chesapeake - This couples getaway is sure to be a hit with your significant other!
  4. Fall Family Adventure - Take the family and see what fall looks like in Chesapeake!
  5. A Culinary Tale - Friendly atmospheres and fresh ingredients are just the beginning of this culinary tale.
  6. Earn Your Scouting Merit Badge - Chesapeake offers many opportunities for scouts to earn merit badges.
  7. Southern Hospitality - This tour takes you back in time in historic Smithfield, VA! This quaint, small town on the Pagan River was incorporated in 1752 and is still a working, living, breathing town.
  8. Birding & Wildlife Viewing - Chesapeake, VA - Birding and wildlife watching is one of the fastest-growing hobbies in the country. 
  9. Get Wild! - Get wild with us! This tour takes students through the African desert in search of African elephants and lions. 
  10. Shop 'til You Drop! - Looking for some retail therapy? From Premium Outlets in Williamsburg to Greenbrier Mall in Chesapeake, we have the right prescription for you!
  11. Ready, Set, Paddle! - From Lake Drummond to Currituck Sound, enjoy the sights and sounds of the area's unique waterways.
  12. Un-Wine'd Tour - There’s no better place to “un-wine’d” than in Chesapeake, Virginia. We’ll explore two very unique wineries and enjoy shopping among historic sites you won’t want to miss!


More Things to Do

Fishing Do you like to fish? There's an old adage in...More
Restaurants If a trip to Chesapeake is in your future, prepare...More
History Since the arrival of colonial settlers in 1620,...More