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.

Find Romance in Chesapeake In search of a romantic weekend for two? With gorgeous vistas, amazing antiques, and comfy quarters,... More

Fall Family Adventure Whether you’re looking for hayrides, pumpkin patches, or just some fall foliage, autumn in... More

Into Chesapeake's Outdoors Pack your bags, grab your car keys, buckle up, and take on the open road to experience Chesapeake. More

Great Bridge Battlefield and Waterways Museum in Chesapeake

Exploring Nearby If you're looking for things to do near Chesapeake, VA, consider a day trip! More

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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

Exploring the “Wild” in Chesapeake Home to unspoiled nature and 22 miles of waterways that provide a sanctuary for migratory birds... 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

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Un-Wine'd Tour After breakfast at your hotel, board the bus for a short drive to Historic Williamsburg... More

Find Romance in Chesapeake - With gorgeous vistas, amazing antiques, and comfy quarters, Chesapeake, VA is the ideal place to spend some quality time with the one you love.
Exploring the "Wild" in Chesapeake - Boasting an array of birding and wildlife options that are part of the Virginia Birding and Wildlife Trail - South Chesapeake Loop.
Into Chesapeake's Outdoors - Take on the open road for this WanderLOVE experience!
Exploring Nearby - A great starting point for your next adventure.
Fall Family Adventure - Take the family and see what fall looks like in Chesapeake!
A Culinary Tale - Friendly atmospheres and fresh ingredients are just the beginning of this culinary tale.
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.
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!
Ready, Set, Paddle! - From Lake Drummond to Currituck Sound, enjoy the sights and sounds of the area's unique waterways.
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!