Trip Ideas

Itineraries for Chesapeake Vacations

One region, many destinations, unlimited experiences!

Chesapeake is the heartbeat of Coastal Virginia and boasts a rich cultural history, scenic natural wonders, delicious dining, and abundant shopping. From couples’ getaways at secluded campgrounds to noshing along the foodie trail, there are so many things to do in Chesapeake, VA. 

Experience the seasons

Spring in Chesapeake means delightful weather and strawberry season! Many local farms feature pick-your-own strawberry fields with plenty more to see. 

If you’re more of a peach fan, then you’ll want to visit during the summer. July and August are prime peach season, and you’ll find the farms in Virginia bursting with them, ready for picking. 

If you and the family are visiting during the fall, we’ve got the itinerary for you! Choose from hayrides, pumpkin patches, or exploring our parks to take in the fall foliage. Autumn in Chesapeake is sure to delight family members of all ages.

Don’t forget to join us for the holidays when the lights glitter and the hot cocoa hits just right. Best of all, Chesapeake has plenty of indoor fun to stay out of the cold.

Explore the City

There’s nothing like a road trip to get a dose of true Chesapeake southern hospitality on-the-go, so pack your bags, grab your car keys, and take on the open road. While exploring the city you will find unique shopping experiences, including antique shops, chic boutiques, and more. 

And when it comes to eating and drinking, Chesapeake has it all—scrumptious breakfast options, exceptional seafood, and classic comfort foods. 

They say Virginia is for lovers and Chesapeake is no exception. With gorgeous views, amazing food, and comfy quarters, Chesapeake is the ideal place to spend some quality time with the one you love. 

Take A Look at the Wildlife

Birding and wildlife viewing in Chesapeake, VA is kind of a big deal. With 213 species of birds nesting here each spring, it becomes a sanctuary for the birds and people who love to watch them. Home to unspoiled nature and 22 miles of waterways, nature-lovers will feel right at home here. 

Explore Nearby

From the mysterious Roanoke Island to historic Williamsburg, history is all around Chesapeake. If you’re looking for a day trip, Chesapeake is the perfect home base when visiting these and other major historical sites nearby.

Whether you’re visiting alone, with a loved one, or the whole family, a trip to Chesapeake is sure to be a trip you’ll never forget. Join us and let the moments begin.


Chesapeake Itineraries List

More Things to Do

Restaurants Discover renowned local restaurants in Chesapeake,...More
History From historic trails to museums, learn about...More
Shopping With a wide spectrum of shops, services and...More