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.

A Culinary Tale For foodies on the hunt for everything from foie gras to French fries, Chesapeake has you covered.... More
Exploring Nearby If you're looking for things to do near Chesapeake, VA, consider a day trip! More
Exploring the “Wild” in Chesapeake Home to unspoiled nature and 22 miles of waterways that provide a sanctuary for migratory birds... More
Fall Family Adventure Whether you’re looking for hayrides, pumpkin patches, or just some fall foliage, autumn in... More
Find Romance in Chesapeake In search of a romantic weekend for two? With gorgeous vistas, amazing antiques, and comfy quarters,... More
Into Chesapeake's Outdoors Pack your bags, grab your car keys, buckle up, and take on the open road to experience Chesapeake. More
Pickin Peaches Although the height of peach season is typically July and August, you can start eating these fuzzy,... More
Ready, Set, Paddle! Enjoy a hearty breakfast at Cracker Barrel Restaurant before heading out to one of the only two... More
Shop 'til You Drop! Enjoy breakfast at your hotel then head down to Historic Williamsburg to the Prime Outlets. ... More
Spring Into Chesapeake Hike, fish, stroll, and paddle, all while flowers around you bloom. With mild temperatures, stunning... More
Strawberry Fields For Everyone Whether you’re in search of tiny delicate berries or gargantuan juice-explosions, you’ll... More
Winter Fun in Chesapeake Whether you’re in town to see Santa or you’re seeking to explore the twinkling lights of... More

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