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.

Couples Cozy Getaway in Chesapeake

This couples getaway is sure to be a hit with your significant other!...more

Fall Family Adventure

Take the family and see what fall looks like in Chesapeake!...more

A Culinary Tale

Friendly atmospheres and fresh ingredients are just the beginning of this culinary tale....more

Earn Your Scouting Merit Badge

Chesapeake offers many opportunities for scouts to earn merit badges....more

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, which prides itself on its rich history and hosts many significant historic sites and attractions!...more

Birding & Wildlife Viewing - Chesapeake, VA

Birding and wildlife watching is one of the fastest growing hobbies in the country. Bring your group and discover the natural beauty and mystic of Chesapeake, VA. Home to five sites on the Virginia Birding and Wildlife Trail, birders from around the country and overseas, flock to Chesapeake to view long-term and Neotropical migratory songbirds....more

Get Wild!

Get wild with us! This tour takes students through the African desert in search of African elephants and lions. Then cools you off with an educational and fun day on the water in search of bottlenose dolphins and an exclusive behind the scene tour to observe sea turtles from a unique, one-of-a-kind perspective....more

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!...more

Ready, Set, Paddle!

From Lake Drummond to Currituck Sound, enjoy the sights and sounds of the areas unique waterways....more

A Brave New World

Take a journey through history that includes stops at Roanoke Island, Virginia Beach, and Virginia's Historic Triangle - Jamestown, Yorktown, and Colonial Williamsburg....more

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

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