About Us

cider glasses 1175x300

Top Shelf Transportation was started by Roberta Dawn Holliday and Chuck Shipley.

Dawn grew up in Powhatan, Virginia and enjoyed many childhood summers visiting the Blue Ridge Mountains. She spent the first part of her adult life as a stay-at-home mom and home schooling mother of five—an experience she still holds dear to her heart first and foremost. Dawn’s personality has always been well suited for customer service and hospitality. Prior to her founding of Top Shelf Transportation, Dawn enjoyed a career in various management positions.

Chuck has a Structural Engineering degree from NC State and has been designing and building custom homes since 1988 on Lake Gaston. Chuck’s construction business remains successful in both Virginia and North Carolina, but he enjoys his weekends in Charlottesville taking clients in and around the Monticello Wine Trail. Chuck’s gifts and talents have made him one of the most coveted tour guides in the industry.

As with any idea, the initial inspiration for Top Shelf Transportation was followed by a great deal of perspiration, dedication, and plain hard work. Dawn moved full-time to Charlottesville in 2015 to focus her undivided attention on the development and growth of Top Shelf Transportation.

Our goals have been achieved, as we offer Charlottesville, Virginia and our region’s visitors something exceptional, something beyond just a wine or beer excursion. Each tour is a memorable experience, enhanced by our fleet of luxury vehicles and our #TopShelf car, “The Bentley.”

Top Shelf Transportation is the premier, go-to touring company in Charlottesville, Virginia. We cater to both the serious wine connoisseur and to the novice just looking for an enjoyable time. Additionally, we are experts on the brewery trail and the many historical sites in Virginia. We will enhance your experience through our suggestions and expertise.

Our success is based on our dedication to affordable, quality service; Southern hospitality; and our ability to provide our clients with experiences of a lifetime in “The Napa of the East.”

There is no need to choose "Ordinary"when "Extraordinary" is the new option. Choose Top Shelf Transportation!