About Us

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Top Shelf Transportion staffTop Shelf Transportation was started by Roberta Dawn Holliday and Chuck Shipley. Dawn spent the first part of her adult life as a Mother, which is a job that comes first and foremost to her still, but she has always been well suited for customer service and, until starting this venture, has spent her career in management in some form or another. Her last position before starting Top Shelf was as Manager of Shipley Builders, Inc. Chuck is a general contractor who has built quite a successful construction business in Virginia as well as in North Carolina. Chuck and Dawn are both wine enthusiasts who started coming to Charlottesville several years ago to partake of the numerous wineries in the area.

Charlottesville is centrally located in the Monticello Wine Trail, an area fast becoming known as the “Napa of the East” because the best wine in state is being made right here in the shadow of Mr. Jefferson’s mountain home (Monticello) and close to his vision of an “Academic Village” (the University of Virginia). Needless to say, Dawn and Chuck fell in love with the area, and in no time at all Dawn began dreaming about starting a wine tour company. As with any idea, the initial inspiration was followed by a great deal of perspiration, dedication and plain hard work. Dawn’s research eventually led her to cross paths with Bit Pressley, an experienced wine trail guide who is also a really geeky history guy with a degree in American History and American Political thought. Bit has been to over 160 wineries throughout Virginia, knows all the wine owners and winemakers on the Monticello Trail and has become a part of the local wine culture.

Together, the three created Top Shelf Transportation, which is the premier go-to touring company in Charlottesville for both the serious wine connoisseur or the novice just looking to have a good time on the trail. Additionally, we are no strangers to the brewery trail and/or the many historical sites in Virginia. Our success comes from our dedication to quality service and our ability to provide our clients with experiences of a lifetime.