Ole Crow Tours warmly invites you to explore the very best that Virginia’s renowned wine region has to offer in comfort and style. Simply sit back, relax, and let us handle all the details, carefully ensuring a seamless and unfo... More

With scenic, gently sloping hills leading to one winery after the next—not to mention historic attractions, lavish accommodations, and fine food—Charlottesville, Virginia, is the ideal destination for those seeking a wine-cent... More

This 5-hour, private custom tour features 3 winery visits, luxury Sedan, tasting room recommendations, and an experienced personal Wine Trail guide. Add-on lunch options are available after reserving your tour. Inquire with our te... More

When you book a tour with, you get the leading tour provided within the the Monticello Wine Trail Region. Depending on group size, day of the week, our group can help get you access to some of the best tables at vineyards, guide y... More

We would like to personally invite you to join us on an unforgettable journey through the beautiful countryside of Charlottesville and the surrounding area. As you enjoy tastings of some of Virginia's finest and most celebrated wi... More

If you want to overload your senses, this could be the one. This tour combines two of the area's top vineyards, which not only produce wonderful wine but also provide an unforgettable culinary experience. One of the stops is also ... More