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

Cycle the gorgeous rural roads of Virginia's wine country. Visit two forward-thinking wineries and eat incredible locally sourced food. Learn about what ecological agriculture means, and walk the vineyards alongside sheep and catt... More

Explore Virginia wine country in comfort and style with your own private chauffeur. This experience is perfect for couples or small groups looking to enjoy the best wineries and breweries around Charlottesville without worrying a... 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

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

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

Discover Virginia Wine Country the way it was meant to be experienced—privately, comfortably, and entirely on your schedule. Skip the crowded buses and cookie-cutter itineraries. This fully private experience is designed exclus... More

Your tours are intentionally designed for small groups, allowing us to provide a level of service and attention that larger tour operators simply cannot match. We take the time to understand your preferences, recommend venues that... More