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

You've been to winery wine tasting, but, have you been to a chocolate factory wine tasting? Welcome to our craft chocolate factory to see how chocolate is made while sipping on perfectly paired wine. ... More

Ride along with us as we tour the Monticello Wine Trail and Nelson 151 and the very best wineries, breweries and distilleries in the Virginia wine country. Together we will curate a tour of your preference, stopping in at three ve... 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

Charlottesville, Virginia is the home to some of this nation’s most beloved and historical landmarks with host of the most breathtaking views throughout the Shenandoah Valley. Enjoy a 6-hour guided tour to visit 5 of the most so... More

Escape the city for a sophisticated, full-day retreat into the breathtaking beauty of Loudoun County, Virginia—home to a vibrant wine scene. This approximately 8-hour Vineyard Voyages experience is a curated, stress-free journey... 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

Take this Alexandria Boos and Booze haunted pub crawl tour and add some fun into your work week! This quick but fun tour will take you to four stops for up to two hours. This tour price does not include tastings or tours of the fa... 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

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

Spend one afternoon among Virginia's hidden vineyards - A taste of history! Because every glass of wine you taste here comes from vines rooted in soil once walked by eight Presidents born in Virginia-- George Washington, Thomas J... More

Available only for groups of 6 or more with a phone call. This bike tour is more than just a leisurely ride through scenic landscapes; it's an opportunity to confront our past, understand our present, and shape a more just and equ... More

Embark on an unforgettable Northern Virginia winery tour, led by a certified Sommelier who has extensive knowledge about wines from around the world, and specifically Virginia Wine. The tour will take your group to three excepti... More

Build your wine confidence. No snobs here! White & Red Wine Crafting, Aeration Techniques, Rosé Revelations, Restaurant Etiquette, Molecular Pairing, Chocolate and Wine Pairing made easy!... More

Available only for groups of 6 or more with a phone call. This bike tour is more than just a leisurely ride through scenic landscapes; it's an opportunity to confront our past, understand our present, and shape a more just and equ... More