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 unforgettable experience for you and your guests to truly savor every...

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 wines, you will be completely immersed in the rich history shaped by...

Turn a day in Virginia wine country into a seamless experience. Our private wine & beer tours are designed for couples, small groups and anyone looking to enjoy the best of the Monticello Wine Trail without worrying about driving, planning or logistics. Whether you're celebrating a birthday,...

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 cattle, with your sommelier-guide.

Purchase one tour per car, not per person. Everyone listens together! Take a scenic drive through Virginia’s verdant wilderness with this self-guided tour. Stop to snap photos from breathtaking overlooks along Skyline Drive. Hike portions of the famous Appalachian Trail. Find out how this wild,...

A very comfortable and stylistic a tour and tasting some of Virginia’s finest vineyards and wines. It’s very private and enjoyable for couple looking for an intimate getaway, a small group celebrating a special occasion, a bridal party, or a business team looking for a change of scene. You are...

Discover the beauty of Skyline Drive, a stunning 100-mile stretch through Shenandoah National Park. This self-guided audio experience transforms your drive into an engaging journey, revealing the rich history and natural wonders of the Blue Ridge Mountains. Encounter sweeping overlooks, hidden...

This exceptional tour takes us to two of Thomas Jefferson's most iconic masterpieces, the University of Virginia and Monticello, both honored as UNESCO World Heritage sites in 1987 for their outstanding cultural significance. Our journey begins with a detailed guided tour of the picturesque...

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re...

Charlottesville has experienced its fair share of turmoil and tragedy, alongside its charming streets and delectable cuisine. From the legend of the enigmatic Moon Ghost who terrorized a local family to the brooding figure of James Madison reported at his beloved Montpelier, the Charlottesville...

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 team to learn more, after reserving, to learn about food options and...

The Downtown Mall Food Tour is a unique and memorable way to visit one of America's top college towns.