Looking to Escape...

Discover the perfect blend of relaxation and adventure with Ole Crow Tours. Whether you're craving a serene wine country retreat in Charlottesville or an immersive historic journey through Italy, we customize every detail to create an exclusive, unforgettable experience. Let our expert drivers handle the road while you unwind and explore in comfort, making your getaway effortless and truly exceptional.

Charlottesville Wine & History Tours

Charlottesville blends historic significance with vibrant modern charm. Nestled at the foot of the Blue Ridge Mountains, the city is steeped in American history—from Thomas Jefferson’s Monticello and the University of Virginia’s Jeffersonian architecture to well-preserved Revolutionary and Civil War sites—offering layers of stories around every corner. At the same time, Charlottesville’s wine country has emerged as a premier destination, with rolling vineyards, award-winning wineries, and innovative vintners producing elegant Viognier, bold Cabernet Franc, and nuanced blends. The result is an exceptional escape where world-class wines, scenic landscapes, and deep-rooted history come together to create uniquely memorable experiences.

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Rich in history and natural beauty

Italian Tours

Discover the enchanting beauty of Italy in an intimate, small group setting where every detail is meticulously tailored to delight and amaze you. Our thoughtfully designed small group Italian tours seamlessly blend exceptional personalized service with expertly planned itineraries that take you off the beaten path. With knowledgeable local guides who are passionate about sharing their culture, you will savor authentic regional cuisine, uncover hidden cultural gems, and enjoy a relaxed pacing that allows for genuine connections with the breathtaking places and warmhearted people you meet along the way. Every moment spent in this magnificent country is an opportunity to explore its rich history, vibrant traditions, and stunning landscapes, creating memories that will last a lifetime.

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Travel as a local, not a tourist

Customer reviews

Discover what our clients think about our service

Jeremiah was wonderful to work with, safe driver and pleasant. He took really good care of a group of nine women were in town visiting Charlottesville for a reunion. He helped me plan the winery tour, giving me a great recommendations on a variety of wineries. Would absolutely recommend!

Laura

We knew we wanted a custom tour as we had been to many of the wineries already in this area. Jeremiah spent time really listening to what we wanted and proposed two great custom tour options for us. We landed on blending the two and Jeremiah took care of any reservations we needed. During the tour, two of the wineries recommended another winery that was not on our schedule but Jeremiah happily changed things mid tour to accommodate this winery we really wanted to try! He was friendly and professional the entire time and really went above and beyond to get us the exact tour we wanted. Truly outstanding service! I would wholeheartedly recommend Ole Crow Tours to anyone visiting the Charlottesville area and would definitely use him again the next time we visit! Thank you!

Karen