Ole Crow Tours

08/19/2026

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08/16/2026

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At Ole Crow Tours we provide private wine & history tours of the Charlottesville area with a laid back atmosphere.

08/14/2026

As the vineyards begin to glow with the colors of fall, there's no better time to gather your friends and experience Virginia wine country. Picture a crisp afternoon, a glass of wine in hand, and breathtaking views around every bend. Let Ole Crow Tours take you there this season.

We offer both afternoon and evening wine tours, giving you the chance to enjoy Virginia's vineyards in the warm afternoon light or during a beautiful sunset. Whether you're celebrating a special occasion or simply looking for a relaxing day with friends, we'll take care of the driving while you enjoy the journey.

07/04/2026

“We are not merely defending a piece of territory—we are defending the principles that make our country worth fighting for.” – Dwight D. Eisenhower

06/30/2026

Join us for an unforgettable small-group journey through the heart of Tuscany, created for travelers who want to experience Italy slowly, personally, and authentically.

With no more than 6 guests, this inaugural hosted experience is designed around beautiful regional towns, incredible wine and food, meaningful local connections, and the simple joy of sharing Italy together.

As always, Ole Crow Tours takes care of the details so you can relax, settle in, and enjoy the experience as it naturally unfolds.

This is not a rushed sightseeing tour.
It’s Italy the way it’s meant to be experienced.

Visit our website at olecrowtours.com for the full itinerary.

06/25/2026

Summer Sunset Wine Tours Are Back!

Beat the heat this summer and experience Virginia wine country during the coolest and most beautiful time of the day. Our Summer Sunset Wine Tours let you enjoy award-winning wineries, breathtaking vineyard views, and the beauty of the Blue Ridge Mountains as the sun begins to set.

Most tours depart between 2:00–3:00 PM Sunday through Thursday and 3:00–4:00 PM Friday and Saturday, giving you plenty of time to relax and enjoy the evening atmosphere.

As a special summer offer, receive 10% off all Summer Sunset Wine Tours booked Sunday through Thursday.

These seasonal tours are only available for a limited time. Contact Ole Crow Tours today to reserve your Summer Sunset Wine Tour.

01/28/2026

It's been the blind leading the blind over here...but after almost 2 months of single-handedly building a new website, then having to trash it and build another, starting a blog and creating our new Italian Tours, I think I'm ready!
There's still a few things to touch up, but swing by and take a look, and please leave me some feedback!

https://olecrowtours.com

01/10/2026

I've been itching to return to Italy since my family and I visited last spring. After much thought and prayer, Ole Crow Tours is now offering small group Italian tours in the spring of 2026 in addition to tours in the Charlottesville area. Hopefully this is just the beginning of something new for us here at Ole Crow Tours.

To discover more about our tours and services, please click on the link below to visit our newly created website. Our domain is in the process of being transferred, so I apologize for any confusion with the link wording. Additionally, we have launched a blog at astheolecrowflies.com to advertise both our Italy and Charlottesville travels.

https://travefy.com/website/7drw28wrjgfrnnwxgduznn-ywtar32qde4daq2

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 handl...

12/25/2025

"The story of Christmas is the story of God's relentless love for us." —Max Lucado

Merry Christmas from all of us at Ole Crow Tours!!

08/09/2025

Pollak Vineyards has amazing views, but I think this one takes the cake. It's a lonely little picnic table right by the pond, perfect space to get away from everything for a little while.