Top Virginia Wine Tasting Tours

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 about driving or planning. You'll ride in a luxury SUV and visit 2-4 top wineries or breweries such as: King Family Vineyards Pippin Hill Farm & Vineyard Veritas Vineyard & Winery Highlights: -Private SUV (up to 6 guests) -Door-to-door pickup -Custom itinerary -Local knowledgeable driver Duration: 4-6 hours Why Guests Love It: Stress-free experience Flexible schedule Perfect for special occasions Saturday availability is limited and books quickly.

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.

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!

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 moment. On this thoughtfully curated tour, you’ll be enjoying visits to 3 carefully selected wineries located on the scenic eastside of Charlottesville. This journey will take us through the charming Keswick area, once home to Thomas Jefferson’s old stomping grounds, a region rich with history, natural beauty, and timeless elegance.

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 recognized for its architectural design, while the other for its architectural ruins.

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.

With the beauty of the Blue Ridge Mountains surrounding the quaint vineyards of Virginia, this private wine excursion delivers a peaceful and harmonious experience in the great outdoors. A private chauffeur will cruise you and your guests from historic Charlottesville to the countryside. Spend the day touring the area and sampling wines from multiple wineries. On the Wine Trail, you’ll have your choice of which tasting rooms to visit and when to have a picnic lunch.

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 Thomas Jefferson’s lasting influence on the region. This experience promises to be both relaxing and enlightening, blending the natural beauty, exquisite flavors, and historical depth unique to this area.

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 exclusively for your group, allowing you to explore Charlottesville's renowned wineries, breweries, cideries, and distilleries at your own pace while traveling in a luxury Chevrolet Suburban featuring a panoramic sunroof. Whether you're celebrating a special occasion, planning a romantic getaway, reconnecting with friends, or simply looking to experience the best of Virginia wine country, our local concierge team helps create a seamless day from start to finish. 100% Private Tour — No strangers, no shared transportation, no fixed schedule. Customized Itinerary — Visit the wineries, breweries, cideries, & tasting rooms that match your group's preferences. Local Expertise — Our team knows the region's hidden gems, iconic vineyards, and reservation-only experiences.

Experience the ultimate Food & Wine education retreat in the gorgeous Blue Ridge Mountains about an hour west of Washington D.C. This 2-day Blue Ridge Wine Retreat delves into 6 wine and food experiential classes, an evening farm-to-table dinner filled with laughter, learning and fun. We finish with our famous Choco-Vino Challenge final exam.

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 facilities. This tour will take you to a total of four watering holes in Alexandria, which may be a combination of craft producers in Alexandria, and local bars. There will be a variety of haunted stops in between these already notorious bars and pubs! We'll spend about 15-20 minutes to one hour at each destination. Exact lineup depends on day of week and season. Drinks are not included. The total duration is approximately 1 hour and 45 minutes. The duration of the tour includes, drinks at the establishments, history and story telling at the historic sites and walking to and from the historic sites.

The Ghost Tour is Williamsburg's first and only murder-focused tour. Explore areas that other history tours would be afraid to visit. Explore a historic city that conceals a sinister and unsettling past. A netherworld of horrific death and hatred. Accompany your guide on foot to some of our favorite local watering establishments. To help you get ready for what's to come, try a drink with a murder theme or one of the pub's specialty beverages. Then, take a stroll through the dim, peaceful streets of Historic Williamsburg, where you may learn the real stories of the city's most notorious crimes. There's nothing ghostly about Williamsburg's scariest tour. It has to do with murder.

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 fit your group's personality, and create an itinerary tailored to your occasion. Whether you're celebrating a birthday, anniversary, bachelorette party, date day, or simply enjoying time with friends, every experience is customized around you. What truly makes us different is your concierge-style approach. From the moment we pick you up until we safely return you home, we're focused on the details. We coordinate timing between venues, help keep your day running smoothly, offer local knowledge of Virginia wine country, and provide the flexibility to adjust the day as needed.

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 exceptional wineries in the region. Relax in a comfortable private vehicle as you explore the picturesque landscapes of the serene Virginia countryside. Enjoy expertly guided tastings, behind-the-scenes experiences, and personalized service tailored to your preferences. Whether you're celebrating a special occasion or simply indulging in a luxurious day of wine exploration, our curated tours offer an unparalleled experience. Discover the finest wines Northern Virginia has to offer with a unique, VIP experience!