Guided Wine Experience Tour

6 hours Private tour

Guided Wine Experience Tour, photo 2 — Photos: the activity supplier, via Viator

About this activity

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.

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At a glance

Duration: 6 hours
Confirmation: Confirmed within 48 hours
Ticket: Mobile or paper ticket accepted
Group: Your group only
People per booking: 1–15
Guide: English
Operated by: Andrew's Driving Services

What is included

Included

Included: Bottled water
Included: Blue Tooth Speakers
Included: Chairs, Coolers, and Picnic Blankets
Included: Snacks
Included: Ice

Itinerary

Keswick Vineyards

1 h 30 min

Nestled among the rolling hills of Virginia wine country, Keswick Vineyards offers guests a relaxing and scenic escape just outside Charlottesville. As your chauffeur guides you along the beautiful Route 231 corridor, you'll arrive at a historic 400-acre estate surrounded by vineyards, farmland, and stunning views of the Southwest Mountains and Blue Ridge Mountains.

Upon arrival, travelers can stroll through the beautifully landscaped grounds, take in panoramic vineyard views, and settle into the welcoming tasting room or outdoor seating areas. Guests may choose from wine flights, wines by the glass, or bottles to share while learning about the estate's award-winning Virginia wines. The vineyard is family-owned and located on the historic Edgewood Estate, adding both charm and history to the experience.
Southwest Mountain Vineyards

1 h 30 min

Tucked into the rolling countryside of Keswick, Virginia, Southwest Mountains Vineyards offers a refined and relaxing wine-country experience in the heart of the Monticello AVA. As your chauffeur guides you through scenic backroads lined with horse farms, historic estates, and mountain vistas, you'll arrive at a beautiful vineyard estate nestled at the base of the Southwest Mountains. The property combines classic Virginia charm with modern wine hospitality, creating a destination that feels both elegant and welcoming.

Upon arrival, guests are welcomed into a beautifully restored 1903 barn that serves as the winery's tasting room. The historic structure has been thoughtfully renovated while preserving its character, creating a warm atmosphere where visitors can enjoy guided wine tastings, curated flights, and table-side service. Large windows and outdoor seating areas provide sweeping views of vineyards, rolling hills, and the surrounding mountain landscape.
Barboursville Vineyards and Historic Ruins

1 h 30 min

Nestled in the rolling countryside of Orange County, Virginia, Barboursville Vineyards offers one of the most iconic and historic wine experiences in the Commonwealth. As your chauffeur guides you through scenic horse country, vineyards, and picturesque farmland, you'll arrive at a stunning estate that is widely recognized as the birthplace of modern Virginia wine. The property combines award-winning wines, fascinating history, beautiful architecture, and breathtaking views into a truly unforgettable destination.

Upon arrival, guests can enjoy a guided tasting experience featuring some of Virginia's most celebrated wines, including the winery's renowned Octagon blend. Visitors may choose from traditional tastings, premium wine flights, or the exclusive Library 1821 experience, which showcases current and library vintages paired with seasonal culinary offerings. Enthusiasts will appreciate the opportunity to sample wines that have helped establish Virginia as a world-class wine region