




Available languages
6 hours
Mobile ticket
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.
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
Keswick Vineyards
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
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.
Maximum of 5 travelers Pickup included
Maximum of 4 travelers Pickup included
Maximum of 13 travelers Pickup included
Bottled water
Blue Tooth Speakers
Chairs, Coolers, and Picnic Blankets
Snacks
Ice
Select a pickup point
All sales are final. No refund is available for cancellations.
Operated by Andrew's Driving Services