Guided Wine Experience Tour
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Non-refundable booking. Same price on Viator, Outty earns a commission.
Traveler rating
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Quick answer
Is Guided Wine Experience Tour worth booking?
Guided Wine Experience Tour is a 6-hour experience in Charlottesville, United States, from $675 per person. It scores 35 out of 100 on the Outty Ranking, which we label “Worth a Look”. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 35 / 100
- Rating
- Not yet rated
- Duration
- 6 hours
- From
- $675 per person
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 v
What you get
About this experience
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.
What's included
Included
- Bottled water
- Blue Tooth Speakers
- Chairs, Coolers, and Picnic Blankets
- Snacks
- Ice
What you'll see and do
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.
90 minutes here
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.
90 minutes here
Barboursville Vineyards and Historic Ruins
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
90 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Options you can book
Ford Transit 350 HD
Maximum of 13 travelers Pickup included
Toyota Sienna Platinum Van
Maximum of 4 travelers Pickup included
Chevy Suburban Premier
Maximum of 5 travelers Pickup included
Before you book
- Cancellation
- All sales are final. No refund is available for cancellations.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Andrew's Driving Services
Know before you go
- 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
Photos
Good to know
- Duration
- 6 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $675 to $1000
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 35
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Guided Wine Experience Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Charlottesville.
How much does Guided Wine Experience Tour cost?
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Prices start at $675 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Charlottesville usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Guided Wine Experience Tour take?
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Plan for about 6 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Charlottesville is not rushed.
Is Guided Wine Experience Tour worth it?
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It holds an Outty Ranking of 35 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable food & drink in Charlottesville, and how flexible the cancellation terms are.
Can I cancel or reschedule Guided Wine Experience Tour?
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No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is Guided Wine Experience Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 6-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Guided Wine Experience Tour?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Charlottesville can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Charlottesville and add a light layer if any part of the 6-hour experience runs outdoors or after sunset.
Where does Guided Wine Experience Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Charlottesville within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Charlottesville?
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Charlottesville, VA packs its best experiences into walkable neighborhoods, local food, and day trips nearby. Outty ranks every bookable tour and activity in Charlottesville by rating quality, review depth, booking demand and value, so you can see the standouts before you book. On Outty we rank every Charlottesville experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Virginia Private Custom Wine Tour from Charlottesville, Shenandoah National Park Self-Guided Driving Audio Tour, Private Charlottesville Area Wine Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Charlottesville?
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Spring and fall bring the best weather and lighter crowds in Charlottesville, while summer has the widest choice of tours and evening activities. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Charlottesville?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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