Private Charlottesville Area Wine Tour

4.9

Reviews

Recommended by 100% travellers

100% of guests rated this experience 4 stars or higher

4.9 (30)

Recommended by 100% travellers

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Show all photos

4.9

Reviews

Recommended by 100% travellers

100% of guests rated this experience 4 stars or higher

4.9 (30)

Recommended by 100% travellers

Earliest Date Available: October 25, 2026This experience is in high demand. Book now to lock in the next available date.

Free CancellationCancel for free up to 1 day before your experience

Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world

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Japan's #1 food travel platform

Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT

Location

Albemarle

Duration

5 hours

Group size

Max 6 guests

Accessibility

Stroller Accessible

Language

English

Location

Albemarle

Duration

5 hours

Group size

Max 6 guests

Accessibility

Stroller Accessible

Language

English

Why travelers loved this

4.9

•30 reviews

US$285.96 per guest

Instant Confirmation

Guest

Adult x2

Date

Add dates

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Earliest Date Available: October 25, 2026This experience is in high demand. Book now to lock in the next available date.

Free CancellationCancel for free up to 1 day before your experience

Food for HappinessFor every guest in your booking, we donate 10 meals to children around the world

Why book with byFood?

Japan's #1 food travel platform

Trusted by 50,000+ travelers worldwideCurated by food lovers, for food loversFeatured in CNN, Forbes & NYT

Description

Good to Know

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.

Private transportation

Water Bottles

Knowledgeable and Friendly Guide

In-vehicle air conditioning

Air-conditioned vehicle

All food and beverages

1 hour 40 minutes · Admission Ticket Free

Merrie Mill Farm and Vineyard

Merrie Mill Farm & Vineyard is a tasting room destination in Keswick, VA. Founded by Guy and Elizabeth Pelly, Merrie Mill reimagines the tasting room experience by marrying a devotion to warm, approachable hospitality with a weird, wonderful setting that delights and inspires.

Merrie Mill Farm & Vineyard is a tasting room destination in Keswick, VA. Founded by Guy and Elizabe…

1 hour 40 minutes · Admission Ticket Free

Barboursville Vineyards and Historic Ruins

The entire estate is open for tasting our wines in a stroll or in a picnic, and our informed and enthusiastic hosts present tastings continuously in the Discovery Tasting Room, every day of the week, as well as in Library 1821, . The Tasting Room is where the broadest range of our current vintages is introduced, while the Library 1821 presents a changing selection of flights of current and older vintages from our cellars, and with seasonal culinary pairings designed by our chefs. Every encouragement is given, also, to enjoying our wines in the truly splendid lawns surrounding the historic Landmark Ruins of Thomas Jefferson's mansion for Governor James Barbour, a pleasant stroll away.

The entire estate is open for tasting our wines in a stroll or in a picnic, and our informed and ent…

1 hour 40 minutes · Admission Ticket Free

Southwest Mountains Vineyards

Thoughtfully crafted by our skilled and renowned winemaking team, each wine showcases the extraordinary terroir of Virginia’s Monticello AVA. For that perfect glass or beautiful bottle to celebrate special occasions, Southwest Mountains Vineyards wine will be a wonderful addition to any day.

Thoughtfully crafted by our skilled and renowned winemaking team, each wine showcases the extraordin…

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Pickup Details

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Free cancellation

Cancel up to 1 day before for a full refund.

No refund within 1 day of the experience or no-shows.

4.9

30 reviews

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30 reviews

CltlkbOctober 2026 • TripAdvisor

Great day

We had a great day with Keith. We liked the 3 different wineries-different vibes, lots of different styles of wine. Our favorite was Barboursville. Also went to Merrie Hill and Southwest Mountain. The day was very relaxing since we were not driving through the remote areas on the narrow, winding roads.

Chris_SJuly 2026 • Viator

An Enjoyable Afternoon Made Possible by Ole Crow Tours

Ole Crow Tours makes wine touring convenient and easy to schedule. Let me explain: Our group of 4 were staying at a B&B in Orange - a location not normally on their list for tour pickups but when asked via email if they could manage this, within moments they replied back that they would indeed pick us up at this location with no additional charge. Fast and easy. When the day of our scheduled tour arrived, Keith our driver for the afternoon, was super prompt and out of the van ready to ass...read more

Response from ViatorJuly 10, 2026

Thank you so much for your kind words; that was amazing! I wish I had the pleasure of driving you all myself for your tour, but I'm thankful Keith did a good job. I'm thrilled that you had a wonderful day, and we hope to see you all again sometime.

Noel_SMay 2026 • Viator

Great experience. ...

Great experience. Visited some excellent spots. Ride was clean and comfortable. Will go back and do it again one day

RebekaluMay 2026 • TripAdvisor

Wine tasting and so much more!

We toured local vineyards for two days with Jeremiah. He arrived promptly each day in a very comfortable van. We enjoyed the information he provided regarding the area and vineyards as we traveled. The vineyards were diverse and the wines provided great variety with something for everyone. The views from the vineyards provided an unexpected bonus! Thanks Jeremiah!

Texas_Guy57March 2026 • TripAdvisor

Knowledgeable & Experienced… Perfect!

Excellent tour! We visited four wineries with a focus on white wines. Jeremiah was very accommodating and offered good insights on the history of the region as well as some of the wineries we visited. He was always waiting which gave us flexibility to adjust our timing as the day progressed. Highly recommend for a comfortable and safe experience through the wine country!