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Top Charlottesville Private Sightseeing Tours

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Charlottesville Tours

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Shenandoah National Park Self-Guided Driving Audio Tour

Purchase one tour per car, not per person. Everyone listens together! Take a scenic drive through Virginia’s verdant wilderness with this self-guided tour. Stop to …More

4.6 (115)

Shenandoah National Park Self-Guided Driving Audio Tour

Purchase one tour per car, not per person. Everyone listens together! Take a scenic drive through Virginia’s verdant wilderness with this self-guided tour. Stop to...

4 to 5 hours • Free Cancellation
4.6 (115)
from
$14
Virginia Private Custom Wine Tour from Charlottesville

This 5-hour, private custom tour features 3 winery visits, luxury Sedan, tasting room recommendations, and an experienced personal Wine Trail guide. Add-on lunch options are …More

5.0 (659)

Virginia Private Custom Wine Tour from Charlottesville

This 5-hour, private custom tour features 3 winery visits, luxury Sedan, tasting room recommendations, and an experienced personal Wine Trail guide. Add-on lunch options are...

5 hours • Hotel pickup offered
5.0 (659)
from
$499
Private Charlottesville Area Wine Tour

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 …More

4.8 (30)

Private Charlottesville Area Wine Tour

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...

5 hours • Hotel pickup offered • Free Cancellation
4.8 (30)
from
$111
Self Guided Audio Tour Skyline Drive and Shenandoah NP

Discover the beauty of Skyline Drive, a stunning 100-mile stretch through Shenandoah National Park. This self-guided audio experience transforms your drive into an engaging journey, …More

4.0 (3)

Self Guided Audio Tour Skyline Drive and Shenandoah NP

Discover the beauty of Skyline Drive, a stunning 100-mile stretch through Shenandoah National Park. This self-guided audio experience transforms your drive into an engaging journey,...

4 to 5 hours • Free Cancellation
4.0 (3)
from
$15
Wine and Culinary Delight Private Tour

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 …More

4.9 (7)

Wine and Culinary Delight Private Tour

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...

5 hours • Hotel pickup offered • Free Cancellation
4.9 (7)
from
$107
5 Hour Historic Thomas Jefferson Wine Tour

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 …More

4.8 (5)

5 Hour Historic Thomas Jefferson Wine Tour

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...

5 hours • Hotel pickup offered • Free Cancellation
4.8 (5)
from
$111
The UVA Corner Food Tour: Private Walking Food Tour in Charlottesville

Please join our knowledgeable, entertaining guides in an unparalleled tour of the best of food and culture on the world-famous UVA Corner. …More

4.6 (5)

The UVA Corner Food Tour: Private Walking Food Tour in Charlottesville

Please join our knowledgeable, entertaining guides in an unparalleled tour of the best of food and culture on the world-famous UVA Corner....

3 hours • Free Cancellation
4.6 (5)
from
$152
Private UNESCO World Heritage Tour

This exceptional tour takes us to two of Thomas Jefferson's most iconic masterpieces, the University of Virginia and Monticello, both honored as UNESCO World Heritage …More

5.0 (2)

Private UNESCO World Heritage Tour

This exceptional tour takes us to two of Thomas Jefferson's most iconic masterpieces, the University of Virginia and Monticello, both honored as UNESCO World Heritage...

7 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$156
Private Custom Charlottesville Wine or Beer Tours

Turn a day in Virginia wine country into a seamless experience. Our private wine & beer tours are designed for couples, small groups and anyone …More

3.9 (7)

Private Custom Charlottesville Wine or Beer Tours

Turn a day in Virginia wine country into a seamless experience. Our private wine & beer tours are designed for couples, small groups and anyone...

6 hours • Hotel pickup offered • Free Cancellation
3.9 (7)
from
$489

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Excellent Experience
New York City
Virginia Private Custom Wine Tour from Charlottesville
C7503LKemilyw, Sep 2026
Excellent Experience
Such a sweet driver that was kind and maintained a very clean car. He took us to 3 different wineries that were all gorgeous. The first had my favorite wine, the second had great food, and the third had the photo opps I was looking for. Maintaining time and consideration for us, the driver exceeded expectation. I would highly recommend this tour!
Read more
The app was great. I was...
New York City
Shenandoah National Park Self-Guided Driving Audio Tour
Donald_M, Sep 2026
The app was great. I was...
The app was great. I was concerned about whether or not I would be able to get it to work at an entry location that was not an option in the app. It will work wherever yo decide to start your drive. Just be sure to get the app installed before taking your trip. I connected phone to car radio via Bluetooth and opened app once I arrived at my entry point and everything worked beautifully. GPS found my location and from there all I had to do was drive. The direction ( north or south didn't matter) just select Start Touring in the app, leave it open and begain your drive. The app audio guide will do the rest.
Read more
Perfect experience
New York City
Virginia Private Custom Wine Tour from Charlottesville
Compass19660208792, Sep 2026
Perfect experience
Roger was an amazing driver. Professional, polite, and a wonderful gentleman!
Read more
Bday tour with the bestie!
New York City
Wine and Culinary Delight Private Tour
apayne87, Sep 2026
Bday tour with the bestie!
Loved Danielle! She was so fun and sweet. Two very different winery’s, both nice. Short walk to ruins and beautiful at Barboursville Vineyards, and we were able to bring our wine for the walk. Love the prix fixe curations at early mountain. Bison was soooooo good!
Read more
Great guide!
New York City
Shenandoah National Park Self-Guided Driving Audio Tour
simgedave, Sep 2026
Great guide!
We absolutely loved this guide so much so that we will buy another guide for another destination.One issue we faced was not being able to increase the volume. Even though the phone volume was at max and we tried adjusting the car volume, it was just not getting any louder. It was fine for the most part, but if my kids were a bit older, they might have complained that they couldn't hear the guide in the backseat of the car.The guide itself was very helpful and entertaining and made our trip much more enjoyable.
Read more
Awesome car service!
New York City
Private Custom Charlottesville Wine or Beer Tours
Callie_P, Aug 2026
Awesome car service!
Thank you sooo much to Melissa!! She was on time, friendly and professional! She also gave us recommendations on wineries which was so helpful!! We would definitely book again!
Read more
Kathleen was so...
New York City
Private UNESCO World Heritage Tour
Martha_W, Aug 2026
Kathleen was so...
Kathleen was so incredibly knowledgeable and adaptable. I was traveling with my 10 year old grandson who is quiet but totally soaked everything in. We were so fortunate to have such flexibility as we were the only two on our trip. Definitely so worthwhile.
Read more
An Enjoyable Afternoon Made Possible by Ole Crow Tours
New York City
Private Charlottesville Area Wine Tour
Chris_S, Jul 2026
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 assist us get comfortable on our way to the 1st of 3 destinations.Reservations had already been made by Ole Crow Tours at all 3 of our winery destinations so no wait, no fuss - just prompt seating and enjoyable tastings pared with food at all 3 stops. (Food and wine are not included in the cost of the private tour so be sure to bring payment for those items that you'll consume.)Ole Crow Tours scheduled us to visit 3 wineries during our 5 hour tour which covered a range of venues and styles. Each stop offered its own vibe and unique character and each showcased the splendid wines and hospitality of Virginia's premier wine country.We appreciate the professionalism of Ole Crow Tours throughout the planning and execution phases of our trip. We would recommend them to anyone interested in winery tours without the risk of drinking and driving. This is the way to go.
Read more
Great trip
New York City
Private Custom Charlottesville Wine or Beer Tours
Lisa_S, Jul 2026
Great trip
Very professional, take you anywhere you wanna go also offer great recommendations. Went with three couples everybody had a very good time.
Read more
Excellent way to tour Skyline Drive. It's like having a tour guide with you.
New York City
Self Guided Audio Tour Skyline Drive and Shenandoah NP
lindaaM1076NK, Jul 2026
Excellent way to tour Skyline Drive. It's like having a tour guide with you.
This was a wonderful way to get an overview of the park. I used the app via CarPlay in my car, and the app knew our location via GPS. It was very informative, and well worth the cost. I would certainly do this again in our next National Park visit.I had not received the code via email to start the app, but I was able to resolve the issue with a 5 minute phone call, so all was well. Make sure to download the tour contents before entering the park. We did it before leaving the hotel wifi.Unfortunately, the weather was cloudy/overcast so we could not always observe the features described -- but at least we had the description from the audio tour. We jumped off the tour to explore Luray Caverns, then returned to resume the tour. It is a long tour, since the speed limit is only 35. We ended up cutting the tour short to drive on towards Gettysburg for our next stop on the trip.
Read more
Skyline Drive and Shenandoah National Park
New York City
Self Guided Audio Tour Skyline Drive and Shenandoah NP
Carliene A, May 2026
Skyline Drive and Shenandoah National Park
We had a terrific time, which was 100% enhanced by the audio narrative; interesting and informative. It was cloudy one day so we went back on a sunny and was able to use the narrative both days. Highly recommended
Read more
Great experience. ...
New York City
Private Charlottesville Area Wine Tour
Noel_S, May 2026
Great experience. ...
Great experience. Visited some excellent spots. Ride was clean and comfortable. Will go back and do it again one day
Read more
Top Notch Tour
New York City
5 Hour Historic Thomas Jefferson Wine Tour
Jewel_C, May 2026
Top Notch Tour
My husband and decided to take a long weekend and do a wine tour. We both like history and so we chose the Historic Thomas Jefferson wine tour. It was lovely! Keith was our driver and he was friendly and professional and a great driver. The owner, Jeremiah, was communicative beforehand to make sure I knew what to expect and how to identify our driver, etc. Seems like a great tour company and I would highly recommend Old Crowe Tours and this wine tour.
Read more
Thomas Jefferson wine tour
New York City
5 Hour Historic Thomas Jefferson Wine Tour
808StephanieR, Nov 2025
Thomas Jefferson wine tour
Great tour, Jeremiah was very accommodating and gave us plenty of time at each stop. He made sure we were all set at each winery so we could bypass the crowds.
Read more
Extremely custom tour. Excellent experience. Great customer service.
New York City
Wine and Culinary Delight Private Tour
535JanetK, Oct 2025
Extremely custom tour. Excellent experience. Great customer service.
Jeremiah planned the perfect day for my family of six to enjoy a personalized food and wine tour visiting the three vineyards that we wanted to see. Because two of the vineyards were close to the house we were renting he arranged for our driver, Minette, to pick us up at the house and drop us off there. It was the perfect day. Monette was a great driver with a fun , sweet, outgoing, personality. She was awesome. The Infinity SUV she drove was large enough for all six adults to fit very comfortably. Ole Crow Tours went out of their way to make sure that the day worked perfectly for us - even scheduling a stop by the house midday so we could let our pup out for a few minutes before heading back out on the rest of the tour. They were so accommodating. I highly recommend this company if you would like to schedule a private custom tour of any wineries in the Charlottesville area.
Read more
Graciously accommodating.
New York City
Private UNESCO World Heritage Tour
thomasandteresad, Aug 2025
Graciously accommodating.
Jeremiah arrived on time to pick us up in a clean and comfortable vehicle. He was very professional, polite and knowledgeable. We wanted to visit a special location that wasn’t on the itinerary and he graciously accommodated us. Thank you Jeremiah for your kindness.
Read more
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