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01Four days of travel by coach — Great Smoky Mountains, Shenandoah National Park, and the Titanic Museum in Pigeon Forge, with bilingual guides and meals included.
02Three hours cycling on rural roads — visit two wineries, enjoy locally sourced food, and learn about ecological agriculture with a sommelier-guide.
03Two to three hours of app-led exploration — tackle trivia and puzzles while uncovering landmark highlights in Charlottesville with friends or colleagues.
04A downloadable audio tour for Eastern USA covering 14 iconic destinations — explore at your own pace without needing cell service.
05Convenient private transfer to Charlottesville Airport, available 24/7, using either a luxury sedan or a 6-passenger SUV.
06Four hours of transport and group activities — pickup from your location, then enjoy music, games, or social events tailored for families or groups.
07Luxury SUV transfers between Charlottesville Albemarle Airport and local destinations, including real-time flight monitoring and meet-and-greet service available.
08Tailored wine tour in a spacious black suburban with a panoramic sunroof, highlighting the Monticello Wine Trail region's best vineyards and dining options.
“I had an excellent experience on the Monticello wine tour. They assisted in creating a personalized itinerary and provided fantastic suggestions based on what I wanted for the day. Our driver, Mark, was friendly and very informed about the region. I would definitely recommend them for a laid-back visit.”— 463reannac
09Visit two top vineyards in Charlottesville on this private tour, featuring wine tastings and a culinary experience at each location.
“Jeremiah designed an ideal food and wine tour for my family of six, including visits to three specific vineyards. He arranged for our driver, Minette, to pick us up and drop us off at our rental house, making it a hassle-free experience. Minette was an excellent driver with a friendly and cheerful personality, which added to our enjoyment. The Infinity SUV provided plenty of space for all six of us to ride comfortably. Ole Crow Tours was incredibly accommodating, even planning a stop at our house so we could let our dog out briefly before continuing the tour. I strongly recommend this company for anyone wanting a private, tailored winery experience in the Charlottesville area.”— 535JanetK
10Four to six hours in a private SUV — visit 2 to 4 wineries or breweries with a custom itinerary and local driver.
“Our winery tour with Melissa was outstanding. Everything flowed smoothly from beginning to end. She was punctual, which established a professional atmosphere, and she adapted easily as our itinerary changed throughout the day.”— Reia_C
11Private transfer from Charlottesville International Airport to your destination, with 24-hour availability and options for Luxury Sedan (3 passengers) or SUV (6 passengers).
“Terri maintained an upbeat and cheerful demeanor even past midnight. The ride was quite enjoyable, and I'm thankful to have had the opportunity to work with such a professional and pleasant individual.”— Hannah_Y
12Four hours of guided exploration — the University of Virginia and Monticello, both UNESCO World Heritage sites, with time for refreshments at the Monticello Cafe.
“Jeremiah picked us up right on time in a clean, comfortable vehicle. He was professional, polite, and knowledgeable. When we asked to visit a special spot not included in the itinerary, he kindly made it happen. Thank you, Jeremiah, for your generosity.”— thomasandteresad
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Listicle · top 10Featuring Four-day Smoky Mountain tour from New York City, Winery and bike tour in Virginia wine country, and 10 more.
Listicle · top 10Featuring Four-day Smoky Mountain tour from New York City, Self-guided audio tour bundle for Eastern USA road trips, and 9 more.
Listicle · top 10Featuring Four-day Smoky Mountain tour from New York City, Private airport transfer to Charlottesville International Airport, and 10 more.
Looking for landmarks instead? See the top places to visit in Charlottesville.
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