The 15 best things to do in Charlottesville (2026)

The ranked list

1. 

   1. Virginia Private Custom Wine Tour from Charlottesville

   Outty Ranking79

   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 available after reserving your tour. Inquire w. Strongly Recommended at 79/100, 5.0/5 from 660 traveler reviews, 5h from $499.

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2. 

   2. Shenandoah National Park Self-Guided Driving Audio Tour

   Outty Ranking73

   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 snap photos from breathtaking overlooks along Skyline D. Strongly Recommended at 73/100, 4.4/5 from 122 traveler reviews, 4h from $14, free cancellation.

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3. 

   3. Private Charlottesville Area Wine Tour

   Outty Ranking72

   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. Strongly Recommended at 72/100, 5.0/5 from 29 traveler reviews, 5h from $270, free cancellation.

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4. 

   4. Private Wine Tours Transportation from 3 People and More

   Outty Ranking60

   A very comfortable and stylistic a tour and tasting some of Virginia’s finest vineyards and wines. It’s very private and enjoyable for couple looking for an intimate getaway, a small group celebrating a special occasio. Solid Choice at 60/100, 4.4/5 from 28 traveler reviews, 5h from $280, free cancellation.

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5. 

   5. Wine and Culinary Delight Private Tour

   Outty Ranking58

   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 wonderful wine but also provide an unforgettable culinary experience. One of the stop. Worth a Look at 58/100, 4.9/5 from 7 traveler reviews, 5h from $107, free cancellation.

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6. 

   6. 5 Hour Historic Thomas Jefferson Wine Tour

   Outty Ranking56

   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 you enjoy tastings of some of Virginia's finest and most cel. Worth a Look at 56/100, 4.8/5 from 5 traveler reviews, 5h from $111, free cancellation.

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7. 

   7. Charlottesville Challenge Scavenger Hunt

   Outty Ranking56

   Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Aust. Worth a Look at 56/100, 4.0/5 from 2 traveler reviews, 2h from $22, free cancellation.

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8. 

   8. Self Guided Audio Tour Skyline Drive and Shenandoah NP

   Outty Ranking54

   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, revealing the rich history and natur. Worth a Look at 54/100, 3.5/5 from 2 traveler reviews, 4h from $15, free cancellation.

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9. 

   9. Private UNESCO World Heritage Tour

   Outty Ranking54

   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 sites in 1987 for their outstanding cultural signific. Worth a Look at 54/100, 5.0/5 from 2 traveler reviews, 7h from $356, free cancellation.

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10. 

    10. A Spectacular University Hunt: The UVA hunt

    Outty Ranking53

    "Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-t. Worth a Look at 53/100, 3.0/5 from 2 traveler reviews, 1.5h from $15, free cancellation.

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11. 

    11. Custom Wine Tour In Black Suburban With Panoramic Sunroof

    Outty Ranking52

    Discover Virginia Wine Country the way it was meant to be experienced—privately, comfortably, and entirely on your schedule. Skip the crowded buses and cookie-cutter itineraries. This fully private experience is designe. Worth a Look at 52/100, 4.8/5 from 18 traveler reviews, 5h from $549.

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12. 

    12. Shenandoah National Park Self Guided Driving Tour North to South

    Outty Ranking52

    Discover the beauty of Shenandoah National Park with this self-guided GPS audio tour. Take a scenic drive along Skyline Drive, where stunning mountain overlooks and cascading waterfalls await. Explore the park's rich his. Worth a Look at 52/100, 2.1h from $8, free cancellation.

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13. 

    13. A Spectacular Scavenger Hunt in Charlottesville

    Outty Ranking52

    "Dive into adventure, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles,. Worth a Look at 52/100, 1.5h from $15, free cancellation.

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14. 

    14. Special Private Wine Tours, for 2 or 3 people only

    Outty Ranking51

    Keeping Families and Groups and make them happy. Special rides for groups and families like: Surprise Excursion for couples; Concert/Events; welcome/Farewell ride; School groups etc. N/B the rate for this service is per. Worth a Look at 51/100, 4h from $125, free cancellation.

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15. 

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

    Outty Ranking51

    Please join our knowledgeable, entertaining guides in an unparalleled tour of the best of food and culture on the world-famous UVA Corner. Worth a Look at 51/100, 4.6/5 from 5 traveler reviews, 3h from $152, free cancellation.

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