The 15 best things to do in Charlottesville (November 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 666 traveler reviews, 5h from $499.

   See prices and availability
2. 

   2. Shenandoah National Park Self-Guided Driving Audio Tour

   Outty Ranking75

   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 75/100, 4.5/5 from 125 traveler reviews, 4h from $17, free cancellation.

   See prices and availability
3. 

   3. Private Charlottesville Area Wine Tour

   Outty Ranking73

   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 73/100, 5.0/5 from 30 traveler reviews, 5h from $270, free cancellation.

   See prices and availability
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.

   See prices and availability
5. 

   5. Wine and Culinary Delight Private Tour

   Outty Ranking59

   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 59/100, 4.9/5 from 7 traveler reviews, 5h from $248, free cancellation.

   See prices and availability
6. 

   6. 5 Hour Historic Thomas Jefferson Wine Tour

   Outty Ranking57

   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 57/100, 4.8/5 from 5 traveler reviews, 5h from $270, free cancellation.

   See prices and availability
7. 

   7. Charlottesville Challenge Scavenger Hunt

   Outty Ranking57

   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 57/100, 4.0/5 from 2 traveler reviews, 2h from $22, free cancellation.

   See prices and availability
8. 

   8. Private UNESCO World Heritage Tour

   Outty Ranking57

   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 57/100, 5.0/5 from 3 traveler reviews, 7h from $356, free cancellation.

   See prices and availability
9. 

   9. Chains, Coffins, & Curses: Charlottesville Ghost Tours

   Outty Ranking56

   Charlottesville has experienced its fair share of turmoil and tragedy, alongside its charming streets and delectable cuisine. From the legend of the enigmatic Moon Ghost who terrorized a local family to the brooding figu. Worth a Look at 56/100, 3.8/5 from 29 traveler reviews, 1h from $26, free cancellation.

   See prices and availability
10. 

    10. Self Guided Audio Tour Skyline Drive and Shenandoah NP

    Outty Ranking55

    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 55/100, 3.5/5 from 2 traveler reviews, 4h from $15, free cancellation.

    See prices and availability
11. 

    11. Crozet Virginia Winery and Bike Tour Experience

    Outty Ranking55

    Cycle the gorgeous rural roads of Virginia's wine country. Visit two forward-thinking wineries and eat incredible locally sourced food. Learn about what ecological agriculture means, and walk the vineyards alongside shee. Worth a Look at 55/100, 5.0/5 from 2 traveler reviews, 6h from $220, free cancellation.

    See prices and availability
12. 

    12. A Spectacular University Hunt: The UVA hunt

    Outty Ranking54

    "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 54/100, 3.3/5 from 3 traveler reviews, 1.5h from $15, free cancellation.

    See prices and availability
13. 

    13. A Spectacular Scavenger Hunt in Charlottesville

    Outty Ranking53

    "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 53/100, 1.5h from $15, free cancellation.

    See prices and availability
14. 

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

    Outty Ranking53

    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 53/100, 2.1h from $8, free cancellation.

    See prices and availability
15. 

    15. Custom Wine Tour In Black Suburban With Panoramic Sunroof

    Outty Ranking53

    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 53/100, 4.8/5 from 19 traveler reviews, 5h from $549.

    See prices and availability

Traveler ratings are provided by Viator and Tripadvisor. The Outty Ranking is our own independent evaluation. How the ranking works.

Frequently asked questions