Charlottesville isn’t just about Virginia’s charming streets and wineries; it’s a place where history, scenery, and unique experiences collide. Whether you’re savoring a private wine tour with a personal guide or exploring the darker side of town’s past on a ghost walk, this city offers something for every type of traveler. I particularly enjoy how some tours combine natural beauty with rich stories—like tasting Virginia wines amid the Blue Ridge backdrop or strolling past Jefferson’s historic landmarks. With so many options, you’ll want to pick your experiences based on your interests, budget, and how much time you have.
Charlottesville is famous for its vineyards, historic sites, and lively food scene, but it also offers immersive activities like scavenger hunts and ghost tours. We’ve compiled a list of the best tours in town, covering everything from wine tastings to historical explorations, so you can plan your ideal trip with confidence.
Quick Overview of Charlottesville Tours
Our list features wine tours—including private, custom, and group options—ghost walks, and even food tours along the Downtown Mall. For history lovers, full-day Jefferson-focused trips and UNESCO heritage site visits provide rich insights. For fun and interactive experiences, check out the scavenger hunts and self-guided tours. Now, let’s explore each of these fantastic options.
1. Virginia Private Custom Wine Tour from Charlottesville
At number 1, this private wine tour offers a flexible, personalized way to explore Virginia’s renowned Blue Ridge Mountain vineyards. Your own chauffeur guides you through 3 to 4 wineries, with the option to choose your stops or let your guide recommend hidden gems. The tour includes tastings, bottled water, and even a picnic lunch if you like—perfect for couples celebrating or small groups wanting a relaxed day out. With a five-star rating based on 573 reviews, it’s clear that this experience delivers both comfort and quality.
What makes this tour stand out is its custom approach, allowing you to focus on your preferred wineries or simply enjoy the scenery and sampling. Guides are knowledgeable and friendly, making it easy to learn about Virginia wines in a scenic, pressure-free setting. The price of $499 per group up to three is good value considering the exclusivity and flexibility.
Bottom Line: This private, tailored experience is ideal if you want a relaxed, insider feel with the ability to customize your wine day.
2. Private Charlottesville Area Wine Tour
Number 2 on our list is the Private Charlottesville Area Wine Tour, offering a more intimate experience for about $235 per person. It’s perfect if you prefer a smaller group and more control over your itinerary. The tour lasts around five hours and includes visits to lesser-known vineyards like Merrie Mill Farm and Barboursville Vineyards, which also features historic ruins and seasonal tastings.
What’s compelling here is the flexibility—your guide can craft a route based on your interests, whether it’s exploring boutique wineries or visiting the more established estates. Guests have noted how the guides go above and beyond, with one reviewer praising Jeremiah’s recommendations and friendly chatter. This tour suits those who want a personalized, small-group experience that’s less about the crowds and more about quality.
Bottom Line: Perfect for wine enthusiasts who want a customized, relaxed day with some of Virginia’s best lesser-known wineries.
3. Custom Wine Tour In Black Suburban With Panoramic Sunroof
At number 3, the Custom Wine Tour in Black Suburban elevates the experience with a sleek vehicle featuring a panoramic sunroof. For groups up to six, this five-hour tour offers flexibility to visit favorite wineries like King Family Vineyards or Pollak Vineyards, with options to include dining and sightseeing en route.
What makes this tour unique is its emphasis on style and comfort, plus the ability to fully tailor your itinerary depending on your tastes. The guide can help secure access to top tables and provide insights into the history and landmarks of the region. It’s a good fit for travelers who want to combine luxury with local flavor.
Bottom Line: A stylish, customizable experience for small groups seeking comfort, flexibility, and an upscale feel.
4. Private Wine Tours (Minimum 3 & Maximum 6) Pickup Maximum 30 Miles
Number 4 offers a private wine tour for groups of 3-6, lasting around five hours for $85 per person. It’s designed for those who want to avoid the hassle of driving, with a private guide taking you between Virginia’s top vineyards like Veritas and King Family. The tour includes guided tastings and is flexible to your preferences.
Guests appreciate the ability to customize stops and the convenience of door-to-door service. The reviews highlight friendly guides and well-maintained vehicles. However, some note that the vehicle may be older, so if comfort is a priority, this is something to consider. It’s a cost-effective way to sample multiple wineries with personalized attention.
Bottom Line: A good choice for smaller groups wanting ease, flexibility, and local insights without breaking the bank.
5. Chains, Coffins, & Curses: Charlottesville Ghost Tours
For something completely different, number 5 is the Charlottesville Ghost Tour, rated 4.9/5 with a modest price of $24 per person. In just an hour, you’ll visit haunted sites like the pedestrian mall, Maplewood Cemetery, and hear tales of Thomas Jefferson’s apparitions and colonial slavery.
This tour is perfect for history lovers with a taste for the spooky side. The storyteller guides you through eerie stories and urban legends, making it a fun way to see Charlottesville after dark. It’s short, affordable, and packed with chilling details that make history come alive with a spooky twist.
Bottom Line: Ideal for those interested in the darker stories of Charlottesville and looking for a fun, quick experience.
6. Wine and Culinary Delight Private Tour
Number 6 combines Virginia’s top vineyards with local cuisine on a Wine and Culinary Delight Private Tour. Over about five hours, you’ll visit Barboursville Vineyards, famous for its historic ruins and seasonal pairings, along with Early Mountain Vineyards, known for high-quality wines and spectacular land.
This tour offers a sensory overload of taste and sight, with a focus on pairing wines with gourmet food. Guests rave about the knowledgeable guide and the opportunity to enjoy both wine and architecture. It’s especially suited for those who want a full experience of Virginia’s wine and food scene in one go.
Bottom Line: Best for food and wine lovers who want more than just tastings—an immersive, flavorful journey.
7. 5 Hour Historic Thomas Jefferson Wine Tour
Number 7 is the Historic Thomas Jefferson Wine Tour, focusing on Jefferson’s legacy. It’s a blend of wine tastings at Jefferson’s original sites and visits to Barboursville’s ruins, all within five hours. The guide highlights Jefferson’s influence on the region, with stops at Jefferson Vineyards and the Rotunda.
Guests appreciate the mix of history and wine, especially the visit to Jefferson’s own vineyard. The tour is perfect for history buffs who want to connect Jefferson’s story with Virginia wines. It’s well-paced and offers insights into Jefferson’s architectural and agricultural innovations.
Bottom Line: Great for history and wine lovers eager to connect Jefferson’s legacy with Virginia’s wine culture.
8. The Downtown Mall Food Tour
For foodies, number 8 is the Downtown Mall Food Tour. It’s a three-hour walk through Charlottesville’s vibrant food scene with tastings at five restaurants. Along the way, you’ll see historic architecture and learn about local culture, making this a tasty history lesson.
Guests who love trying different cuisines praise the variety and quality of the food, plus the engaging guide. It’s a great way to experience Charlottesville’s culinary scene if you prefer walking and sampling over wineries or historic sites.
Bottom Line: Excellent for those wanting a fun, food-focused overview of Charlottesville’s lively downtown.
9. Small Group Washington DC to Thomas Jefferson Monticello Day Tour
Number 9 offers a full-day guided tour from Washington DC to visit Monticello and Jefferson’s other sites. It’s perfect if you’re based in DC but want to learn about Jefferson’s world. The 9-hour trip includes guided tours, a visit to Jefferson’s estate, and insights into planting, architecture, and slavery.
Reviews commend the knowledgeable guides and smooth logistics. It’s a comprehensive way to see Jefferson’s estate while also visiting the historic University of Virginia. It’s well-suited for history buffs who want a fully narrated experience.
Bottom Line: Ideal for DC visitors eager to combine history, architecture, and scenery in one day.
10. Private Arrival Transfer from Charlottesville Airport (CHO)
Number 10 is a straightforward private airport transfer costing about $49.60 per person. It’s perfect if you want a hassle-free start to your trip, with door-to-door service from Charlottesville International Airport. The driver, like Terri, is described as friendly and professional, ensuring a smooth transition from plane to hotel or other destination.
This service is reliable and convenient, especially if you’re arriving late or with lots of luggage. It’s a practical choice for travelers who want to skip the taxi lines and enjoy a personal, comfortable ride.
Bottom Line: Smart for arriving or departing without fuss, especially if you’re flying into Charlottesville.
$49.60 per person
11. Private UNESCO World Heritage Tour
For those interested in architecture and culture, the Private UNESCO World Heritage Tour visits Jefferson’s University of Virginia and Monticello, both recognized for their cultural significance. The six- to seven-hour trip includes guided tours of iconic buildings, the gardens, and the historic farm. It’s designed for visitors wanting a deep dive into Jefferson’s visionary projects.
Guests note the detailed guides and the chance to see two of America’s most important historic sites in one day. It’s perfect for travelers eager for an in-depth, educational experience.
Bottom Line: An excellent choice for history and architecture enthusiasts wanting a comprehensive cultural tour.
$305.00 per person
12. Charlottesville Challenge Scavenger Hunt
Number 12 is the Charlottesville Challenge Scavenger Hunt, rated 4.0/5. This interactive experience invites you to explore the city with a live remote host, answering trivia and solving clues. It’s a fun, active way to learn about Charlottesville’s hidden spots and cultural history.
Perfect for groups up to 10 who enjoy problem-solving and friendly competition. The app-led format makes it flexible and engaging, especially if you want a break from traditional tours.
Bottom Line: Fun and interactive, great for families or groups seeking a unique way to explore.
13. Charlottesville: Best Vineyards Private Tour (Up to 14 people)
Number 13 is a private group tour for up to 14 people, lasting about six hours. It visits Early Mountain Vineyards, with its historic land and Bordeaux-style wines, and King Family Vineyards, known for its scenic setting and premium offerings.
Guests appreciate the flexibility of the itinerary and the chance to visit several top wineries in one day. The tour balances scenic views, quality wines, and a social atmosphere—ideal for larger groups celebrating together.
Bottom Line: Best for groups wanting a comprehensive, social wine experience with scenic vistas.
$969.00 per group (up to 14)
14. University Scavenger Hunt: Grounds Explorers
This UVA scavenger hunt offers a fun, interactive way to explore the University of Virginia campus. It’s perfect for students, families, or anyone wanting a quick, engaging activity. The hunt uses an app to guide you through landmarks, trivia, and challenges in about 1.5 hours.
It’s a light-hearted way to learn about UVA’s architecture and notable figures. Reviewers found it enjoyable but note the limited depth—more of an entertaining overview than a rigorous historical tour.
Bottom Line: Good for a quick, fun visit to UVA with friends or family.
$14.99 per person
15. Charlottesville Dark History Ghost Tour
Rated 3.0/5, this Dark History Ghost Tour explores Charlottesville’s haunted sites at night. Over an hour, you’ll learn stories of the Moon Ghost, James Madison’s spectral encounters, and haunted cemeteries.
It’s suited for those interested in spooky stories and local legends, offering a spooky twist on the city’s past. The stories are atmospheric, but some reviews suggest the experience is not as intense as other ghost tours.
Bottom Line: Good for fans of ghost stories and historic tales with a darker edge.
$24.00 per person
16. Self-Guided Scavenger Hunt: Centuries of Charlottesville
Finally, the Self-Guided Scavenger Hunt offers a flexible way to explore Charlottesville at your own pace. Filled with trivia, challenges, and clues, it takes about two hours and is perfect for small groups wanting independence.
It’s a budget-friendly, fun option for those who like to explore on their own while still having some structure. The reviews note it’s a good way to see key sights with a playful twist.
Bottom Line: Best for independent travelers who want an interactive, affordable way to see Charlottesville’s sights.
$14.99 per person
How to Choose Your Perfect Charlottesville Tour
When selecting a tour, consider your budget, time available, and what excites you most—wine, history, food, or spooky stories. For wine lovers, the private Virginia Private Custom Wine Tour offers a luxurious, customizable experience, while the Wine and Culinary Delight combines tastings with gourmet food. If history is your passion, the UNESCO World Heritage Tour provides an in-depth look at Jefferson’s masterpieces.
For those seeking fun and interactive exploration, the Charlottesville Challenge and self-guided hunts are excellent choices, especially for families or groups. Ghost stories? The Charlottesville Ghost Tour offers spooky tales in a quick, affordable format.
Lastly, consider the group size, activity level, and best time of year—spring and fall are especially beautiful for vineyard visits and outdoor tours. Booking early, especially for popular experiences, ensures you get your preferred date and time.
Final Thoughts
Charlottesville’s diverse range of tours means there’s something for every traveler—from wine aficionados and history buffs to foodies and thrill-seekers. If you’re after a luxury wine experience, the private custom wine tour will deliver. For a more active, fun outing, try the Challenge Scavenger Hunt, or if you’re curious about Charlottesville’s haunted past, the Ghost Tour is a spooky treat.
Whatever your interests, planning ahead — especially in peak seasons — will help you make the most of your trip. Charlottesville’s historic charm and scenic beauty are waiting, so don’t hesitate to book early and secure your spot for an unforgettable experience.