Top Charlottesville Tours, Sightseeing & Cruises

Discover Virginia’s Monticello Wine Trail on a private winery tour in Charlottesville. Create an itinerary with your dedicated guide based on your group’s wine interests and travel in a comfortable vehicle to each destination. Enjoy guided tours of each vineyard, play indoor games, and purchase wine tastings, if you’d like.

This private self-guided tour offers independent travelers the freedom to set their own pace and start time while driving through Shenandoah National Park. After downloading an app, listen to audio that reveals secrets about Shenandoah’s history and its most impressive landmarks. Enjoy the flexibility to stop for photos or hikes in your own car without group constraints.

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 and unforgettable experience for you and your guests to truly savor every moment. On this thoughtfully curated tour, you’ll be enjoying visits to 3 carefully selected wineries located on the scenic eastside of Charlottesville. This journey will take us through the charming Keswick area, once home to Thomas Jefferson’s old stomping grounds, a region rich with history, natural beauty, and timeless elegance.

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 stops is also recognized for its architectural design, while the other for its architectural ruins.

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 significance. Our journey begins with a detailed guided tour of the picturesque University Lawn and the distinguished Rotunda at the University of Virginia, where history and architecture blend beautifully. Next, we head to Monticello's David M. Rubenstein Visitor Center, a thoughtfully designed space featuring an excellent gift shop and numerous engaging exhibitions dedicated to Thomas Jefferson and the rich history of Monticello. For a convenient and pleasant break, you can enjoy a quick bite and refreshing drink at the Monticello Farm Table Cafe before proceeding to your in-depth guided tour of the historic estate.

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 natural wonders of the Blue Ridge Mountains. Encounter sweeping overlooks, hidden waterfalls, and captivating tales of the land's past as you cruise along. Perfect for both newcomers and seasoned travelers, this tour lets you explore at your own pace—just drive, look, and listen to the stories unfold along the way. — Self-guided audio experience through Shenandoah National Park — Explore over 100 miles of scenic mountain roads at your own pace — Learn about the geology, history, and local lore of the Blue Ridge — Ideal for first-time visitors and seasoned explorers alike

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 celebrated wines, you will be completely immersed in the rich history shaped by Thomas Jefferson’s lasting influence on the region. This experience promises to be both relaxing and enlightening, blending the natural beauty, exquisite flavors, and historical depth unique to this area.

Explore Virginia wine country in comfort and style with your own private chauffeur. This experience is perfect for couples or small groups looking to enjoy the best wineries and breweries around Charlottesville without worrying about driving or planning. You'll ride in a luxury SUV and visit 2-4 top wineries or breweries such as: King Family Vineyards Pippin Hill Farm & Vineyard Veritas Vineyard & Winery Highlights: -Private SUV (up to 6 guests) -Door-to-door pickup -Custom itinerary -Local knowledgeable driver Duration: 4-6 hours Why Guests Love It: Stress-free experience Flexible schedule Perfect for special occasions Saturday availability is limited and books quickly.

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 Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

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Download GuideAlong’s self-guided audio tour bundle to make the most of your Eastern USA road trips. As you drive, hear stories play automatically as you explore scenic drives, national parks, lakeshores, and historic parks. This is the ultimate collection of 14 iconic destinations, including Acadia, Blue Ridge Parkway, Catskills, Florida Keys, Great Smoky Mountains, Lake Superior, Outer Banks, Shenandoah, and Vermont’s Route 100. A memorable adventure awaits on America's iconic roads. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. Stories, tips, and directions play automatically based on your location Travel at your own pace Tour offline using GPS. No cell service or WiFi is needed Suggested itineraries for half, full, or multi-day use Buy once, use forever! No expiry, includes free updates Like having a tour guide along for the drive Purchase one bundle per vehicle.

With the beauty of the Blue Ridge Mountains surrounding the quaint vineyards of Virginia, this private wine excursion delivers a peaceful and harmonious experience in the great outdoors. A private chauffeur will cruise you and your guests from historic Charlottesville to the countryside. Spend the day touring the area and sampling wines from multiple wineries. On the Wine Trail, you’ll have your choice of which tasting rooms to visit and when to have a picnic lunch.

The Dairy Market is among Charlottesville's leading food, retail, and entertainment venues. Free parking is available onsite.

The Downtown Mall Food Tour is a unique and memorable way to visit one of America's top college towns.

The best way to spend your World Cup 2026 off-days in New York City & surrounding areas Visit three major eastern US national parks in one trip! Explore the Great Smoky Mountains, hike to a 360-degree observation deck, and visit the New River Canyon Bridge. Walk along Shenandoah National Park's Skyline Highway and discover Loli Cave's ancient stalactites. Enjoy a rodeo, southern food, and the Titanic Museum in Pigeon Forge. Fun & Insightful Bilingual Tour Guides – Enjoy lively stories and spontaneous sharing along the way. Unlimited Bottled Water & Complimentary Snacks – Stay refreshed and energized throughout the journey. Themed Attractions with Seasonal & Adventurous Highlights – Carefully selected for excitement and discovery. Happy Family Time – Kids enjoy 50% off for a budget-friendly trip in July & August. Exclusive Travel Keepsakes – Includes a custom travel passport and share-worthy moments for social media.

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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 sheep and cattle, with your sommelier-guide.