Top Charlottesville Private Sightseeing Tours

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.

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.

Turn a day in Virginia wine country into a seamless experience. Our private wine & beer tours are designed for couples, small groups and anyone looking to enjoy the best of the Monticello Wine Trail without worrying about driving, planning or logistics. Whether you're celebrating a birthday, planning a girls day, or just want a relaxing afternoon, we make it effortless from start to finish. Your experience includes: 6 hours Private, luxury vehicle Custom itinerary or let us plan it for you Door-to-door pickup and drop-off Flexible timing & personalized experience

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 history, unique geology, and vibrant wildlife, including black bears and deer. Ideal for travelers looking to explore at their own pace, this tour highlights hidden gems and provides insights into the area's Native American heritage and the impact of the Civilian Conservation Corps. - Drive the iconic 105-mile Skyline Drive with breathtaking views - Visit historical sites like Dickey Ridge Visitor Center and Rapidan Camp - Enjoy popular hiking trails, including Stony Man and Dark Hollow Falls - Suitable for all types of visitors, from short-day explorers to multi-day adventurers

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

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.

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.

Your tours are intentionally designed for small groups, allowing us to provide a level of service and attention that larger tour operators simply cannot match. We take the time to understand your preferences, recommend venues that fit your group's personality, and create an itinerary tailored to your occasion. Whether you're celebrating a birthday, anniversary, bachelorette party, date day, or simply enjoying time with friends, every experience is customized around you. What truly makes us different is your concierge-style approach. From the moment we pick you up until we safely return you home, we're focused on the details. We coordinate timing between venues, help keep your day running smoothly, offer local knowledge of Virginia wine country, and provide the flexibility to adjust the day as needed.

What makes this experience unique is that every hike is completely private and personalized to your interests, abilities, and pace, allowing you to enjoy a day outdoors designed specifically for your group. There are no crowds, no rigid itineraries, and no one-size-fits-all routes. Following a pre-trip consultation, your guide custom-maps a hike that aligns with your fitness level and adventure goals, ensuring a more meaningful and enjoyable experience. We handles every detail, including private door-to-trailhead transportation, hiking logistics, gear coordination, and field-prepared meals, so you can focus entirely on the surrounding landscape. Each trip is led by a Wilderness First Responder-certified professional and supported by satellite communication technology for enhanced safety and connectivity, delivering a seamless, personalized, and professionally guided wilderness adventure.

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.

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.