Top Virginia Private Sightseeing Tours

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.

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 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.

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.

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

Join us on a captivating 2-hour small group boat tour of Chincoteague and Assateague Island, guided by the knowledgeable local guides as we explore the beautiful coastline in search of the famous Wild Assateague Ponies. Our tours allow us to navigate and explore areas that other tours cannot. Along the way, we search for osprey, eagles, dolphins while you local guides provide an informative but laid back overview of the island and its rich history. Book your private tour today and prepare for an exhilarating journey into the heart of the island's natural beauty.

During this one-hour walking tour, discover how a sleepy southern town was restored to its former colonial splendor through the dream of Dr. W.A.R. Goodwin and the backing of Mr. John D. Rockefeller, Jr. We will discuss the restoration of Colonial Williamsburg from its conception through to the continuing restoration efforts. We encourage questions and conversation so all guests can better understand why Williamsburg was, and is, so important not only to Dr. Goodwin and Mr. Rockefeller but also to future generations. Please note: Due to staff participation in other events, tours may be unavailable on some days. Please see our website for information. *Shades of Our Past is not affiliated with Colonial Williamsburg; therefore, this tour does not include entrance or admission into Colonial Williamsburg-owned buildings. Since the tour is through the streets of Colonial Williamsburg, it is weather contingent. Please be prepared for all weather conditions.

During this 1-hour walking tour, learn the complexities of Virginia's decision to seek independence from England. Discover the challenges faced by the men of the House of Burgesses as they ultimately chose to declare Virginia's independence and learn how this pivotal decision influenced the Continental Congress in Philadelphia. Please note: Due to staff participation in other events, tours may be unavailable on some days. Please see our website for information. *Shades of Our Past is not affiliated with Colonial Williamsburg; therefore, this tour does not include entrance or admission into Colonial Williamsburg-owned buildings. Since the tour is through the streets of Colonial Williamsburg, it is weather contingent. Please be prepared for all weather conditions.

*FOR MATURE AUDIENCES ONLY-AGES 17 +* During this one-hour walking tour, hear the darker side of 18th-Century Williamsburg. Stories of murder, mayhem, and scandal--those things talked about in taverns, back alleys, and the courts--straight from the town's citizens. Each tour will be different, and the stories are a-plenty. Due to the sensitive nature of the subjects and the salty language of the time, this tour is recommended for mature audiences 17 and older. Please note that since every tour is different, the routes advertised may also differ. Please note: Due to staff participation in other events, tours may be unavailable on some days. Please see our website for information. Shades of Our Past is not affiliated with Colonial Williamsburg; therefore, this tour does not include entrance or admission into Colonial Williamsburg-owned buildings. Since the tour is through the streets of Colonial Williamsburg it is weather contingent. Please be prepared for all weather conditions.

Be transported back to Williamsburg in 1943 in this 1-hour character tour. Learn how the citizens of the town are dealing with rationing, blackout drills, and all the new servicemen in town during the Holiday season. Please note that each tour is unique, so the advertised routes may vary. You will be guided through town by either a USO Hostess or an Air Raid Warden. However, for evening tours, the guide will solely be an Air Raid Warden. Routes may also be changed to accommodate activities in Colonial Williamsburg. Shades of Our Past is not affiliated with Colonial Williamsburg; therefore, this tour does not include entrance or admission into Colonial Williamsburg-owned buildings. Since the tour is through the streets of Colonial Williamsburg it is weather contingent. Please be prepared for all weather conditions. Please be aware that due to staff participation in other events, tours may be unavailable on certain days. For details about these programs, please visit our website.

Download GuideAlong's Yorktown Battlefield audio tour to see the landmarks of the 1781 Siege of Yorktown. This 10-mile driving tour of the Yorktown Battlefield points out each landmark of this final major conflict. See fortified Redoubts 9 &10, where the British tried to stave off the American advance. At the Yorktown Victory Monument, a 210-foot-tall obelisk honors the fallen. Visit the original site of Washington’s Headquarters, the French Artillery Park, and the Grand French Battery, and Surrender Field before ending the driving loop near the Yorktown Visitor Center. 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 No time limits or expiry, and free updates

We do sanitized all our vehicles after each tour. To provide a smooth and stylish travel experience, we only utilize top-notch, freshly cleaned and sanitized vehicles, like luxurious limos and comfortable minibuses. Our large fleet is made to accommodate a wide range of tastes and needs, ensuring that every part of your journey is managed with the highest level of comfort and elegance. Since 1998, we have merged our in-depth knowledge of the business with a profound comprehension of the demands of our customers to guarantee that each tour is specially designed to continuously surpass expectations. We prioritize your safety with regular hygiene practices, regular vehicle maintenance.

Perfect for Individuals or Small Groups. We offer guided tours, concierge service and airport transfers throughout the Washington DC , Maryland and Northern Virginia areas.

This is a special tour, that no one in virginia is giving the opportunity to experience except here. This a hidden gem in Virginia that will give you a very fun, exciting, and memorable experience that you will love. It’s special because you get to immerse in many elements of nature by us hiking, swimming in fresh waterfalls, then relaxing with wim hoff breathwork surrounding a campfire with a magnificent scenery that makes you feel away from the world in peace. With a recommendation of a hotspot for food that's a nourishing delicious meal at the end.

Let's go back in time together! Colonial Williamsburg’s historic area covers 10 blocks, making a private walking tour with a licensed local guide a fun, practical way to see its main sights. Walk from the Williamsburg Inn along Duke of Gloucester St, viewing the Capitol, trades and shops, horse-drawn carriages, and the Governor’s Palace while learning about Virginia’s colonial history and the move toward independence. Discover the spots only a local knows, like formal gardens, hidden sheep, and a bakery with 18th-century cookies. The route concludes at Bruton Parish Church near Merchants Square, where you can continue exploring, shop, or grab a bite. The tour can be customized to your interests and covers up to 1.5 miles. Guests are saying: “We rank Cyndi in the top 2% of professional guides we’ve experienced.” “She knows her history and shows a lot of enthusiasm for it.” “She was a pleasure to be with.”

Embark on an unforgettable Northern Virginia winery tour, led by a certified Sommelier who has extensive knowledge about wines from around the world, and specifically Virginia Wine. The tour will take your group to three exceptional wineries in the region. Relax in a comfortable private vehicle as you explore the picturesque landscapes of the serene Virginia countryside. Enjoy expertly guided tastings, behind-the-scenes experiences, and personalized service tailored to your preferences. Whether you're celebrating a special occasion or simply indulging in a luxurious day of wine exploration, our curated tours offer an unparalleled experience. Discover the finest wines Northern Virginia has to offer with a unique, VIP experience!

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.

Led by a retired FBI historian and surveillance expert, this small-group tour uncovers hidden Black heritage sites across Northern Virginia, blending powerful storytelling with real history. Guests explore authentic landmarks such as Freedom Hill, Tinner Hill, and a historic courthouse while hearing untold stories of resilience, community, and freedom. This tour is more than sightseeing, it’s a moving journey through America’s Black past that travelers won’t forget.

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

Explore the rich history of Staunton with a guided tour in the guide's vehicle that takes you through all six Historic Districts. Discover the town's unique architecture, beautiful vistas, and historic cemeteries, all while listening to intriguing stories from a professional tour guide. A highlight includes a visit to Trinity Episcopal Church, showcasing stunning stained glass windows by Tiffany and Sons (subject to availability). Perfect for history buffs and architecture enthusiasts alike, this tour offers a comprehensive experience of Staunton's rich heritage. - Visit all six Historic Districts of Staunton with a knowledgeable guide Augusta County Courthouse, Beverley Mansion, Rail station, American Hotel, Stuart Mansion, several historic churches, more - Discover unique architecture and beautiful vistas throughout the town - Enjoy guided tour of Trinity Episcopal Church and its Tiffany stained glass - Ideal for history lovers and those interested in local culture and architecture

Step back in time on a private ride through historic Fredericksburg in a fully restored 1920's Model-A. Guests meet in the heart of downtown and climb aboard cushioned seats for a 20-30min tour with open-air views and plenty of charm. Along the way you'll pass Fredericksburg's most treasured landmarks including the Mary Washington House & Monument, Huge Mercer Apothecary, Kenmore Plantation, Chatham Manor, and the Rappahannock Riverfront. Your guide shares fascinating stories of colonial times, the Civil War, and Fredericksburg's unique past while you relax and enjoy the ride. This tour is the ideal way to enjoy Fredericksburg highlights with history, nostalgia and fun all rolled into one unforgettable experience. Remember Don't Just Look at History, Ride in It!

Uncover the dark side of Norfolk’s recent and distant past alike on this guided exploration of Norfolk’s true crime stories. From newsmen murdered in the street, to corrupt misdeeds of the powerful, respected mayors turned murderous, and the dark past of some of the city’s most iconic landmarks,

Experience the natural beauty of Shenandoah National Park as you set out on a scenic 4-mile moderate hike along the Rose River Trail, where you’ll be immersed in lush forest landscapes and the soothing sounds of flowing water. As you follow the winding trail, you’ll encounter a series of picturesque waterfalls cascading over moss-covered rocks, offering perfect opportunities to pause, relax, and capture stunning photos. Along the way, you’ll enjoy the peaceful atmosphere of the Blue Ridge Mountains, breathe in fresh mountain air, and take in the rich sights and sounds of the surrounding wilderness. This well-balanced hike gives you the chance to combine light adventure with moments of tranquility, making it an ideal outdoor experience for nature lovers looking to explore one of Virginia’s most iconic national parks.

Colonial Williamsburg’s historic streets and preserved buildings are the backdrop for a private walking tour led by a local guide. Over roughly two hours, the route includes Bruton Parish Church, the Capitol Building, the Governor’s Palace, and Duke of Gloucester Street, with stories about 18th-century daily life, religion, colonial government, and Williamsburg’s role in the nation’s beginnings.