Top Virginia Private Sightseeing Tours

America turns 250 only once. Williamsburg has been waiting for this moment longer than any other city in the country. This is where colonial America was debated, governed, and defined — where the ideas that became the United States were argued on the street corners, in the taverns, and in the Capitol building at the end of Duke of Gloucester Street. On this private 2-hour walking tour, your dedicated guide brings the 18th century to life with insider stories, behind-the-scenes history, and personal commentary you will not find in any guidebook. The Williamsburg Inn, Merchants Square, Bruton Parish Church, the Governor's Palace, and the Capitol — each stop on this tour is a chapter in America's founding story. In 2026, walking these streets carries a weight no other destination can match. This is not a museum. This is a living city. And in America's 250th year, it has never felt more alive.

Orange, Virginia produced two U.S. presidents and once served as Robert E. Lee's Confederate headquarters — remarkable for a small Piedmont courthouse town. This self-guided walking tour traces how that power was built, exercised, and withheld, down to a train depot blueprint that once labeled its waiting rooms by race. Confederate cavalry once charged down Main Street with sabers drawn — rare urban combat for the Civil War. The county courthouse served as Lee's nerve center that winter, when 60,000 troops camped in the surrounding fields. A Caroline Street church built with Jefferson's own craftsmen went from Confederate prayer hall to Union stable. The African American Commemorative Park closes the loop, honoring the Mill Street community that lived one block away — present, but long overlooked. Perfect for history lovers who read the fine print as closely as the plaques. Install the VoiceMap app and enter the code from your confirmation email to download and start touring.

Get a taste of Alexandria's Mediterranean coast and diverse history without having to sort out transportation with this private tour. Visit the Citadel of Qaitbay, built where Alexandria's ancient lighthouse stood, then explore the Bibliotheca Alexandrina, a reimagining of the city's ancient library. Finish with a drive along the Corniche. Admission fees are not included.

Gordonsville, Virginia has been a crossroads of American life for more than two centuries. On this self-guided walking tour, you'll trace how every shift in transportation – from stagecoach to steam engine to automobile – left its mark on this small town. You'll also discover how the women excluded from its formal economy turned that exclusion into one of the most remarkable entrepreneurial stories in American history. The tour starts at the Gordonsville Visitor Center on Main Street, where you'll walk north past sixty years of railroad-era architecture – merchant homes with elaborate porches, four historic churches built within thirty years of each other, and a street whose survival owes everything to the town's gradual decline. Along the way, you'll visit the site of Gordon's Tavern, where a historical marker lists Washington, Jefferson, Madison, Monroe, and Lafayette among those who stopped here.

Private Shadows of the Past: Tracing Slavery’s Legacy Tour invites you to embark on a deeply moving journey through history, remembrance, and resilience. Walk through places that preserve the echoes of lives shaped by slavery and discover the powerful stories of those who endured injustice while holding on to hope, dignity, and the dream of freedom. Through meaningful historical insights and reflections on the generations who fought for equality, explore how this painful chapter shaped communities and continues to influence society today. Each stop offers an opportunity to honor the voices of the past, recognize the strength of the human spirit, and reflect on the enduring importance of justice and humanity. This thoughtful experience goes beyond sightseeing, inviting you to listen, learn, remember, and carry these stories forward. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

This is my favorite tour - I pick up from your Williamsburg hotel to visit Berkeley, Westover and Sherwood Forest Plantations. Berkeley’s 1726 Georgian mansion is the birthplace of Benjamin Harrison V, signer of the Declaration of Independence, and also the birthplace of William Henry Harrison, 9th U.S. President, and his grandson, Benjamin Harrison, 23rd U.S. President. During the Civil War, Berkeley was occupied by General McClellan’s troops. While at Berkeley, General Butterfield composed the familiar tune “Taps”, played by his bugler. We will explore the Native American, Colonial and Civil War artifacts, along with historical paintings and exhibits in the 18th century basement museum. At Westover, we tour the grounds of this beautiful Georgian mansion, its amazing gardens and secondary buildings. At Sherwood Forest, we tour the grounds of our 10th U.S. President, John Tyler's home, the longest frame house in America. If scheduling in advance, we can request an interior tour.

Embark on a private excursion from Alexandria to Rosetta, a city steeped in Islamic heritage. Delve into the Rosetta Museum, meander through 18th-century streets lined with historic homes, and explore the Citadel of Qaitbay, the site where the famed Rosetta Stone was found. Witness the meeting of the Nile River and the sea, before heading back to Alexandria.

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.

Explore the best that the United States capital has to offer when you book this half-day, private sightseeing tour by mini-bus. Tours can accommodate up to 30 people, great for company events or large parties, and itineraries are completely customizable. Choose to see top monuments like the White House, Lincoln Memorial, and National Mall, or make stops at any location of your choosing in the district.

Looking for Washington DC private tours? Explore DC with World’s Five Star Limo Service. This Mercedes Van Tour is for up to 14 people. We provide pick up and drop off at any desired place in Washington DC, Virginia and Maryland. Distinguish customer service, modified limos and reliability shape our Tour Quality. Capture yourself in front of most of the historical buildings in the shortest possible time.

Delve into the nation’s military history with a twenty-year Navy veteran as your guide on a private tour. Choose from an extensive list of museums, monuments, memorials, battlefields, cemeteries, and even the Pentagon (90 day advanced notice required) on an exclusive tour of Washington, DC and surrounding areas. Get unmatched insights and history and spend the day walking through the pages of a real life history book.

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.

Get acquainted with the history of the United States Marine Corps on this guided, 6-hour, small group tour in Washington DC. From the Marine Corps War Memorial, aka the Iwo Jima Memorial, to the Marine Barracks, Marine Corps Base Quantico, and the National Museum of the Marine Corps, expert guides provide unique and detailed information. This intimate tour provides an incredible historical experience for those with an interest in the US Marine Corps. Lunch, entry fees and a local hotel pickup and drop-off are included.

Are you looking for a way to see Old Town Alexandria without joining a tour group? Explore at your own pace with this affordable walking tour. • Find out how a banker’s wife hid a portion of the George Washington family fortune in her underwear drawer during a Union raid • Hear from producer Rick Snider, an award-winning Washington journalist and tour guide • Do it all in an hour or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

Explore some of the most famous landmark locations around Old Town Alexandria, Virginia on this 90-minute Civil War-era walking tour. See the many historic 17th- and 18th-century homes, hear colorful stories about its founding father and discover little known facts about all the monuments, statues and buildings in the area. Visit the historic mansion and gardens of the Carlyle House; Christ Church, where George Washington worshipped; the Stabler-Leadbeater Apothecary Shop, now preserved as a museum and more. Any necessary entrance fees are included.

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

America turns 250 in 2026. The celebrations are deserved. But the full story of those 250 years includes voices that were long left out of the official account. This private 2-hour walking tour traces the history of slavery in Colonial Williamsburg — the legal systems that enforced it, the buildings where enslaved people lived and worked, the courts that judged them, and the legislature that debated their lives as political abstractions. Your dedicated guide does not simplify this history or soften it. They bring it to life with care, context, and humanity. Colonial Williamsburg, the Courthouse, the Capitol Building, and the James Geddy House — each stop reveals a different dimension of a society built on enslaved labor. Understanding this history is not separate from celebrating America's 250th anniversary. It is essential to it.

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.

Time travel to 1775 with a private tour and explore the birth place of American history. Points of interest include: 1) Walk the Duke of Gloucester Street while learning about colonial trades, power of the press and Virginia's leadership in shaping our early Nation, including the first Continental Congress, Declaration of Independence & Declaration of Rights 2) Admire the Capitol Building and understand why America's Constitution carved out three government branches 3) Enjoy the Palace Green and the Governor's Palace where townspeople and gentry celebrated important events 4) Learn about Bruton Parish Church, closes 4PM 5) Shop in Merchant's Square 6) Visit the Sir Christopher Wren building and learn why the oldest academic building in America plays a significant role in our history Note: Colonial Williamsburg (CW) hours are 10am-5pm.

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.

Uncover the full beauty of Jersey on this 7-hour private shore tour blending dramatic coastlines, serene countryside, and centuries of island history. From medieval castles and seaside villages to sweeping bays and wartime relics, experience the island’s most iconic landmarks with your knowledgeable driver-guide. Perfect for those who wish to see it all — from west to east — in one unforgettable day.

Private Customizable Walking History Tour in Williamsburg invites you to step back in time and uncover the fascinating stories behind one of America’s most historic destinations. Wander along charming streets lined with colonial architecture, discover remarkable landmarks, and explore the heritage that shaped early American life. With a private guide and a customizable route, you can focus on the historical sites, hidden corners, and captivating stories that interest you most. From the echoes of colonial times to the people and events that influenced the nation’s history, every stop offers a fresh perspective on Williamsburg’s enduring legacy. Enjoy a relaxed and personalized journey filled with cultural discoveries, intriguing details, and memorable photo opportunities at your own pace. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

giving you the history, hidden details, and insider perspectives you won’t get on a standard tour. Every stop is interactive, personalized, and designed to make you feel like you’re experiencing the city, not just looking at it.