Top Virginia Holidays

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. Tours are private, no sitting with strangers, perfect for families, couples and visitors with pets. Short on time? 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!

Watch the sun set over Chesapeake Bay on a 2-hour, small-group dolphin tour by kayak from Virginia Beach. Paddle along the coast as you spot Atlantic bottlenose dolphins, and see the Cape Henry Lighthouses and Chesapeake Bay Bridge Tunnel from the water.

Enjoy a night of drinking and ghost stories as you explore Williamsburg with the help of a tour guide to show you around. Stop at a range of local establishments for drinks and pass by historical sights on the way while you listen to the macabre tales told by your engaging tour leader. Make sure you come thirsty for some drinks and hungry for some thoroughly researched spooky stories.

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.

Build your wine confidence. No snobs here! White & Red Wine Crafting, Aeration Techniques, Rosé Revelations, Restaurant Etiquette, Molecular Pairing, Chocolate and Wine Pairing made easy!

Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!

You've been to winery wine tasting, but, have you been to a chocolate factory wine tasting? Welcome to our craft chocolate factory to see how chocolate is made while sipping on perfectly paired wine.

Come on to our Haunted Pub Crawl Tour presented by US Ghost Adventures! Many of the best clubs and pubs in the area are housed in the historic structures that dot the Shockoe Bottom neighborhood of Richmond. This trip is created to give you a taste of the best Richmond has to offer, like Farmhouse hard cider, as well as a window into the afterlife of some of its people, such as the four ghosts rumored to haunt St. John's Church.

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.

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, air-conditioned vehicle to each destination. Enjoy guided tours of each vineyard, play indoor games, and savor included snacks during the tour. Purchase wine tastings, if you’d like.

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.

Take this Alexandria Boos and Booze haunted pub crawl tour and add some fun into your work week! This quick but fun tour will take you to four stops for up to two hours. This tour price does not include tastings or tours of the facilities. This tour will take you to a total of four watering holes in Alexandria, which may be a combination of craft producers in Alexandria, and local bars. There will be a variety of haunted stops in between these already notorious bars and pubs! We'll spend about 15-20 minutes to one hour at each destination. Exact lineup depends on day of week and season. Drinks are not included. The total duration is approximately 1 hour and 45 minutes. The duration of the tour includes, drinks at the establishments, history and story telling at the historic sites and walking to and from the historic sites.

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.

Join us for haunting tales of Richmond's Court End neighborhood on a guided walking tour. Take in a unique urban landscape where historic and modern Richmond come together in dramatic fashion, with historic homes, medical buildings, museums, and more. See the home of America's most renowned Supreme Court Chief Justice and hear about the tragic tales that have resulted in hauntings within the historic house. Learn about a grim resurrectionist who terrified the community in the 1800s and continues to frighten medical students in an architecturally stunning Egyptian building. Move through the neighborhood and learn how the regal historic structures and gleaming veneers of modern Richmond belie the tumultuous and eerie history that remains just below the surface.

Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration! Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza. Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll! With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!

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.

This exclusive, private tour (only your group) highlights Colonial Williamsburg's Christmas traditions and picturesque holiday decorations of our historical area. This tour provides insight about the materials, crafts people, construction and design of the wreaths and garlands adorning the exterior of most 18th Century buildings, exhibits and private homes and different judging categories. We meet at The Williamsburg Inn to admire the decorations and begin our journey to the Duke of Gloucester. We'll discuss how holidays were celebrated in 17th and 18th Centuries here in Virginia including plantations, our Capital cities and during the Revolutionary War (e.g., Continental Army). Holiday biscuits by African descendants or traditional gingerbread cookies are offered. If before 7PM, we offer hot beverages. Note: Grand Illuminations are the 1st, 2nd and 3rd Saturdays of December (7pm fireworks). The Yule Log lightings are the first, second and third Fridays of December.

The Ghost Tour is Williamsburg's first and only murder-focused tour. Explore areas that other history tours would be afraid to visit. Explore a historic city that conceals a sinister and unsettling past. A netherworld of horrific death and hatred. Accompany your guide on foot to some of our favorite local watering establishments. To help you get ready for what's to come, try a drink with a murder theme or one of the pub's specialty beverages. Then, take a stroll through the dim, peaceful streets of Historic Williamsburg, where you may learn the real stories of the city's most notorious crimes. There's nothing ghostly about Williamsburg's scariest tour. It has to do with murder.

Discover Virginia Wine Country the way it was meant to be experienced—privately, comfortably, and entirely on your schedule. Skip the crowded buses and cookie-cutter itineraries. This fully private experience is designed exclusively for your group, allowing you to explore Charlottesville's renowned wineries, breweries, cideries, and distilleries at your own pace while traveling in a luxury Chevrolet Suburban featuring a panoramic sunroof. Whether you're celebrating a special occasion, planning a romantic getaway, reconnecting with friends, or simply looking to experience the best of Virginia wine country, our local concierge team helps create a seamless day from start to finish. 100% Private Tour — No strangers, no shared transportation, no fixed schedule. Customized Itinerary — Visit the wineries, breweries, cideries, & tasting rooms that match your group's preferences. Local Expertise — Our team knows the region's hidden gems, iconic vineyards, and reservation-only experiences.

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.

Have you ever wondered how our modern Christmas traditions began? Join us for a 1-hour walking tour through the streets of Colonial Williamsburg, where your guide will reveal the colonial Christmas celebrations that shaped our current traditions. You'll also learn how the decorating style of Colonial Williamsburg influenced decorations across the nation. Shades of Our Past is not affiliated with Colonial Williamsburg; therefore, this tour does not include entry to any buildings owned by Colonial Williamsburg. The tour takes place through the streets of Colonial Williamsburg and is subject to weather conditions. Please be prepared for various weather scenarios. Additionally, the advertised tour route may change based on activities in the Historic Area. Please note that tours may be unavailable on certain days due to staff participating in other events. For more details about these programs, please visit our website.

Take the stress out of your family excursion in Charlottesville with this private round-trip transfer from Pantops Shopping Center to the destination of your choice. Skip the guesswork of ride-sharing services or taxis and schedule your pickup in advance, then head straight to your excursion location—including wineries, sights, parks, concerts, or other destinations. Enjoy a few hours of free time to enjoy your family activity before the return trip to the pick-up location or other drop-off point.

Immerse yourself in the excitement of Richmond, Virginia’s thriving craft beer scene—and learn all about beer styles and the brewing process from your guide—on this private, half-day tour. Meet your guide in central Richmond for a tutored tasting before setting off in your comfortable, air-conditioned minibus. You’ll visit three highlight breweries, will enjoy generous tastings at each, and will go behind-the-scenes at one to learn more about the brewing process.