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. 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.

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.

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.

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!

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.

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!

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.

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.

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.

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!

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.

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 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.

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.

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.

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 tour explores the historic and cultural heritage of Williamsburg during the Christmas season through a refined and immersive journey. Walk through a preserved Old Town where colonial architecture and festive traditions reflect a history older than the United States. Begin near the Visitor Center, where seasonal décor highlights the city’s enduring cultural heritage. Continue to the St. George Tucker House, an elegant example of colonial architecture enriched by traditional holiday presentation. Visit Bruton Parish Church, a landmark shaped by centuries of spiritual and cultural legacy. Stroll along Duke of Gloucester Street, where historic surroundings reveal the atmosphere of early American life during the festive season. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique 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.

Simplification of Choices: By breaking down the variety of cheeses into six categories, you make cheese accessible to all. This simplifies the cheese aisle so you can make confident choices. Personalized Approach: Not just a simple tasting but a personalized journey, allowing you to discover your preferences and feel more connected to your choices. Educational Component: The educational aspect enriches your understanding and appreciation, making you feel like experts by the end of the session. Engagement and Fun: The playful tone and interactive format create a lively atmosphere. This isn’t just a tasting; it’s an adventure filled with laughter and community. Practical Takeaways: A straightforward guide on how to shop for cheese and pair it with wine. Memorable Experience: Combining sensory enjoyment with personal discovery and social interaction makes for a memorable event. By weaving together these elements, your experience becomes a delightful and unforgettable journey!

Richmond, Virginia is celebrated for its over-the-top holiday lights displays every year—and this tour makes exploring them simple. In the evening, depart from Williamsburg via climate-controlled vehicle and travel to Richmond. You’ll learn all about the city’s history of tacky lights displays, will admire some of the best examples, and will even see the Christmas tree in front of the Virginia State Capitol.

What could be better than Christmas in Alexandria? On this six block, hour long walking tour, enjoy the festive decorations of this beautiful town while listening to a seasonal blend of Alexandria Holiday History and forgotten Christmas folklore. We're also bringing back the Victorian tradition of 'scary ghost stories by the fire', as your costumed guide ends the tour with haunted tales by lantern light in a historic graveyard. Don't miss this limited time only, seasonal event! Tours Run on the following dates: November 26, 28, & 29 at 8:00pm December 5, 13, & 20 at 8:00pm December 6, 14, & 21 at 7:30pm December 26 - January 1 at 7:00pm

Experience the top-rated brewery and meadery tour in Richmond, where you'll explore the city's best craft alcohol hotspots while enjoying tours and tastings included in your ticket! Operating year-round, this immersive experience takes you through Scott’s Addition, home to some of the region’s finest breweries, cideries, and meaderies. Led by expert guides, this USMC Disabled Combat-Veteran-Owned, women and minority-led tour brings you to Buskey Cider, Strangeways Brewing, Ardent Craft Ales, Black Heath Meadery, and Blue Bee Cider. At each stop, you’ll sample exceptional craft beverages while learning about the production process and the rich history behind each establishment. Whether you're a beer connoisseur, cider lover, or mead enthusiast, this tour is the perfect way to drink, learn, and explore the city. Perfect for private groups, bachelorette parties, and special events, this unique bar crawl lets you experience Richmond’s thriving craft scene like never before!