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!

Reston Town Center is a hub of culture, dining, and entertainment, making your workshop a perfect addition to your plans. Whether you’re planning a date night, group activity, or just looking for something creative to do, your candle-pouring experience offers the ideal blend of fun and personalization.

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.

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.

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.

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.

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 vehicle to each destination. Enjoy guided tours of each vineyard, play indoor games, and purchase wine tastings, if you’d like.

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.

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.

Raise a glass with the spirits of the past on this haunted pub crawl through Colonial Williamsburg. Led by a costumed guide steeped in ghostly lore, you’ll explore historic taverns and haunted landmarks where tales of executions, scandal, and lingering souls still echo. Sip on local brews and cocktails as you uncover the chilling stories behind America’s colonial capital—perfect for those seeking a spirited night out with a supernatural twist.

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.

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.

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!

When you book a tour with, you get the leading tour provided within the the Monticello Wine Trail Region. Depending on group size, day of the week, our group can help get you access to some of the best tables at vineyards, guide you on dining options, and talk you through the history and landmarks of the area.

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!

Culinary Experience: Join Winemaker Donna for a Guided Lunch Featuring: Five categories of wine Tapas-sized food pairings Three delicious entrees A cheese course with three exquisite cheeses Three delightful desserts Three decadent chocolate delicacies Highlights: Learn how to achieve perfect pairings every time Discover the nuances of wine Experience enlightening 'aha' moments for social gatherings Come hungry for a deliciously educational meal!

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!

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.

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.

Enjoy the evening cruising the back bays of Chincoteague on our one of a kind double decker party pontoon boat, taking in the breathtaking wildlife and beautiful waters as the sun sets over Wallops Island! Our team is here to make sure you’ll have an unforgettable and safe adventure on the water! Book now to reserve your boat!

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

Beneath the opulent veneers of Richmond's gilded age architecture and the day-to-day life of academia, bubble tales of chilling haunts, macabre murders, and bizarre paranormal activity. Join us for a spooky stroll around the Monroe Park campus as we explore stories that are often left out of your typical college brochures. Cloaked in the shadows of the beautiful and historic neighborhood, this tour includes the following spirited tales: The grim history of Monroe Park that lies hidden under the well-tended landscape of today, a hospital-turned-student dorm that still houses the spirits of long-departed patients, the ghosts of a landmark theater, and more... Your Guide will share with you the history of the neighborhood, and how it relates to the tales of the mysterious and tragic things that have led to numerous reports of paranormal activity along the tour route.