Celebrate Valentine's Day in Charlottesville (Updated 2026)

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 5-hour, private custom tour features 3 winery visits, luxury Sedan, tasting room recommendations, and an experienced personal Wine Trail guide. Add-on lunch options are...

Turn a day in Virginia wine country into a seamless experience. Our private wine & beer tours are designed for couples, small groups and anyone...

The Downtown Mall Food Tour is a unique and memorable way to visit one of America's top college towns....

Please join our knowledgeable, entertaining guides in an unparalleled tour of the best of food and culture on the world-famous UVA Corner....

A very comfortable and stylistic a tour and tasting some of Virginia’s finest vineyards and wines. It’s very private and enjoyable for couple looking for...

The Dairy Market is among Charlottesville's leading food, retail, and entertainment venues. Free parking is available onsite....

Cycle the gorgeous rural roads of Virginia's wine country. Visit two forward-thinking wineries and eat incredible locally sourced food. Learn about what ecological agriculture means,...

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...

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...

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...

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...

Charlottesville has experienced its fair share of turmoil and tragedy, alongside its charming streets and delectable cuisine. From the legend of the enigmatic Moon Ghost...

Skip the stress and confusion of finding a taxi upon arrival at the Charlottesville International Airport. Instead, book this private airport transfer service and enjoy...

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to...

Purchase one tour per car, not per person. Everyone listens together! Take a scenic drive through Virginia’s verdant wilderness with this self-guided tour. Stop to...

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,...

"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...