Customized transportation solutions since 2008

From wineries to weddings, celebrations to nights on the town, we'll take you there.

Versatile Tours & Custom Rides

  • Winery and brewery tours

    Explore the scenic vineyards of King Family Vineyards and Valley Road Vineyard. Indulge in the flavors of handcrafted beers at Devils Backbone and Pro Re Nata. We are experts in designing tailor-made itineraries that can take you to these and other breweries and wineries.

    One of the vineyards that Baileys Retreat Tour Co provides winery tours is Trump Winery, located in Albemarle County outside of Charlottesville and Crozet.

  • Historic and scenic trips

    Take a step back in time with a visit to Monticello and Michie Tavern to learn about the legacy of Thomas Jefferson and immerse yourself in the charming colonial atmosphere. Enjoy the picturesque views on The Skyline Drive or The Blue Ridge Parkway, or explore an orchard and delight in the fresh fruits of Albemarle County.

    Baileys Retreat Tour Co offers tours and transportation to Monticello, Michie Tavern, Mount Vernon, and other historic locations in and around Charlottesville, Crozet, and Albemarle County.

  • Tailored transportation

    Looking for a reliable transportation partner for your next night out in downtown Charlottesville, a birthday excursion, or a wedding? Look no further. You don't need to depend on rideshares anymore when you have us. We can plan a custom trip to take you wherever you need to go, without any headaches.

    Baileys Retreat Tour Co offers customized transportation options for small groups to weddings, downtown Charlottesville, and other locations around Albemarle County, Virginia.

What People Are Saying

“The absolute best! If you wanna relax with your girlfriends or take a family trip, do not waste another second, book these guys for your winery hopping day!”

— Katya L.

“This tour was the best! Host was outstanding. Great way to go wine tasting. He took us to some beautiful wineries and we saw some beautiful country. Worth every penny!”

— Carl F.

“Billy was very knowledgeable and curated the stops just for us. We knew we were destined to have a great day. All of our spots were great and we loved every part of the experience.”

— Alexis J.