Private Chauffeur Driven Greenhill Winery Tour Review

I won a weekday charter for a company celebrating a business milestone. We loaded up a group of middle-aged professionals from Southern Maryland and headed to Northern Virginia in the heart of Wine and Horse Country, Middleburg, Virginia. I’d heard it was pretty and people weren’t lying. I’d heard Jack Kent Cooke, owner of the Redskins (wish he still was) called it home and loved it there. 

The chauffeurs told us about the beautiful scenery and the great experience their wine tour clients had in Middleburg and other similar locations in and around the  Northern Virginia Wine and Horse Country. 

I met my wine tour group in Southern Maryland. The drive is a breeze when you’re in a fancy shuttle bus! From there we could enjoy the beautiful – it was like driving into a painting. Goodbye stress, hello peace and tranquility.



We visited a winery before heading to lunch at the prestigious Salamander Resort and Spa that was great. After lunch, we loaded up the Shuttle Bus, listened to some music and headed to Greenhill Winery.  I turned the corner on the tasting room building to be met with one of the most stunning picturesque landscapes I’ve ever seen. The double-decker patios gave way to a jaw-dropping 30-mile view filled with grapevines and green rolling hills.

The tasting room was light and airy with wonderful rustic furniture. Each handmade table has its own personality and own story. The natural light made you feel like you were outside. I heard that this Winery is one of Michelle Obamas’ favorite places and she’d often have cases brought in and served at important dinners and gatherings. I can see why!

The waitstaff and service and really made an impression on us corporate folks. So much so they canceled the next stop on the winery tour! By the end, dozens of group photos, Lots of high fives and hugs signaled to me that the Corporate Wine Tour was a complete success. We headed back to Southern Maryland without having to drive ourselves!

I was blown away by the Winery and Vineyards as you can tell! This is a place that you have to visit, see and experience to appreciate. From the wine to the views to the wine tour service, you won’t be disappointed!   ~ Bob S.

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