Inspired by his grandfather’s legacy of superior wine crafting, Harry Robibero took the first step in rebooting the family tradition by buying 42 acres of property in the Hudson River Valley with his wife Carole in 2003. He couldn't start harvesting any grapes just yet, however—there was already an operational winery on the premises. He bided his time, waiting for the opportunity to fill his home's glasses and well-concealed flasks with his own cask-aged creations. In 2007, the original winery announced that it was vacating the acreage, opening the door for Harry to finally cut the ribbon on his family's very own vino haven.

After years of revamping the property, the family now welcomes visitors to savor red and white artisan wines by the bottle or glass while playing board games, watching sports on the 52-inch TV, warming up by the indoor fireplace, or listening to music during one of the winery's weekly events. The Robiberos also helm tasting sessions, in which oenophiles can sample a lineup of their expertly handcrafted libations. During the warmer months, they open the outdoor patio so that their guests can sip on sangria or wine while overlooking the lush vineyards speckled across the fertile valley.