San Jose residents from left, Gianni and Janet Guerriero, Amanda Borges, and Mary and Rufino Borges enjoy a bottle of malbec wine with their picnic lunch just outside the tasting room Saturday at Castillo's Hillside Shire Winery in Morgan Hill.

If different varieties of wine were women, Nate Castillo might be considered a modern-day Cassanova.
The 26-year-old winemaker is just one member of the energetic family with diverse interests and talents that owns and operates Castillo’s Hillside Shire Winery, which is preparing to release new “upper echelon” higher-priced bottles and its first-ever Rosé, “Blushing Beauty” on the eve of its fifth anniversary.
Castillo, who obtained his second level sommelier certificate just a few years after the family accidentally fell into the wine industry, teaches private wine tasting classes (“like a dating site for wine”) at the winery that sits on a sharp slope in east Morgan Hill, and he often compares wine drinking to women and dating.
“My job is to help you figure out what you like. I’m cupid – I make a match,” Castillo said.
One of Castillo’s goals is to “destroy wine snobbery” and squash the tendency among some oenophiles to disparage others’ choices.
“You wouldn’t do that to someone’s girlfriend,” he said. “Don’t do that to someone’s (preferred) wine.”
Castillo’s Hillside Shire will mark its fifth anniversary in April. One way they plan to celebrate is with new art for their latest vintages’ labels, all of which are created by Nate’s sister Vivienne, 22. The labels feature his sister’s original art, depicting custom characters with Renaissance and fantastical themes with bright “popping” colors.
Vivienne, also a singer/songwriter, works as a music instructor for children at Youth Alliance in Hollister but can often be found at the winery’s tasting room on weekends serenading customers throughout the property’s impeccably manicured and ornamented grounds, which include a number of outdoor patios and views of Morgan Hill.
Mother Ronnie Jo Castillo, an accomplished opera singer in eight foreign languages (she and Vivienne toured Italy, including a performance at the Vatican’s high mass a few years ago), often joins her on vocals during these intimate performances.
Father Jess Castillo, a construction contractor, and older brother Michael, 29, can be found at the tasting room on the weekends but spend their days building homes for Jess’ company, Castillo Construction.
The family purchased the property at the end of East Main Avenue more than 12 years ago for their residence, Ronnie Jo said. They found out during the building and permitting process that the 12-acre property was under the state’s Williamson Act, which provides owners of farmland and open space with property tax relief in exchange for an agreement so that the land will not be developed for other purposes.
The Castillos were not farmers nor wine drinkers at the time, but they needed to make some agricultural income or face penalties or extra costs imposed by the state.
“We just decided to dig in and make the best of it,” Ronnie Jo said. So they decided to plant about six acres of vineyards, with the help of some established local growers.
A long driveway leads up to the Castillos’ manor-like residence, which stands out among the structures on the property. The quaint tasting room, guest house, outdoor kitchen and steep vineyards surround the family home.
Nate, who was “born and raised” in Morgan Hill with his siblings and studied kinesiology in college, was a ski instructor and massage therapist before diving in head-first as winemaker for the new family business.
Wine is where Nate found his passion.
“I’m in love with wine,” Nate said. He said he’s committed to becoming a master sommelier – the highest level that is rarely achieved worldwide. Later this spring, Nate will be working the soon-to-open Affina Bistro restaurant in Carmel as the house sommelier. In May, he plans to travel the vineyards of Spain, France and Italy to become acquainted with world-renowned winemaking regions.
While they were making wine, the Castillos figured they could produce a comfortable, relaxing vibe for visitors to the grounds, which also hosts weddings and other events for large groups. The Castillos noted they have seen complete strangers from distant areas become friends inside the tasting room.
“The world gets so small inside here,” Vivienne said. “It’s an open, inviting space. You’re coming to our house: You can hang out.”
Music has always strongly influenced all the Castillo family members. Nate is often seen pouring wine with a guitar strapped to his back, and Ronnie Jo said sharing those talents with visitors is another goal of the tasting room.
Castillo Wine Club members enjoy extended access to the grounds, discounts on bottles and “first dibs” on the latest vintages, Nate said.
The winery is not a member of the Santa Clara Valley Wineries Association and will thus not be participating in the March 29-30 Passport Weekend; however, it will be open for regular business.
Sheldon Haynie, past president of the association, hasn’t been to the Castillo property but is familiar with their wines.
“They’ve brought it to the (association’s) tasting committees, and it’s a pretty good wine,” said Haynie, who is the co-owner of Lightheart Cellars in San Martin. “They run a business successfully, and they have people that like their products.
Five of the Castillos’ 2008 vintages – including the Cabernet Franc and Petite Sirah – won medals at the San Francisco Chronicle Wine Competition. Their 2009 Port won a silver medal at the competition the following year.
In the coming weeks, Castillo’s Hillside Shire will be bottling new higher-end Cabernet Sauvignon and Petite Sirah, as well as a new Rosé, all produced from the Castillo estate’s vineyards.
“Now we’re focused on making the best wines we possibly can,” Nate said.

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