California Road Trip: Testarossa Winery

by Rob | May 2, 2026 | Road Trips

California Road Trip: Starting Our New Orleans Morning

California Road Trip: Starting Our New Orleans Morning

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From Santa Cruz to a Family Celebration at Testarossa Winery

After spending the morning exploring California’s beautiful coastline, we returned to the Residence Inn San Jose Campbell to get ready for one of the main reasons for our cross-country journey—our nephew’s wedding. Once dressed for the occasion, we made the short drive to Testarossa Winery in the charming town of Los Gatos. Nestled in the foothills of the Santa Cruz Mountains, the winery provided a beautiful and elegant setting for such a special family celebration.

Testarossa Winery combines award-winning wines with a fascinating history that dates back more than a century. Although the Testarossa label was founded in 1993 by Rob Jensen and Diana Jensen—who began making wine as a hobby in their Silicon Valley garage—the winery is housed in the historic Novitiate Winery in Los Gatos. The original stone winery was built in 1888 by Jesuit Fathers and Brothers from Santa Clara College (now Santa Clara University) to produce altar and fortified wines for the seminary. Wine has been continuously produced at this location for well over a century, making it one of California’s oldest continuously operating wineries.

Walking through the beautiful stone buildings and landscaped grounds, it was easy to appreciate the blend of California history and modern winemaking. The original cellars, historic architecture, and peaceful courtyards created an unforgettable atmosphere for the wedding ceremony and reception. Whether you are visiting for a wine tasting, a private event, or simply to explore its rich history, Testarossa Winery offers a unique experience that reflects both California’s winemaking heritage and the innovation of Silicon Valley.

Watching our nephew begin this new chapter of his life in such a beautiful setting made the day even more meaningful. Surrounded by family, friends, and the timeless charm of Testarossa Winery, it became one of the most memorable moments of our entire Florida-to-California road trip. Even if you are not attending a special event, Testarossa Winery is well worth a visit for its outstanding wines, remarkable history, and one of the most picturesque settings in the San Jose and Los Gatos area.

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California Road Trip: Testarossa Winery

Celebrate a special family occasion at Testarossa Winery, a historic winery nestled in the foothills of Los Gatos, California. Housed in the original 1888 Novitiate Winery built by Jesuit Fathers and Brothers, Testarossa blends California’s rich winemaking heritage with…

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