Follow a winding country road past hillside vineyards to an ivy-covered stone barn: welcome to California's finest private contemporary-art collection and acclaimed winery (hessperssonestates.com; tastings from $85 incl museum, museum walk with director $110). Head upstairs to galleries brimming with thought-provoking installation art, starting with Leopoldo Maler's 1974 burning typewriter – an homage to his uncle, a newspaper editor killed by Argentina's junta. Highlights include Anselm Kiefer's lead-lined bunker made of shingles from collapsed Cologne Cathedral, and Andy Goldsworthy's curtain of thorns loosely held together by gravity – a delicate work that miraculously survived Napa fires.
Enter the side barn door, where winery staff point you upstairs, past the spooky barrel room. For insights on the artists and their work, download the free audio tour on Hess Collection's website. Reserve ahead for a guided tour (10:15am daily, $50). The galleries are free to visit, and leave you with much to discuss in the downstairs tasting room. Napa cabs are a given, but Viognier is the scene-stealer here (bottles $30 to $100). In summer and fall, enjoy wine and cheese pairings in the sunny, wisteria-fringed sculpture garden ($55 for two). Estate tours come with sweeping hilltop vistas, plus farm-to-table meals featuring ingredients from Hess' own organic gardens (lunch 11am, $165; dinner 5pm, $215). Hess' winery gift shop is Napa's most tempting, featuring art books, wine accessories, and locally designed statement jewelry.