In contrast to the shiny modernity of Jackson-Triggs, Peller Estates offers old-world romance. The château has a peaked slate roof, dormer windows and a patio overlooking sprawling vineyards. A spacious ground-floor tasting room accommodates summer crowds, but serious samplers may want to seek out the reserve room upstairs, where the finest wines are kept. At the winery restaurant, chef Jason Parsons’ six-course dinner tasting menu ($115 per person with wine, $80 without) changes weekly. Find accommodation at the Inn on the Twenty (905-562-5336, 1-800-701-8074) or Olde Angel Inn (905-468-3411).