San Ysidro Ranch, A Rosewood Resort

No wonder this was JFK's honeymoon spot: The 500-acre property, which got a $150 million re-investment in 2011-2012, gives the impression of stretching on forever (even if a few neighboring mansions creep into the picture), and when you arrive at the long driveway lined with olive trees and lavender, you have the sense of being on the frontier, at the last citrus grove before civilization gives way to the scrubby Santa Ynez Mountains. In addition to the 27 rooms in the main house, most of the 14 vine-covered cottages have decks and hot tubs and the resort sits just an hour south of the Santa Ynez Valley, a perfect daytrip for wine tasting.