Among the countless memorable travel experiences the world offers, a certain number of them can be classed as truly great. A Tuscan driving tour is one such experience. The region draws me back again and again. Roads thread a rolling countryside of vineyards, olive groves and pastures punctuated by cypress allées, ancient hill towns, stone farmhouses and the occasional castle. Although some of the byways are narrow, few are nerve-wracking or poorly maintained, and each bend seems to present a view that’s better than the last. A road trip here offers great variety — wine, food, history, art — and just as important, there are numerous well-serviced and character-rich places to stay.

On my most recent trip to Italy, I discovered four delightful new resorts and tested three previously recommended properties. No one would want to follow such an itinerary on a vacation, but my five favorite hotels of the trip could be strung together into a sensational two-week journey encompassing some of the best of Tuscany and Umbria. Of course, it would also be possible to have a wonderful time at just two or three of them, perhaps in combination with Florence. One of our Italy experts in the Travel Office can help you put together an itinerary that’s precisely right for you.