On this occasion, begin in Florence, with its innumerable artistic treasures, its extraordinary cast of historical characters, its effortless style and its exceptional food and wine. Because the historic center can be crowded, I often base myself at Belmond’s Villa San Michele, a short drive above the city, in Fiesole. (The hotel runs a regular shuttle service to and fro.) The view of the city’s skyline from the terrace, dominated by Brunelleschi’s great cathedral dome, is breathtaking. Dip into town during the day and retreat to this oasis each afternoon.

Rent a car (or hire a driver) and head into the heart of Tuscany, stopping for lunch in Siena. Continue south to the hilltop Rosewood Castiglion del Bosco, which has plush, classic décor and a dramatic infinity pool. It’s close to the lovely hill town of Montalcino and superb Brunello wineries such as Il Poggione and Podere le Ripi.

Turn east, pausing to see the Renaissance jewel box of Pienza. Continue just over the border into Umbria to the impressively chic Castello di Reschio. In addition to fine restaurants, it offers a sculptural pool, a seductive candlelit cellar spa and world-class stables. If you can tear yourself away from the estate, which is difficult, the exquisite walled town of Urbino (the birthplace of Raphael) lies a 90-minute drive to the northeast.

After a couple of days of relaxation, drive south via Assisi to Rome. (If you have a rental car, consider dropping it at the airport and taking a taxi into town to avoid the hassle of Roman traffic.) Italy’s capital has several fine hotels, but the classic is Hassler Roma, atop the Spanish Steps, owned by the Wirth family since 1964. The view from the sixth-floor panoramic Michelin-starred restaurant is unforgettable. [Discover more articles on Rome that include information about restaurants, cooking classes, ancient sites and Vatican touring strategies.]

After three or four days, head south to the Amalfi Coast, one of the most sensationally scenic places on the planet. Base yourself first in Positano at Le Sirenuse, owned and run by the Sersale family since 1951. From the dining terrace or your room’s balcony, you can gaze at the glorious jumble of multicolored buildings plunging down to the Mediterranean. Day trips to Capri and the ruins of Pompeii are easy to make from here.

You could happily end your journey in Positano, but it does seem a shame to miss Belmond’s Caruso, perched on a cliff in Ravello some 1,000 feet above the sea. Its terraced gardens and sublime horizon pool both offer stupendous panoramas of the Gulf of Salerno. A shuttle takes guests to and from Amalfi and Positano, and a private boat is available for excursions. But Caruso is really a place to relax and read, all the while marveling at one of the most beautiful resort settings in the world.