There is nothing quite like Central Italy. With its medieval fortified villages and ochre-coloured villas, set within a landscape of vineyards, cypress trees and hills rolling down to the coast, it is little wonder the region charms everyone who visits. But this bountiful, picturesque part of the world would take donkey's years to explore properly, so let us admit from the outset that this is not a tourist guide. Even with the greatest will in the world, you will never see all the sights, linger over every piece of art and potter about each beautifully preserved hilltop town. Hard decisions had to be made, and we duly made them.
What we have, instead, is a driving route built around the idea that five days is the ideal time to spend on the road without becoming cramped or restless. We have not confined you to Tuscany, either. We start in Lazio, head through Toscana and Liguria, and bring things to a close in Lombardia, uncovering splendours, staying at fantastic hotels, eating exquisite food and enriching the soul through culture, romance and luxury along the way. In short, it is the good life. The starting point is Rome, which is no coincidence: you will have a far wider choice of rental cars there than at any other Italian airport. Strangely, for the capital, Rome also has a terrible airport, so collect your luggage, deal with the paperwork and hit the road fast.
The drive from Rome to the Castello di Casole, near Siena, takes under three hours, ending on the historic dirt roads that sweep across the voluptuous hills of Tuscany. Nothing, however, prepares you for the majesty of the place itself: a tenth-century hamlet turned hotel and serviced residential community, centred on a charming castle dating back to 998 and once owned by the film director Luchino Visconti before it fell into aristocratic ruin and required seven years of renovation to resurrect. Opened in 2012, the American-owned private estate spans some 1,700 hectares and offers 41 generously sized suites, serviced villas and farmhouses, two restaurants, a vaulted spa set within the castle's former wine cellar, a fitness centre, an infinity pool, an ancient chapel and a yoga pavilion. With service geared towards the international traveller, it is a wonderful place to escape the humdrum of ordinary life.
Day two runs from Siena to Florence. Check out early to make the most of both, and have the concierge reserve lunch at the Taverna di San Giuseppe, a Sienese institution housed in a building that dates to 1100, with a tufa-rock wine cellar from 200 BC. Siena itself, a Roman settlement of the first century BC, is a real gem: begin at the shell-shaped Piazza del Campo, take in the Palazzo Pubblico with its Torre del Mangia and the Banca Monte dei Paschi, the oldest surviving bank in the world, then walk to the thirteenth-century Duomo. An hour's drive brings you to Florence, for centuries a melting pot of creativity and commerce that delights shoppers and culture-vultures alike. There are grander hotel names, but the best is a quieter one: Portrait Firenze, part of the Ferragamo family's Lungarno Collection, overlooking the Ponte Vecchio, with just 36 rooms that feel more like ultra-chic apartments than suites. Book dinner at Trattoria Cammillo, a haunt of the Florentine cognoscenti since the 1940s.
The third day heads to Forte dei Marmi by way of Pisa, where it is worth chalking off the Leaning Tower, one of the Seven Wonders. Forte dei Marmi, meaning marble fort, exists because in the sixteenth century Michelangelo built a road to bring Carrara marble down from the Apuan Alps to the coast. Over time it became a low-key bolthole for moneyed Italians; Zucchero, Armani, Andrea Bocelli and the Agnelli family all own houses here. Do not expect an Italian Saint-Tropez, but rather spaced-out low-rise buildings shaded by pines, a wide darkish-sand beach and a topography so flat that everyone gets about on bicycles. The Principe Forte dei Marmi, opened in July 2010, is the most stylish boutique hotel in the area, its pared-down decor harmonising warm woods, stone and glass across 28 rooms, with an award-winning spa and the hotel's own baby-blue bicycles for pedalling into town. Dinner belongs at Bistrot, the area's Michelin-starred hotspot.
Day four is the one to savour. The drive from Forte dei Marmi to Portofino takes less than an hour and a half, passing through Rapallo and Santa Margherita Ligure. Arriving by car, rather than boat, gives a fresh perspective on the fishing port, and a stay at the Belmond Hotel Splendido, a former Benedictine monastery, a better one still. Part of the former Orient-Express group since 1985, the Splendido has stayed in the top flight of European hotels since 1902, hosting everyone from Bogart and Bacall to Brando and Spielberg across its 64 rooms. Spring for a light, airy Junior Suite, and do not miss the breathtaking manicured garden of daisies, roses, jasmine and ancient olive trees. For lunch, try Puny in the harbour, where the octogenarian owner Luigi Miroli claims his pappardelle alla portofino is the best pasta in the world. He is not, it turns out, exaggerating. Dine on the candle-lit terrace, La Terrazza, where the fish specialities are the highlight.
The final leg runs to Milan, two and a half hours away if you resist the designer outlets en route. Even amid so many great hotels, we still love the Four Seasons, a former fifteenth-century convent transformed into an urban sanctuary by Aman's Adrian Zecha, who flew the Regent flag there until the Four Seasons acquired it in 1992. Enjoy your last night. Over five days and roughly 1,100 kilometres, it is hard to beat this holiday for freedom of movement, comfort, luxury, food and sheer happiness. For now, this is tops.
