Cypress-lined road over golden Tuscan hills with a stone villa and infinity pool at sunset

Rome, Tuscany & Amalfi · Italy

An Italian Grand Tour

8 nights

Nine days that move from the marble grandeur of Rome to the soft golden hills of Tuscany and finish on a balcony above the bluest water you have ever seen. Built for families who want their children to feel the weight of history and the lightness of a long Italian lunch in equal measure.

Day 1

Rome, Arrival & a Soft Landing

A private transfer collects you from Fiumicino and brings you to Hotel de la Ville, a Rocco Forte property perched at the top of the Spanish Steps. Family suites are spacious enough for everyone to spread out, and the rooftop bar at Cielo has one of the great views in Rome. Tonight is intentionally unstructured, a stroll to Piazza di Spagna for the first gelato of the trip, an early dinner at Pierluigi for grilled fish and burrata, and to bed before jet lag wins.

Day 2

Ancient Rome, On Your Own Terms

A 7:30 AM private entry into the Colosseum before the crowds arrive, led by a family-focused historian who knows how to bring gladiators to life for an eight-year-old and a sullen fifteen-year-old simultaneously. From there, a slow walk through the Forum and Palatine Hill. Lunch at Roscioli, the kind of meal that converts skeptics into Italy lovers. The afternoon is yours: hotel pool, a nap, or an optional Vespa side-car tour through Trastevere as the light turns gold.

Day 3

The Vatican, Before the World Wakes Up

Early-access tickets to the Vatican Museums at 7:15 AM mean walking through the Sistine Chapel with perhaps a dozen other people instead of three thousand. Your guide is chosen specifically for families and will route you to St. Peter’s by way of the secret passages. After lunch at Armando al Pantheon, a hands-on gelato-making workshop near Piazza Navona that has rescued more than one tired afternoon.

Day 4

Into Tuscany, Casole d’Elsa

A private driver collects you mid-morning for the drive north through the Val d’Orcia, with a stop in Orvieto for lunch and the cathedral facade. By late afternoon you arrive at Castello di Casole, a Belmond hotel, a restored 10th-century estate on 4,200 private acres of vineyards, olive groves, and walking trails. Connecting suites and standalone villas both work beautifully for families. Dinner at Tosca, on the terrace, watching the hills go pink.

Day 5

Slow Tuscany

This is the day everyone secretly looks forward to. Morning pasta-making class with the hotel’s resident nonna, pici, hand-rolled, eaten for lunch. Afternoon by the infinity pool, or saddle up for a sunset horseback ride through the estate. For the grandparents, a private wine tasting in the cellar; for the teenagers, archery and mountain biking on property.

Day 6

Siena & a Truffle Hunt

A morning in Siena, the Piazza del Campo, the striped marble of the Duomo, a long lunch at Osteria Le Logge. Then on to a working truffle estate in San Giovanni d’Asso, where you and the kids will follow trained dogs into the woods, find your own black summer truffles, and shave them over fresh pasta at the farmhouse table. The drive home through the cypress-lined backroads is the postcard everyone hopes Tuscany will be.

Day 7

South to the Amalfi Coast

A private driver returns you to Rome for the high-speed train south to Naples, where a second driver continues along the coast road to Positano. Le Sirenuse is waiting, the pink and white grande dame above the harbor that has been welcoming families since 1951. Sea-view suites, the Champagne and Oyster Bar at sunset, dinner at La Sponda under 400 candles. Tonight is for doing nothing at all.

Day 8

Capri by Private Boat

Your gozzo, a classic Sorrento-style wooden boat, collects you from the Spiaggia Grande at 9 AM. The day is yours: the Blue Grotto if the swell allows, a swim into the Faraglioni rocks, an early lunch at Il Riccio with the chair you pull right up to the water. Back to Positano for an aperitivo on the hotel terrace and a quieter dinner at Lo Guarracino, set into the cliff path.

Day 9

Pompeii & Farewell

A morning with a private archaeologist at Pompeii, chosen because she leads tours for families and knows precisely which streets and houses will hold a child’s attention for two hours. Lunch at President in Pompeii (yes, a Michelin star steps from the ruins), and an afternoon return to Naples for your flight home, or extend with a final night in Sorrento at the Bellevue Syrene.

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