St. Peter’s Basilica rising beyond a stone bridge over the Tiber at sunset, Rome

Itinerary

Two weeks through Italy

Inspiration for your next adventure

Rome with a private guide, a week through Tuscany's wine country, and a few slow days in Florence. A trip built to be taken alone, with company exactly when you want it.

Who this is for

Someone traveling alone, on purpose. You want expert company on the days that call for it, plenty of time that is entirely yours, and long lunches at tables where eating alone feels completely normal.

The shape of the trip

Where you sleep, and the rhythm of the days

Rome, 5 nights · Val d'Orcia, 3 · Chianti, 3 · Florence, 2

Rome is the busiest stretch, with two guided days. Tuscany slows everything down, with a driver on tasting days. Florence is a soft landing before the flight home. The splurge is the private, first-entry Vatican tour.

Where to go and what to eat

The places

01 · 5 nights
Rome
Start with Bernini's Ecstasy of Saint Teresa and the three Caravaggios that hang in one chapel at San Luigi dei Francesi, free to anyone who walks in. Rise early for the Aventine Keyhole, with Saint Peter's dome framed inside it, then wander Trastevere. One morning goes to a private, first-entry tour of the Vatican Museums, the Sistine Chapel and Saint Peter's. Another day goes to a Roman art historian we trust, starting at San Clemente, where a staircase takes you down through two churches and a Roman house with a temple to Mithras. Finish with the Galleria Borghese on a timed two-hour visit, and the Colosseum and Forum late in the day, when the light softens.
02 · 3 nights
The Val d'Orcia
Drive or be driven about two and a half hours north into the valley of cypress lines and hilltop towns. Pienza, a Renaissance pope's ideal town, has pecorino and a view from its walls, and the Chapel of Vitaleta is at its best at golden hour. Give a day to Brunello in Montalcino, with a driver, and the Romanesque abbey of Sant'Antimo. Explore the cellars beneath Montepulciano, then spend an afternoon in the spas around Bagno Vignoni, a village whose main square is a steaming thermal pool, there to admire rather than swim in.
03 · 3 nights
Chianti
Stop in Siena on the way north for the Duomo and the Campo. In the Chianti hills, taste among the contemporary art installed around Castello di Ama, by appointment, walk the fortified village of Volpaia, and take a seat at the long shared table at Solociccia, Dario Cecchini's restaurant beside his butcher shop in Panzano. Eating alone is never lonely at that table.
04 · 2 nights
Florence
Return the car and finish on foot. See the Uffizi first thing and Michelangelo's David at the Accademia, then cross to the Oltrarno, where artisans still work in small shops. At six-thirty, climb to San Miniato al Monte to hear the monks sing vespers in Gregorian chant, then walk down to Piazzale Michelangelo as the city turns gold. Fly home from Florence, or take the fast train to Rome and the airport express, about two and a half hours in all.

My take on Italy

To truly experience Italy, a few smart choices set the tone for an unforgettable journey. Booking a private, first-entry Vatican tour transforms the experience - seeing the Sistine Chapel before the crowds arrive is like being in an entirely different room. When you're out exploring the Eternal City, having a guide makes all the difference; when you travel alone, a great guide is also fantastic company for the day, and Rome Art Stories with Luca is the absolute best choice (no, it's the ONLY choice). On wine-tasting days, hiring a private driver ensures you never have to choose between enjoying the wine and navigating the road.

Beyond the major sights, keep a few Italian customs in mind: embrace a slow-paced passeggiata (evening stroll) through the piazza, always stand at the bar for a quick espresso rather than paying for table service, and remember that shops often close in the afternoon for a midday break. For the ultimate photos, capture the sweeping Tuscan vistas from the rolling hills of the Val d'Orcia or the timeless golden hour light over Rome from the Pizzeria terrace at the Gianicolo.

As for what to skip, avoid trying to visit major museums on Mondays—places like the Borghese, the Uffizi, and the Accademia are all closed. You should also skip visiting in the summer, when much of Italy goes on holiday and Rome empties out and it will be blazing hot and not everyone has AC. Instead, aim for the sweet spots of late April to June, and October through November.

Above all, be prepared to come back and soon. Italy has a way of stealing your heart.

My take

Worth it, and what to skip

Worth it

The private, first-entry Vatican tour. The Sistine Chapel before the crowds is a different room.
A driver on tasting days. You never have to choose between the wine and the road.
A private guide in Rome. When you travel alone, a great guide is also great company for the day.

Skip it

Museums on Mondays. The Borghese, the Uffizi and the Accademia all close.
August. Not only are summers blazing hot, much of Italy is on holiday in August, and much of Rome with it. Late April to June, October to November are the sweet spots.