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Frequently Asked Questions
How do I get to Tuscany?
Fly into Florence (FLR) or Pisa (PSA) from a major European hub, or into Rome Fiumicino (FCO) and drive north. Most US flights connect through London, Paris, or Amsterdam.
Is Tuscany good for a wine-focused trip?
One of the best in the world. Brunello di Montalcino, Chianti Classico, and Vino Nobile di Montepulciano are all within a short drive of each other. The estates are largely family-owned and still personal.
When is the best time to visit Tuscany?
May and September. The weather is excellent, the fields are at their most photogenic, and the tourist numbers are manageable compared to summer.
Should I base myself in Florence or the countryside?
The countryside. Florence is worth two or three days but the Tuscan experience is in the landscape, the estates, and the slower pace of the Val d'Orcia. Treat Florence as a stop, not a base.
5-Day Itinerary
This route is built around the countryside south of Siena rather than Florence. It moves slowly and eats well.
Day 2
Val d'Orcia to Montalcino
Where to stay:
Rosewood Castiglion del Bosco
What to do:
Drive the Val d'Orcia, private vineyard lunch, check into the estate
Day 1
Siena
Where to stay:
Hotel Certosa di Maggiano
What to do:
Arrive, walk Piazza del Campo at sunset, dinner at Osteria Le Logge
Day 3
Castiglion del Bosco
Where to stay:
Rosewood Castiglion del Bosco
What to do:
Morning truffle hunt or horseback ride, afternoon pool, dinner on the terrace
Day 4
San Gimignano and Volterra
Where to stay:
AdAstra or return to the estate
What to do:
Morning San Gimignano, afternoon in Volterra, views over the Cecina valley
Day 5
Chianti to Florence
Where to stay:
Depart from Florence
What to do:
Drive north through Greve and Radda, lunch in the Chianti hills, Florence evening flight
Want the Full Version?
This itinerary gives you the shape of the trip. The hotel bookings, restaurant reservations, private guides, and transfer logistics are where the difference is made. Reach out and we will put it together for you.
Don't Miss!
A private wine lunch at a small Brunello estate outside Montalcino. Brunello di Montalcino is one of Italy's finest red wines and it is produced by a handful of families on a small plateau above the Val d'Orcia. The best lunches here happen in working cellars, paired to whatever was opened that morning, with local black pork and Pecorino from the valley. This requires a connection. It is exactly the kind of thing a good travel advisor arranges.
Top Attractions
What to See and Do
Val d'Orcia: the UNESCO-listed landscape south of Siena. The rolling hills, the cypress rows, the unpaved strade bianche: drive it in May when the wheat is green or September when the light turns amber.
Private Brunello vineyard lunch at a small Montalcino producer: not a tasting. A full seated lunch at a working cantina, with the winemaker or estate family. This is arranged in advance and is not available on booking sites.
San Gimignano and Volterra: two medieval hilltop towns within an hour of each other. San Gimignano for the towers and the saffron gelato. Volterra for the alabaster workshops and the complete absence of tour buses.
Booking through a Fora-affiliated advisor unlocks perks that are not available at the standard rate. No extra cost to you.
01
Rosewood Castiglion del Bosco, Montalcino
A private Brunello wine estate in the Val d'Orcia, with its own vineyard, village, and golf course set across 4,200 acres of protected Tuscan landscape. One of the most complete estate experiences in Italy.
Fora Perks:
Breakfast daily
resort credit
upgrade on arrival
vineyard access and private picnic
02
Belmond Castello di Casole
A 10th-century castle converted into a luxury hotel at the centre of a 4,200-acre private estate in the Chianti hills, midway between Siena and Volterra. Dramatic position, excellent cooking school.
Fora Perks:
Breakfast daily
$100 hotel credit
upgrade
welcome amenity
cooking class access
03
AdAstra, San Gimignano
A small Relais & Chateaux property in the hills outside San Gimignano, with an organic farm, a pool overlooking the valley, and a kitchen that takes the local produce seriously. Quiet and genuinely personal.
Fora Perks:
Breakfast daily
room upgrade
welcome amenity
flexible check-out
Luxury Hotels
Where to Stay
Tuscany
Tuscany is one of the most visited regions in Europe and one of the most misunderstood. The majority of visitors base themselves in Florence and do day trips. The better version is the opposite: base yourself in the Val d'Orcia or the Chianti hills and treat Florence as the day trip. The landscape south of Siena, the Brunello wine country around Montalcino, the medieval hill towns that have barely changed in five centuries: this is the Tuscany that earns the reputation.
When to go
Best time to visit
Peak Season
June, July, and August. Beautiful but hot and crowded, especially in Florence and the Cinque Terre.
Sweet Spot
May or September. The wheat is green in May and golden in September. Both months are ideal for driving and eating outdoors. October is the harvest season for grapes and olives. The countryside is at its richest and the local food is at its best.