Travel Guide · Trip Inspiration
Where to Stay in Siena: Inside the Walls or a Villa in the Hills
A room above the Campo, or a villa with a pool and a view of the towers? How to choose, and the villas we know best.
The best place to stay in Siena depends on your group and your time. For two or three nights without a car, stay inside the medieval walls near the Piazza del Campo. For a week, or for a family or group, stay in a villa in the countryside 10 to 40 minutes from the city: Chianti to the north, the Val d’Elsa to the west, or the Crete Senesi and Val d’Orcia to the south. Doorways Villa Vacations, an Italian villa specialist since 1994, has personally inspected every villa in this guide.
Siena is the Tuscan city that stays with people. The shell-shaped Piazza del Campo, the striped cathedral, the brick lanes that tip downhill toward the countryside: our clients come home talking about it for years. The first question they ask us is where to sleep, inside the medieval walls or out in the hills where the city’s towers sit on the horizon. We have walked through every villa we offer around Siena, and for most families and groups our answer is the hills, with the city as your evening treat. Here is how to decide.
Should you stay inside Siena’s walls?
Staying in the historic center means waking to church bells, crossing the Campo for a cappuccino before the day visitors arrive and wandering back through quiet lanes after dinner. The center is compact and almost entirely car-free, and each of its 17 contrade, the historic neighborhoods that race in the Palio, has its own fountain, church and street-corner emblems to discover.
The trade-offs are space and logistics. Homes inside the walls are apartments and small hotels, often up several flights of stairs, and private gardens and pools are almost unheard of. Siena is also built on three ridges, so every walk is a gentle climb. For a couple or a two-night stay, it is magical. For a family reunion or a week with friends, most people want more room.
Why stay in a villa near Siena?
The country around Siena is some of the most beautiful in Italy: Chianti’s vineyards and woods to the north, the bare, rolling clay hills of the Crete Senesi to the southeast and the cypress roads of the Val d’Orcia farther south. A villa here gives you space, privacy, a pool and a long table outdoors, with the Campo a short drive away when you want it.
| Villa | Bedrooms / sleeps | Rate | Why we chose it |
|---|---|---|---|
| Villa Hortus Siena |
5 / 10 | From €12,000 / week From about €171 per person a night, €1,200 a week (10 guests, 7-night minimum) |
Ten minutes from Siena's walls, with a landscape-architect garden and a private wellness floor |
| Villa Collina Siena |
20 / 36 | Rates on request | A 13th-century estate 20 minutes from Siena, with tennis and a hilltop view of the city |
| Villa Montosca Siena |
10 / 20 | From €15,000 / week From about €107 per person a night, €750 a week (20 guests, 7-night minimum) |
Three houses on six acres west of Siena, each with its own kitchen |
| Villa Cardinale Siena |
8 / 16 | From €32,000 / week From about €286 per person a night, €2,000 a week (16 guests, 7-night minimum) |
A historic house on a wine and olive oil estate, 40 minutes south toward Montalcino |
| Villa Amarika Chianti |
7 / 14 | From €30,560 / week From about €312 per person a night, €2,183 a week (14 guests, 7-night minimum) |
A restored 1684 estate in the Chianti Classico hills near Castellina |
| Villa Colli Chianti |
7 / 14 | From €19,895 / week From about €203 per person a night, €1,421 a week (14 guests, 7-night minimum) |
Near Gaiole in Chianti, with a covered courtyard table for 14 and a pizza oven |
You can see them side by side, with photos and floor plans, on our Siena villas page. Traveling with a big group? See our large villas in Chianti and Siena for 16 or more guests.
Which area near Siena is best for a villa?
Each direction has its own personality.
North: Chianti
Between Siena and Florence, Chianti is the Tuscany of vineyards, stone villages and castle wineries. Castellina, Radda and Gaiole are 25 to 40 minutes from Siena, and Florence is within reach for a day too. Wine lovers should start with our guide to wine country near Siena.
West: the Val d’Elsa and the hills toward Volterra
West of the city, Colle di Val d’Elsa, Monteriggioni and the towers of San Gimignano are all close, and the countryside grows wilder and quieter toward Volterra. It is a wonderful base if you want Siena and San Gimignano in the same week.
South: the Crete Senesi and the Val d’Orcia
Head south and the landscape opens into the soft clay hills and lone cypresses that fill so many Tuscany postcards. The drive into Siena is longer, 40 minutes to an hour, but Montalcino, Pienza and Montepulciano are on your doorstep. Plan your days with our day trips from Siena.
How do you get to Siena?
The closest airports
Siena has no airport with regular passenger flights. The closest is Florence (Peretola), about an hour and a quarter by car, with connections through the major European hubs. Pisa is about an hour and 45 minutes away and has more direct flights within Europe. Flying nonstop from the United States, you will usually land in Rome (Fiumicino), about two hours and 45 minutes from Siena by car. If you are renting a car, pick it up at the airport rather than in a city center, to stay clear of traffic zones.
By train and bus
From Florence, the direct bus is often the easiest choice: it takes about an hour and a quarter and stops close to the center. Trains from Florence take about an hour and a half and arrive at Siena’s station below the city, which is linked to the upper town by a long series of escalators. From Rome, the simplest route is a fast train to Chiusi or Florence, then a regional train or bus to Siena, or a private transfer.
Can you drive and park in Siena?
Siena’s historic center is a limited traffic zone (ZTL) monitored by cameras, and fines arrive by mail, often months later. Your rental car’s GPS will happily lead you into it, so set it for a parking lot instead. The simple approach is to park in one of the public lots outside the walls, several of which are linked to the center by escalators, and walk in. If you are staying inside the walls, ask your host how to register your license plate before you arrive.
Uber is not a practical option in Siena. Taxis wait at a few ranks and can be called by phone, but there are not many, so book ahead for dinner and the ride home. If you are staying in a villa, you will want a car for day trips, or a private driver, which several of our villas can arrange for airport transfers, dinners in town and wine-tasting days.
Where should you stay for the Palio?
The Palio di Siena is run on July 2 and August 16, and the days before each race fill the city with trial runs, parades and outdoor dinners. Rooms inside the walls book up a year ahead. A villa within half an hour lets you drive in for the excitement and come home to a quiet pool. Read the Palio di Siena explained before you plan your dates.
So, inside the walls or a villa?
If you have a week, take a villa in the hills and come into Siena two or three times, once for the museums, once for an evening passeggiata and dinner, and once more because you will want to. If you have two nights and no car, stay inside the walls. Either way, tell us who is traveling and what you love, and we will match you with the right house. Talk to a Doorways advisor.
Still deciding when to go? Start with the best time to visit Siena.
Frequently asked questions
Is it better to stay inside Siena or in the countryside?
For a couple on a short stay without a car, a room inside the walls is lovely. For families and groups staying a week, a villa in the hills gives you space, privacy and a pool, with the Campo a short drive away for lunch and evening walks.
Can you drive into the center of Siena?
No. Siena's historic center is a limited traffic zone (ZTL) watched by cameras. Park in one of the lots outside the walls, several of them linked to the center by escalators, and walk in.
Where should you stay near Siena for the Palio?
A villa within 20 to 30 minutes of the city lets you drive in for the trial races and the race itself, then come home to quiet. Book a year ahead for July 2 and August 16.
What is the closest airport to Siena?
Siena has no airport with regular passenger flights. Florence is the closest, about an hour and a quarter by car, followed by Pisa at about an hour and 45 minutes. Nonstop flights from the United States usually land in Rome, about two hours and 45 minutes away.
How do you get from Florence to Siena?
The direct bus takes about an hour and a quarter and stops close to the center. Trains take about an hour and a half, and the drive is about an hour and a quarter.
Are there taxis or Uber in Siena?
Uber is not a practical option in Siena. Taxis can be booked by phone but are few, so we suggest a private driver for evenings out and airport transfers.
