Medieval Tuscany
The Campo in shadow, the Crete Senesi rolling south, and dinners under pergolas in deep Chianti country.
Siena is the medieval city that did not become a Renaissance one — and is more beautiful for it. The Campo, the Duomo, the Torre del Mangia, and a centro storico unchanged since the 14th century.
Stay in a villa in the Crete Senesi just south of the city — the soft, sculpted clay hills that look like an Andrew Wyeth painting — or up in the Chianti Senese northeast. Both put you twenty minutes from the Campo and an hour from Florence.
Best Villas
Siena
5 Beds·5 Baths·10 Guests
From €12,000 / week
Siena
6 Beds·5 Baths·12 Guests
From €12,145 / week
Siena
7 Beds·7 Baths·12 Guests
From €14,450 / week
Siena
8 Beds·7 Baths·16 Guests
From €32,000 / week
Siena
10 Beds·11 Baths·20 Guests
From €25,000 / week
Siena
20 Beds·20 Baths·36 Guests
Rates on request
Experiences
The Palio runs July 2 and August 16. If you're not in town those days, the trial runs in the days before — and the contrada dinners in the streets — are spectacular and far more accessible.
The cathedral floor uncovered (mid-August through mid-October), the Piccolomini Library frescoes, the Pisano pulpit — all to yourself with a guide.
Forty-five minutes south. Pienza for pecorino, Montalcino for Brunello, the cypress-lined road to Monticchiello — the postcard image of Tuscany.
Pici hand-rolled one by one, pappardelle al cinghiale, panforte, the long lunch.
Forty-five minutes south to Montalcino. The Brunello producers that defined the style — Biondi-Santi, Casanova di Neri, Soldera, Argiano.
Monte Oliveto Maggiore for the Sodoma and Signorelli frescoes, Sant'Antimo for the Gregorian chant.
Travel Advisor
From the right villa to private chefs, boat charters, and bespoke experiences, we take care of every detail.
Beyond the Villa
Forty-five minutes south to the UNESCO landscape — pecorino at Pienza, Brunello at Montalcino, Vino Nobile at Montepulciano, lunch at La Porta in Monticchiello.
Ninety minutes northwest. The towered town of San Gimignano in the morning, lunch with a saffron pasta, Volterra's alabaster workshops in the afternoon.
An hour by car or train. The Duomo, Uffizi, lunch in the Mercato Centrale.
Forty-five minutes north into the Chianti Classico zone — Castellina, Radda, Gaiole — wineries and lunches.
An hour east. Frances Mayes country, lunch on the piazza, Etruscan museum.
An hour northeast. The Piero della Francesca fresco cycle, the antiques market on the first Sunday of each month.
Climate
| January | February | March | April | May | June | July | August | September | October | November | December |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 49°F | 52°F | 58°F | 64°F | 71°F | 79°F | 85°F | 85°F | 78°F | 67°F | 56°F | 50°F |
Source: long-term monthly averages for the region. Sea temperatures stay comfortable for swimming May through October.
Where it is
Travelers Ask
Siena is the medieval rival of Florence that lost the rivalry and was preserved by it. The Republic of Siena fell in 1555 and was effectively frozen — no Renaissance rebuild, no baroque overlay, just a 14th-century city in red-and-pink brick.
The Campo is the most beautiful piazza in Europe — a shell-shaped slope flowing down to the Palazzo Pubblico, where the Palio horse race is run twice each summer (July 2 and August 16) and where most of Siena eats lunch the rest of the year. The Duomo is a Romanesque-Gothic black-and-white marble masterpiece, with the floor uncovered (twice a year) to reveal the Beccafumi and Pinturicchio inlays. The Torre del Mangia is the only secular tower in Italy taller than its city's cathedral.
Around Siena is the most beautiful Tuscan landscape — to the south, the Crete Senesi (the eroded clay hills with their tiny cypress-topped knolls and their sculpted ridgelines); to the southeast, the Val d'Orcia, the most photographed valley in Italy; to the north, Chianti Senese, the southern half of Chianti Classico. A villa in any of these is the trip.
The food in Siena is medieval-and-Tuscan: pici (hand-rolled noodles), pappardelle al cinghiale (wild-boar ragù), ribollita, pici cacio e pepe, panforte (the spiced fruit-and-nut cake, around since the 13th century), ricciarelli. Restaurants: La Taverna di San Giuseppe, Osteria Le Logge, Bar il Palio on the Campo for lunch, Antica Osteria da Divo, La Pasta Fresca.
May, June, and September are our favourite months. The Palio runs July 2 and August 16 — if you want to be in Siena for it, plan a year ahead. April is beautiful in the Crete Senesi (wildflowers). Late September and October are the vendemmia, beautiful and quiet.
Siena has the same inland Tuscan climate as Chianti — hot dry summers and cool damp winters. Monthly highs from around 49°F in January to 85°F in July and August. Pool weather mid-May through late September. The city itself stays cool in summer because of the stone and the hills.
The Palio runs twice each summer — July 2 (the Palio di Provenzano) and August 16 (the Palio dell'Assunta). If you want to be in Siena for it, plan well ahead — accommodation in the centro storico sells out a year in advance. The trial runs in the days before, and the contrada (district) dinners in the streets, are spectacular and almost as good.
Pici (hand-rolled noodles) with cacio e pepe or wild-boar ragù, pappardelle al cinghiale, ribollita, pici all'aglione, panforte, ricciarelli, cantucci with vin santo. Our favourites: La Taverna di San Giuseppe, Osteria Le Logge, Antica Osteria da Divo, Bar il Palio for lunch on the Campo.
A private Duomo and Piccolomini Library visit, the Campo at golden hour, the climb up the Torre del Mangia, the Pinacoteca Nazionale, a Brunello tasting at Montalcino, a Val d'Orcia driving day, a Crete Senesi morning at the Monte Oliveto Maggiore monastery, a cooking class with a Senese nonna.
The Val d'Orcia (45 min south), Montalcino and Montepulciano for the wines, San Gimignano and Volterra (90 min northwest), Florence (1 hr), Chianti (45 min), Cortona (1 hr east).
The centro storico is a limited traffic zone (ZTL) and entirely walkable. For day trips and for staying in the surrounding hills, a car is essential, or arrange driver service through our concierge.
Explore
Each region is hand-picked, walked, and slept in by us first. See which one is calling.
“A fabulous experience in every way. Thank you for all your help in working with us to choose the perfect villa and for all the recommendations. A trip to remember.”Doorways Client · Villa Larianella
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“Villa Mida is a delightful surprise — amazing water views, a unique indoor spa, attentive staff. After full days exploring the Amalfi Coast it was wonderful to return to a soothing setting to recharge. We can’t wait to return!”Doorways Client · Villa Mida
“This villa was amazing — everywhere you looked was a “wow” moment. Pool, hot tub, outdoor kitchen, king-size beds with double shower heads. Bocce, foosball, ping pong. Thanks Susan for recommending this property for the four couples.”Doorways Client · A Tuscan Villa
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“10/10 would highly recommend. Susan is the utmost professional, full of knowledge, and she really gets to know you. Her trip planning and the details she provides are very valuable. A must if you want a unique and tailored experience!”Doorways Client · Doorways Client
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“Comfortable in every way — and the chef was outstanding. Walking, eating, exploring… just entering into the beauty and culture of Italy.”Doorways Client · Casa del Fattore
