Casa Giacco is an apartment for four, restored from the centuries-old buildings of Castello di San Polo in Rosso, a medieval fortified estate in the hills above Gaiole in Chianti. This is an apartment on a historic medieval location, not a standalone villa, and it feels like one: vineyards on three sides, the 11th-century fortified church a few steps away, the estate's vineyards running down the slope. The pace is agricultural and unhurried.
If you want a pool and a private garden with no neighbours in sight, look elsewhere on this site. If you want to wake up inside the Chianti Classico zone with a glass of the estate's own wine on the table and Castello di Brolio visible on the next ridge, Giacco is the right choice.
The location is genuinely remote. You will need a car for everything, including groceries, and the nearest town of any size is Gaiole, ten minutes away. That suits plenty of guests well. For those wanting more space, Podere Castello and Borgo Castello are nearby properties on the same estate under the same ownership; a group could take two or three properties and still have private space within easy reach of each other.
Casa Giacco is listed under the following categories:
Casa Giacco is a two-storey apartment set within the historic buildings of the Castello di San Polo in Rosso estate, surrounded by vines and the oak-covered slopes typical of this part of Chianti. The apartment has been renovated to a practical, comfortable standard while keeping the terracotta floors and beamed ceilings that are traditional in Chianti farmhouses.
The two bedrooms sleep four, one is a double bedroom, the other a twin, both upstairs. There is one bathroom with a shower but no both. The kitchen is open plan and well equipped for self-catering. Inside dining and a separate outdoor table on the private garden both work for meals; the garden is sheltered and has views over the vineyard.
Castello di San Polo in Rosso is the fortified church you can see from the apartment. This remarkable Romanesque parish church dates to the 11th-12th century and was converted into a fortress during the 13th-14th century when it sat on the contested border between Florence and Siena. The three-nave basilica contains 14th-century frescoes attributed to the circle of Ambrogio Lorenzetti, portraying the life of Christ. The church is part of the private estate and is occasionally used for weddings and summer concerts. It's one of the most complete examples of a fortified church in Chianti.
Castello di Brolio is close by and worth an afternoon. This is where Baron Bettino Ricasoli created the modern Chianti Classico formula in 1872, defining the Sangiovese-led blend that became the regional standard. The Ricasoli family have held Brolio since 1141, making it Italy's oldest winery in continuous family ownership. Today you can tour the formal gardens, visit the museum dedicated to the "Iron Baron" (who was also Italy's second Prime Minister during the Risorgimento), and taste estate wines at the on-site osteria. The neo-Gothic structure you see was rebuilt by Baron Bettino in the 19th century, though the original fortifications date to the 11th century.
Castello di Meleto lies about 2 miles south of Gaiole. It may be even older than Brolio, built in the 12th century and considered virtually impregnable until an Aragonese army stormed it in 1478. The circular towers are characteristic of medieval Chianti defences. Today it's a winery and farm estate producing Chianti Classico, olive oil, and cured pork from Cinta Senese pigs. Daily tours include the ancient cellars.
Gaiole in Chianti (5-10 minutes by car) is the nearest market town, developed in the 13th century as a trading place and one of the three historic capitals of the Chianti League alongside Radda and Castellina. The pedestrianised Via Ricasoli has cafes, wine bars, and basic food shopping. Useful as a base rather than a destination in itself, though the market on Mondays is worth checking.
Badia a Coltibuono (about 3 miles north of Gaiole) is a deconsecrated Benedictine abbey with a Romanesque church, now producing good Chianti Classico. It's known for the cooking school founded by Lorenza De' Medici and the evocative ruins of the fortress of Montegrossi nearby.
Radda in Chianti (15-20 minutes) is one of the three historic "terzieri" of the Chianti League. The circular medieval centre and the Palazzo del Podestà, with its façade of carved coats of arms (former headquarters of the Chianti League for four centuries), are worth the short drive. Better restaurant options than Gaiole.
Siena is about 30-40 minutes south. The Campo, the Duomo and the warren of medieval streets make it an essential stop; if you're visiting in July or August, the Palio horse race fills the city and restaurants book up weeks in advance.
Florence is roughly an hour north (60-65km). The Uffizi, the Duomo, the San Lorenzo market and the view from Piazzale Michelangelo are all manageable as a day trip. Parking in the city centre is difficult; the Park & Ride lots outside the ZTL zone are a better option.
Wine tastings are everywhere in this part of the Chianti Classico. Beyond Brolio and Meleto, estates worth visiting include Castello di Ama (contemporary art installations within a working winery), Castello di Volpaia (a fortified village-turned-winery), and numerous family producers along the back roads. Ask us for recommendations based on your interests.
From € 201 to 345 per day
From € 1,405 to € 2,070 per week
Approximately
$ 1,644 to $ 2,422 in USD
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