Siena is easily accessible from Pisa Airport and from here a transfer is included to Gaiole in Chianti, which is around 40 minutes’ drive.
What better way to begin this trip than staying at a 5-star hotel in a former castle overlooking the Tuscan countryside. Free time on arrival to relax by the pool and settle in, and perhaps to sample your first glass of the world-famous red wine, Chianti Classico, which the region is famous for.
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Overnight Gaiole in Chianti
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Accommodation
A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.
This exquisite 5* hotel is set in an ancient monastery from the 10th century. The large bedrooms have traditional Tuscan décor and panoramic views over the valley or the courtyard, and they have WiFi access and air conditioning. The outdoor pool has a waterfall and a sun terrace to sunbathe and relax on. It’s Il Pievano 1* Michelin restaurant is situated in the castle’s historic hall and offers a large wine list from the wine cellar. Candlelit dinners are also served out on the courtyard if preferred. Wine can be purchased from their shop to take home as a souvenir. There’s also a gym, tennis courts, table tennis, billiards room, heated indoor pool, sauna, tepidarium, Turkish bath, emotional showers, and spa treatments available (additional charges apply and advance booking is recommended).
After breakfast there’s an included transfer to Radda in Chianti. After taking time to explore this medieval wine town, perched on a hilltop, and surrounded by the stunning landscapes. Commence the walk back to Gaiole in Chianti which goes through a range of scenery including a dense concentration of vineyards, olive groves, orchards, terraced slopes, and wooded valleys.
Reach Vertine, a hamlet with a castle and medieval walls. Inside these walls is the Church of San Bartolomeo a Vertine, dating back to the 11th century with Renaissance frescoes by the Florentine School inside. Vertine also has a winery, so there’s the opportunity to stop for a tasting.
Walking downhill into Gaiole in Chianti and back to the hotel. Sample an included dinner tonight in its 1* Michelin restaurant.
Ascent/Descent: 359m/527m
Please note that the Michelin star restaurant closes normally around the 22-Oct, so if you are arriving later than this, the dinner tonight, won't be included.
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Overnight Gaiole in Chianti
![]()
Accommodation
A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.
This exquisite 5* hotel is set in an ancient monastery from the 10th century. The large bedrooms have traditional Tuscan décor and panoramic views over the valley or the courtyard, and they have WiFi access and air conditioning. The outdoor pool has a waterfall and a sun terrace to sunbathe and relax on. It’s Il Pievano 1* Michelin restaurant is situated in the castle’s historic hall and offers a large wine list from the wine cellar. Candlelit dinners are also served out on the courtyard if preferred. Wine can be purchased from their shop to take home as a souvenir. There’s also a gym, tennis courts, table tennis, billiards room, heated indoor pool, sauna, tepidarium, Turkish bath, emotional showers, and spa treatments available (additional charges apply and advance booking is recommended).
This loop walk out of Gaiole in Chianti reveals the variety of Chianti landscapes as it journeys through woods, vineyards, and olive groves. Make a stop at the stunning monastery of Badia a Coltibuono. Monks took over this monastery in the 12th century and established a tradition of expert viticulture. It offers spectacular views over the Tuscan countryside from its lofty hillside look-out. On the way to the monastery, the road to Montegrossi passes the Castello di Montegrossi high on the cliffs above the roadside. Wander through the lovely little hamlet of Montegrossi and take the forest tracks skirting the hillside.
Stop at the Riecine Winery where a wine tour and tasting has been arranged. At this winery, there have been generations of winemakers since Etruscan times and their objective is to create the very best wines from Sangiovese, the indigenous grape of our Chianti Classico region.
After the tasting the walk heads back into the Valley of Gaiole to return to where the walk begins at the Church of San Sigismondo.
Ascent/Descent: 330m/328m
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Overnight Gaiole in Chianti
![]()
Accommodation
A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.
This exquisite 5* hotel is set in an ancient monastery from the 10th century. The large bedrooms have traditional Tuscan décor and panoramic views over the valley or the courtyard, and they have WiFi access and air conditioning. The outdoor pool has a waterfall and a sun terrace to sunbathe and relax on. It’s Il Pievano 1* Michelin restaurant is situated in the castle’s historic hall and offers a large wine list from the wine cellar. Candlelit dinners are also served out on the courtyard if preferred. Wine can be purchased from their shop to take home as a souvenir. There’s also a gym, tennis courts, table tennis, billiards room, heated indoor pool, sauna, tepidarium, Turkish bath, emotional showers, and spa treatments available (additional charges apply and advance booking is recommended).
Two-thirds of Chianti’s 70,000 hectares are still covered in oak woods where wild boar, hares, deer, and pheasants still reside, which there’s the possibility to spot en route today. The route follows tracks, quiet roads, and paths to wander amongst the famous vineyards of Castello di Meleto. Before crossing the rolling hills, pass villas, and through olive groves.
The destination of Hotel Le Fontanelle can be seen up on a ridge. It is a restored 13th-century mansion and in a very special locale with views all around.
We suggest departing from Gaiole-in Chianti early so that there’s time to make the most of the stay at this idyllic hotel, with its outdoor and indoor swimming pools, botanic garden, sauna, whirlpool, and steam bath. This evening dinner is included at the hotel.
Ascent/Descent: 498m/500m
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Overnight Hotel le Fontanelle
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Accommodation
A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.
This very beautiful estate is set in the middle of the gorgeous Chianti countryside, on a hill, giving fantastic views. It is a 13th century house that has been lovingly restored and captures the essence of Tuscany. Bedrooms are decorated in a traditional Tuscan style and have WiFi access and air conditioning. Relax in the spa which has an indoor swimming pool, sauna, Turkish bath, jacuzzi, sensorial shower, and massage rooms (additional charges apply for treatments and advance booking is recommended). Other on-site activities include a yoga studio, golf driving range, and tennis courts. The restaurant serves cuisine with artistic flair and refined taste. On our ‘Chianti In Style’ trip dinner on both nights is included.
Today is free to relax at this outstanding hotel. Perhaps use the opportunity to book a spa treatment, play a spot of tennis or practice on the golf pitch and putt. The hotel also offers guided tours of Firenze or San Gimignano, cooking classes, or horse riding excursions, so check out their website to book any of these options. Alternatively, this is an ideal spot to sit by the pool with a glass of wine and a good book.
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Overnight Hotel le Fontanelle
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Accommodation
A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.
This very beautiful estate is set in the middle of the gorgeous Chianti countryside, on a hill, giving fantastic views. It is a 13th century house that has been lovingly restored and captures the essence of Tuscany. Bedrooms are decorated in a traditional Tuscan style and have WiFi access and air conditioning. Relax in the spa which has an indoor swimming pool, sauna, Turkish bath, jacuzzi, sensorial shower, and massage rooms (additional charges apply for treatments and advance booking is recommended). Other on-site activities include a yoga studio, golf driving range, and tennis courts. The restaurant serves cuisine with artistic flair and refined taste. On our ‘Chianti In Style’ trip dinner on both nights is included.
Leave the lovely Hotel Le Fontanelle on foot and make the most of the last day of walking through these pristine and timeless landscapes. The route approaching Siena goes past the Basilicata dell’ Osservanza from where there are fantastic views over this glorious medieval city.
Siena is famous for the Piazza del Campo which is at the very core of the city and shaped like a scallop-shell. It is also the setting for the famous Palio horse race that takes place each summer. We recommend starting the walk early today to give plenty of time to explore this iconic city. If time allows, why not add an extra night here to fully enjoy the many attractions here.
Ascent/Descent: 397m/417m
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Overnight Siena
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Accommodation
A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.
Located within Palazzo Gori Pannilini, which was constructed around 1501, in the historic centre of Siena. This delightful aristocratic palace is the perfect embodiment of the finest Renaissance architecture. There are stunning and captivating frescoes and rich decorations that have been brought to light thanks to the various restoration projects carried out over the years. Bedrooms are individually decorated and have enchanting interiors using high quality fabrics and antique furnishings, and they have WiFi access and air conditioning. The large windows frame some of the best views that medieval Siena has to offer. The hotel also has a restaurant, wine cellar, and bar.
Right in the heart of Siena, this exceptional and elegant period residence offers a special stay and a very warm welcome. The light and airy rooms have frescoed ceilings, marble bathrooms, WiFi access, air conditioning, and some have private terraces. The building also features a large terrace overlooking the Church of San Domenico and the fortress. This is where breakfast is served and it’s possible to have an aperitif and watch the sunset over the city.
Reception is at your disposal every day from 7:30 am until 8:00 pm
Siena is easily accessible by train from Pisa, Florence and Rome.
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