Chianti Hills Tour- 9 Days
Castellina in Chianti (2 nights), Ponzara in Chianti (2 nights), San Gamignano (2 nights), Volterra (2 nights)
This is a sample itinerary which is completely customizable, ask us how.
Highlights of the trip
- Village hop all over Chianti: Castellina, Ponzara, Montefioralle, Greve, Gaiola
- Visit medieval fortress villages: Siena, San Gamignano, Monteriggioni
- Same Chianti Classico at the source paired with local dishes
- Relax your mind and body in the thermal spa
- Ride around the hills of Chianti
Daily Itinerary
Day 1: Castellina in Chianti
Welcome to Castellina
Settle into your accommodation in Castellina in Chianti, a medieval town not to be missed in the Chianti area. There you can visit the enchanting church of San Salvatore and the Rocca, now home to the Archaeological Museum of Chianti Senese. Marvel at the breathtaking panorama from the terrace or year round. The main square comes alive during summer with an outdoor cinema.
Overnight: Castellina in Chianti
Day 2: Radda in Chianti and Castello di Albola
Castles and cellars in Chianti
Discover Radda in Chianti by bike before heading up to the Castello di Albola to visit its cellars followed by wine tasting and light lunch. We will take you up to the castle, looping around the gentle curves among rows of vines along the way. This is Tuscany.
Overnight: Castellina in Chianti
Day 3: Excursion to Siena
Stroll around Siena
Located near the Chianti region, Siena is a wonder in its own right. Step back in time into this UNESCO World Heritage town which also offers an insight into how many traditions have carried in into a modern Tuscany. Explored only by foot, our tour guide will make you see all the sites, learning about the history and traditions and taste the best food paired wine.
Later on our driver will take you to Panzano in Chianti for a guided tour through the streets of the village.
Overnight: Panzano in Chianti
Day 4: Day trip to Greve in Chianti
Discover more Chianti villages
Head back to Chianti for a day of discovering villages and wineries. Start with Greve in Chianti: here we stroll around Piazza Matteotti and peruse thd boutique shops topped off with a traditional lunch paired with wine.
Overnight: Panzano in Chianti
Day 5: Monsummano + Spa Grotta Giusti
Relax and recharge with a spa day in a cave
Enjoy a day trip to the Grotta Giusti in Monsummano – a unique, regenerating experience for both body and mind in the natural setting of the Pistoia province’s green hills. The Grotto is within the park of the 19th century villa once belonging to the poet Giuseppe Giusti’s family, embodying the “poetry of nature”. Today, it is a resort and wellness center with the highlight being the spa in a cave.
Day 6: Montefioralle in Chianti
Wine tasting in a characteristic village
Today after breakfast our driver will take you up to Montefioralle, one of the most characteristic villages of Chianti lined with narrow streets to get lost in and a fascinating history to surround yourself with. Stop for lunch in a historic restaurant serving up local dishes paired with wine before a second Chianti Classico tasting session at the Castello di Querceto.
Overnight: San Gimignano
Day 6: San Gimignano
An action packed day in San Gimignano
Visit the medieval town of San Gimignano, on par with Siena and another must-see for history, architecture and scenery. Wear something comfortable in case you would like to explore on horse back before wine tasting and a traditional lunch.
Overnight: San Gamignano
Day 7: Gaiole in Chianti, Vertine, Castello di Brolio and Badia a Coltibuono
Village hopping in Chianti
Our driver will ensure you leave no stone unturned with a leisurely day of Chianti village hopping, starting in Gaiole in Chianti.
After visiting Gaiole we make a stop at the Pieve di Santa Maria a Spaltenna, which dates back to the year 1000, before continuing in the direction of Vertine, a fraction of Gaiole.
One last stop before lunch. Castello di Brolio, whose history surrounds the Chianti Classico. Besides wine and its legendary aura, Brolio Castle boasts an amazing view of Siena in the distance beyond vineyards as far as the eye can see.
Overnight: San Gimignano
Day 8: Volterra
Volterra: an unspoiled Tuscan town
This walled town has deep roots in Etruscan history, still preserved to this day.
Let our local tour guide talk you through the historic importance of the sites and local traditions such as:
- Palazzo dei Priori, whose bell tower offers impressive views
- Volterra Cathedral to see the marbled entrance and unique ceiling
- Roman Theater, an archaeological site of ancient ruins
- Artisanal shops showing off the cities famous alabaster production.
Overnight: Volterra
Day 9: Excursion to Monteriggioni
Mighty Monteriggioni
Your tour ends with an unforgettable visit to Monteriggioni, a perfectly preserved quintessential Medieval fortified village that started its life as a castle, perfectly rounded to suit the hill on which it has stood since the beginning of 1200. Today its mighty towers are still visible for miles. Not as well known as Siena by foreigners, but excuding the same charm, you could say it’s one of the better kept secrets to end your trip on. It would be remiss not to stop for lunch before heading back for your last night in Volterra.
Overnight: Volterra
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