About this trip
Eight days through southern Tuscany, built around the region's food and wine as much as its scenery. You're based in one of Italy's most photographed landscapes — rolling hills, cypress-lined roads and stone-built hilltop towns — with a small group and a guide throughout.
Expect a mix of city time in Siena, wine country in Chianti, and a run of hilltop towns including Montalcino, Pienza and San Gimignano, each with its own local specialities to taste along the way.
Meals are a big part of this one. There's a visit to an agriturismo for a proper farm-to-table meal, plus wine tastings ranging from Chianti to Brunello di Montalcino.
What you'll do
- Explore the historic centre of Siena
- Tour vineyards and olive groves in Chianti
- Taste Brunello and other local wines around Montalcino
- Wander the hilltop towns of Pienza and San Gimignano
- Eat a farm-to-table meal at a working agriturignano
- Drive through the Val d'Orcia's rolling hills and vineyards
- Easy-paced sightseeing rather than an active trip
- Private rooms throughout
- Strong focus on food and wine, so it suits travellers who want to eat and drink their way through the region
Worth it if you want stellar guides, wine and food experiences, and genuine hilltop beauty. Think twice if you need modern hotel comfort—rooms are in centuries-old buildings.
- Guides Esther and AJ consistently went beyond—nothing too much trouble, genuinely made the trip work.
- Pasta-making class with an enthusiastic teacher and farm visits with talks left people feeling inspired and genuinely connected.
- Hotel rooms are comfortable but in very old renovated buildings—expect period charm over modern amenities.
- Eight days gives decent free time in towns like Montalcino and San Gimignano, though some wanted more exploration hours.
Distilled from real traveller reviews on TourRadar — we don't edit out the bad bits.
The same-vibe trips, side by side — price, value per day, and how each is moving. Only we can lay two operators' trips out honestly.
Sorted by fit — never by who paid. Price moves and availability come from our own daily tracking.
Departing in Sep is cheapest — from £2,145, about 12% below the priciest month (May).
Getting there
Opens Trip.com, pre-filled — one-way so you can book your return whenever. Prices & booking shown there.
Where to stay
A night before your tour in Pisa · 5 Sept – 6 Sept
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