Tour · 7 nights · with Explore Worldwide
A Taste of Tuscany - Hilltop Towns and Vineyards
A small-group escorted tour with Explore Worldwide through southern Tuscany’s hilltop towns and vineyards, including Siena, Montalcino and San Gimignano, with a focus on food, wine and local produce.
- Duration
- 7 nights
- Departures
- 6 dates
- Choose a month below
- Countries
- Italy
- Operator
- Explore Worldwide
- From
- £2,395
- per person
Highlights
What makes this one worth it
Piazza del Campo and Duomo in Siena
Brunello di Montalcino wine tasting
Pecorino cheese tasting in Pienza
Medieval towers of San Gimignano
Organic farm visit near Volterra
About the trip
This week-long tour by Explore Worldwide takes a measured route through southern Tuscany’s medieval towns and gently rolling countryside. Starting in Pisa, a brief orientation stroll introduces the Campo dei Miracoli and its famously leaning tower. The journey then swings to Livorno’s vast Central Market, where locals still source their daily fish and vegetables, before heading into the hills of the Val d’Orcia to taste Brunello di Montalcino in a walled hilltop town.
After a farm walk and lunch at an organic cereal producer in Buonconvento, the tour moves on to Pienza for pecorino cheese tastings, then spends two nights in Siena. There’s a chance to admire the Duomo and the Piazza del Campo, where twice-yearly horse races fill the square. Later stops include Chianti’s Castello di Volpaia wine estate and the medieval towers of San Gimignano, with its view-studded main square.
The final days include a visit to a sheep farm near Volterra for cheese and lunch, followed by free time in the town itself. The holiday ends in San Gimignano with a cooking class and a farewell dinner on the farm, the pace balanced between guided highlights and moments to savour quietly.
- 1 Pisa
- 2 Siena
- 3 San Gimignano
- 4 Volterra
- 5 Montalcino
Itinerary
The route
Pisa
Siena
San Gimignano
Volterra
Montalcino
These are the places the trip visits, in order. Explore Worldwide publishes the day-by-day itinerary on its own site.
When to go
Departures and prices
Lowest price each month, per person.
Explore Worldwide confirms exact dates, availability and prices when you book.
Need to know
Before you book
- Price based on
- Per personThe operator confirms the exact basis when you book.
- Travelling alone
- Check with Explore Worldwide
- Flights
- Not included: you book your own to the start
- What’s included
- Check with Explore Worldwide
- Accessibility
- Check with Explore Worldwide
For full details of what’s included, check with Explore Worldwide. See the full details on their site
Questions people ask
- How long is A Taste of Tuscany - Hilltop Towns and Vineyards?
- A Taste of Tuscany - Hilltop Towns and Vineyards is a 7 nights tour holiday.
- Who operates A Taste of Tuscany - Hilltop Towns and Vineyards?
- A Taste of Tuscany - Hilltop Towns and Vineyards is operated by Explore Worldwide.
- How much does A Taste of Tuscany - Hilltop Towns and Vineyards cost?
- Prices for A Taste of Tuscany - Hilltop Towns and Vineyards start from £2,395, subject to availability.
The operator
Explore Worldwide
Small-group adventures, walking and wildlife
Small groups with local leaders, and a fondness for the places at the end of the road. Trips are graded so you know how active they are.
You book with Explore Worldwide directly. They confirm your place, take payment, and look after you from the moment you leave home; Atlas & Passage’s part ends when you click through.
New to Italy? Our Italy guide has the practical essentials: money, plugs, visas and when to go.
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