Tour Details
Tuscany is often imagined through its iconic landscapes but it is in the smaller villages and lesser-known corners that the true character of the region reveals itself. This tour is designed to take you beyond the surface, combining well-known highlights with places and experiences that are often missed.
Throughout the week, you’ll move through a series of Tuscan towns that each offer something distinct. From the medieval towers of San Gimignano to the historic streets of Siena and the carefully designed Renaissance town of Pienza, the journey provides a layered understanding of the region’s history and development.
Food is central to the experience, reflecting Tuscany’s deep connection to the land. From meals prepared with ingredients grown on-site, to visits with producers, you’ll see how simple, local produce is transformed into the region’s cuisine. A hands-on cooking experience further brings this to life, offering insight into traditional techniques and seasonal ingredients.
This is a tour that balances structure with freedom — guided visits alongside time to explore independently. Ideal for travellers who want to experience Tuscany not just as a destination, but as a way of life.
Tour Type: Small Group Tour (maximum of 14 guests)
Duration: 5 Days
Cost:
- Price: €2,600 or $4,399 AUD*
- Prices listed are based on twin share
- Single supplement: €300 or $599 AUD*
2027 Departures:
- 24 – 28 May
- 13 – 17 September
- 26 – 30 September
*Pricing and Currency Disclaimer:
All prices are listed in Euros (EUR). For customers paying in Australian Dollars (AUD), the final amount due will be subject to the currency conversion rate applicable at the time of final payment. Please note that exchange rates may vary, and additional fees may apply depending on your payment provider or financial institution.
Prices are set on Euros and this is the current AUD based on the exchange rate at time of publication.
Tour includes:
- A tour manager for the duration of the trip
- Accommodation in two 4-star hotels (Colle di Val d’Elsa and Pienza)
- All transport during the tour (private air-conditioned minibus with driver)
- All entry fees and guided visits as per itinerary
- Meals as listed: breakfast daily, plus a main meal each day (including wine)
Accommodation:
This tour is based across two Tuscan towns, allowing you to experience local life beyond daytime visits.
Your first two nights are in Colle di Val d’Elsa, staying at Palazzo San Lorenzo, located in the historic centre. The hotel combines central access with amenities including a garden, pool and spa.
The remaining nights are in Pienza, a beautifully preserved Renaissance town known for its pecorino cheese and relaxed atmosphere. Here we stay at Hotel Corsignano, within easy walking distance of the town centre.
Both hotels are 4-star.
Tour highlights:
- A journey through Tuscany’s most charming villages and countryside landscapes, combining well-known towns with lesser-known locations
- Visit iconic destinations including San Gimignano, Siena, Pienza, Volterra and Montepulciano
- Explore medieval and Renaissance towns, from hilltop villages to walled settlements like Monteriggioni
- Experience Tuscan cuisine through long lunches, a hands-on cooking class, and visits to local producers
- Unique experiences including an Etruscan tomb, Roman thermal baths at Bagno Vignoni, and a medieval abbey
- Stay in two Tuscan towns, allowing time to enjoy the atmosphere and local life in the evenings
- A relaxed pace with a balance of guided visits and free time to explore independently
- Small group touring, maximum of 14 guests
Physical Requirements:
This tour is not strenuous but involves regular walking at each location.
Participants should be comfortable being on their feet for extended periods, with guided visits lasting up to 2–2.5 hours.
Terrain includes cobblestones, steps, inclines and uneven surfaces.
An active lifestyle and general mobility are recommended.
Tour Notes:
This tour is based around walking at each destination, with short walks (10–15 minutes) often required from drop-off points due to traffic restrictions.
Daily schedule:
Most days begin between 8:30 – 9:00am and finish between 5:00 – 6:30pm.
Accommodation may vary, with some rooms requiring stairs and luggage handling.
Weather conditions may include heat, and appropriate preparation is recommended.
Day 1 – Castellina in Chianti – Volterra
We meet in Florence and head into the Tuscan countryside, an area that defines the classic imagery of Italy — rolling hills, vineyards and hilltop towns.
Our first stop is Castellina in Chianti, centred around a small piazza near a 15th-century castle. Here we take time to enjoy the village atmosphere, perhaps with a coffee or gelato.
Nearby, we visit the Etruscan Tomb of Montecalvario, dating back to the 6th century BC. This burial site, with its underground chambers, provides insight into one of the earliest civilisations in Tuscany, long before Roman influence.
We continue to a countryside restaurant for lunch, introducing you to Tuscan cuisine — simple, seasonal dishes closely tied to the surrounding land.
In the afternoon we visit Volterra, a classic hill town with both Etruscan and Roman heritage. After exploring together, you have free time to wander the cobbled streets, visit artisan workshops specialising in alabaster, or relax in the piazza.
We then continue to our accommodation in Colle di Val d’Elsa, where the medieval town centre sits just outside our hotel.
Meals: Lunch
Day 2 – San Gimignano – Tuscan Cooking
This morning we travel to San Gimignano, known for its medieval towers that dominate the skyline. Built by rival noble families, these towers remain one of the most distinctive features of the town.
We explore the town together, including some lesser-known areas, before giving you time to experience it at your own pace — from artisan workshops to gelaterias and panoramic viewpoints.
We then head to a countryside villa for a hands-on cooking experience. Here, under the guidance of a local chef, we learn the fundamentals of Tuscan cuisine — from ingredient selection to preparation techniques.
We explore the property, harvest seasonal produce, and prepare a meal together before sitting down to enjoy it.
Meals: Breakfast, Lunch
Day 3 – Siena – Monte Oliveto Maggiore – Pienza
We begin in Siena, exploring the city with a guided walk through its historic centre. You’ll learn about the city’s districts and their role in the Palio horse race, as well as visit the cathedral and Piazza del Campo.
After time to explore independently — perhaps enjoying local biscuits such as ricciarelli or cantucci in a historic café — we continue to the abbey of Monte Oliveto Maggiore.
This medieval monastery functioned as a self-sufficient community and remains active today. We explore its structures and learn about monastic life, including the production of goods such as wine.
In the afternoon we arrive in Pienza, a Renaissance town redesigned in the 15th century under papal direction. Today it offers a combination of architectural harmony, local food shops, and a relaxed atmosphere.
Meals: Breakfast
Day 4 – Bagno Vignoni – Flour Mill – Montepulciano
We begin at Bagno Vignoni, where thermal waters have been used since Roman times. The central pool and surrounding buildings create a unique setting that reflects its long history.
Next, we visit a rural flour mill, where traditional methods are still used to process locally grown wheat. After seeing the milling process, we enjoy a lunch featuring pasta made from the flour produced on-site, along with other estate-grown produce.
We then travel to Montepulciano, a town known for its wine production, particularly Vino Nobile di Montepulciano. We visit a winery and historic cellars, tasting a selection of wines and learning about the region’s winemaking traditions.
Meals: Breakfast, Lunch
Day 5 – Monteriggioni – Return to Florence
Our final stop is Monteriggioni, a small village still fully enclosed within its original medieval walls.
We spend time exploring the village, whether walking along the walls for panoramic views or relaxing in the central piazza.
Lunch is in a restaurant located within a 12th-century monastery complex, once used to house pilgrims travelling to Rome. The setting reflects centuries of history and offers a fitting final experience.
After lunch, we return to Florence, where the tour concludes in the afternoon.
Meals: Breakfast, Lunch
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