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Authentic Tuscany – 12 Days

Perfect for travelers who want to experience Tuscany beyond the cities — staying in the countryside at a relaxed pace. The focus is on Val d’Orcia and its surrounding villages, with just enough cultural highlights to give context without rushing.

Places Visited

Florence, Siena, Val d’Orcia (Pienza, Montalcino, San Quirico d’Orcia, Bagno Vignoni), Chianti

Duration

12 Days (fully customisable)

Activities

Guided city walks, countryside drives, winery visits and tastings, thermal bathing, village exploration, optional truffle hunting and cooking experiences

Perfect For

Travellers seeking an authentic Tuscan experience focused on countryside, food & wine, culture, and a relaxed pace

assistantTrip Details
location_onLocations

Authentic Tuscany – 12 Days

Perfect for travelers who want to experience Tuscany beyond the cities — staying in the
countryside at a relaxed pace. The focus is on Val d’Orcia and its surrounding villages, with
just enough cultural highlights to give context without rushing.

Daily Itinerary

Day 1 – Arrive in Florence

Cathedral at dusk Florence Tuscany 2

Arrive in Florence and transfer privately to your hotel. After check-in, enjoy a short orientation
walk to familiarise yourself with the historic centre. This evening, sit down to a relaxed
welcome dinner at a local restaurant, a simple introduction to Tuscan cuisine and the pace of
the journey ahead.

Overnight: Florence

Day 2 – Florence at Leisure

Cathedral view Pizza Florence Tuscany 1

After breakfast, explore Florence with a local guide on a walking tour that focuses on
everyday life as well as key historical sites. Visit quieter neighbourhoods, artisan areas and
local markets that give insight into how the city functions beyond its major landmarks. The
afternoon is free to continue exploring independently or relax at your own pace.

Overnight: Florence

Day 3 – Florence to Siena via the Countryside

Depart Florence and travel south through the Tuscan countryside. Along the way, stop at a
countryside estate or winery for a casual visit and tasting. Continue on to Siena, where a
guided walk introduces the city’s medieval layout, main squares and contrasting
neighbourhoods. Evening at leisure.

Overnight: Siena or nearby countryside

Day 4 – Siena and Surroundings

Experience the Thrilling Palio di Siena in Tuscany Spend the morning exploring Siena further, either independently or with an optional in-depth
guided tour focusing on the Palio traditions and local history. The afternoon is free, with the
option to enjoy a meal or short excursion into the surrounding countryside.

Overnight: Siena or nearby countryside

Day 5 – Siena to Val d’Orcia

Travel south from Siena into Val d’Orcia, where the landscape opens into rolling farmland and
vineyards. Stop in San Quirico d’Orcia for time to explore the village and enjoy lunch.
Continue to your countryside accommodation and spend the evening at leisure.