ItalyCities and culture · Nature and scenery · Slow travel
Florence and Tuscany · 5 unhurried days
Explore Florence’s art and craft neighbourhoods, then Siena, Pienza and Montepulciano’s old towns and countryside. Give the Val d’Orcia two days, with time to stop for cypress trees, stone houses and evening light.
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Places along the way
View the route on a map-
Florence
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Siena
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Pienza
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Montepulciano
Pace, season and who it suits
Pace City walks and countryside transport · Fewer hotel changes
Season Spring, early summer and autumn; fields change with the farming seasons
Who it suits Families and friends drawn to hill towns, photography and local food
Time for both art and countryside
Two days in the Val d’Orcia
Flexible stops for light and weather
01 Day 1
Florence
From the Duomo to the Arno
Spend the afternoon around the historic squares, Ponte Vecchio and the river. Save a substantial museum visit for tomorrow.
02 Day 2
Florence
A museum and a neighbourhood
Book one art museum to suit your interests, then explore the workshops and cafés of Oltrarno. Offer a lighter walking option for companions.
03 Day 3
Siena
Towers and the fan-shaped square
Travel to Siena in the morning and give its old town the main part of the day. Add an extra day if San Gimignano is also a priority.
04 Day 4
Val d’Orcia
Pienza and countryside light
Focus on Pienza and one countryside viewpoint. Stay within the area, enjoying the hills from public routes and respecting fields and private access.
05 Day 5
Montepulciano
A final hill town and a relaxed return
Spend the morning in Montepulciano. Any winery visit needs a booking and appropriate driving arrangements; leave the afternoon flexible for the onward journey.
DATES, COMPANIONS AND STOPS
Where would you like to spend more time?
Bring this itinerary and tell us your dates, travel companions and the places you most want to keep.
Enquire about this itinerary’s arrangementsBefore you travel3
- Countryside transport
- Arrange countryside transport in advance; rural services do not run like city transport.
- Where to base yourself
- Split the stay between Florence and Siena or the valley, checking parking and luggage access before entering old towns.
- Photography and weather
- Adjust viewpoints to the weather instead of treating famous photo spots as a checklist.
Itinerary and preparation
The itinerary can adapt to your dates, companions and interests. Bookings, transport and services are confirmed for the actual plan.
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