Tuscany by car in 7 days

Begin with a walk beside the Arno, following the river towards Ponte Vecchio and Oltrarno. The bridge’s shops and the streets on the far bank introduce a Florence that is enjoyable between its great collections as well as inside them. Settle into your accommodation, then let the length of the evening decide how far to wander. For dinner, look for ribollita, the bread-and-vegetable soup associated with Tuscan home cooking, or choose another simple trattoria meal. The river gives the first hours a gentle direction: cross a bridge, look back at the city and continue towards supper. If arrival is late, dinner near the hotel makes a pleasant beginning on its own. The car joins the route on day three, leaving these first two nights for walking and a full day of Florentine art.

• Arno and Ponte Vecchio
• Florentine dinner
• Oltrarno streets and trattorias

Overnight: Florence

Give the morning to the Uffizi or the cathedral complex, choosing the visit that most interests you. At the Uffizi, Renaissance paintings including Botticelli sit alongside ancient sculpture from the Medici collection. Spend time with a few works, enjoying the change between paintings and statues as you move through the gallery. A cathedral-focused day offers a different view of Florence through the monuments and climb you choose. Afterwards, have lunch and return to the Arno or continue into Oltrarno. Its streets make an easy setting for the afternoon, especially after a morning indoors. The two-night stay gives you an arrival evening and this full day: a main collection, a meal and a walk across the river make a satisfying introduction to the city before tomorrow’s drive.

• One main art reservation
• Renaissance paintings or the cathedral complex
• Flexible Oltrarno walk

Overnight: Florence

Collect the car as you leave Florence and head south to Siena. This is the point where the journey changes from a city stay on foot to a road trip through Tuscany. After arriving and parking, settle into the accommodation and walk towards Piazza del Campo. Its shell shape gives the first evening a memorable centre, with streets leading away into medieval Siena. Enjoy the square as a place to spend time, then choose somewhere for dinner. Tomorrow gives the cathedral and the city’s civic history a full day, so this arrival can be devoted to finding your way through the lanes and enjoying the evening. Two nights make Siena a stay in its own right between Florence’s art and the Val d’Orcia countryside.

• Collect the car and drive south from Florence
• Siena’s medieval lanes
• First evening on the Campo

Overnight: Siena

Leave the car parked and begin at Siena’s cathedral complex. Around it, look for the ambitious expansion that came to a halt in the fourteenth century, a reminder of the city’s scale and aspirations. Continue through the lanes to the shell-shaped Campo and Palazzo Pubblico. Together, these places bring Siena’s late-medieval civic power and rivalry with Florence into the day’s walk. At lunch, try pici, the thick handmade pasta, then stop at a bakery for panforte or ricciarelli. Moving between a great monument, a public square and a local table makes a full day feel varied. Spend the afternoon with another part of the cathedral complex or return to the streets that caught your attention in the morning. With a second night in Siena, there is time for an evening meal before the journey south.

• Cathedral art and the unfinished expansion
• Campo and medieval civic Siena
• Pici and local sweets

Overnight: Siena

Pause in Buonconvento on the drive towards Montalcino. Walk along Via Soccini, taking in the surviving walls and Porta Senese: a small town with a clear identity of its own along the route. The sharecropping museum offers a way into the rural life behind Tuscany’s scenery, while a shorter visit can be a walk and coffee in the village. Continue to Montalcino and settle in for two nights. Its fortress and town lanes make an appealing first evening, with dinner within walking distance when you choose a town room. Brunello comes from Sangiovese grown around Montalcino, linking the wine closely to this part of the journey. Enjoy the atmosphere of the town as the countryside becomes the week’s main setting. Tomorrow’s outing to Pienza returns here for another evening.

• Buonconvento and Via Soccini
• Montalcino fortress area
• A first Montalcino evening and a local meal

Overnight: Montalcino

Make Pienza the day’s main outing. Pope Pius II transformed his birthplace in the fifteenth century, and Piazza Pio II, the cathedral and Palazzo Piccolomini show the Renaissance idea of an ordered town in a compact setting. Spend time in the square before walking towards the edge of the historic centre for the valley view. Pecorino gives the visit another local pleasure: taste some or buy a small piece from a shop. On the return towards Montalcino, leave time for a walk or a viewpoint with a proper stopping place. UNESCO recognises the Val d’Orcia as a cultivated landscape shaped by settlement, farming and artistic ideals. Looking across it after visiting Pienza helps connect the towns and fields as parts of the same story. A booked wine tasting can replace part of the outing if that is how you would most like to spend the afternoon.

• Pienza’s Renaissance square
• Pecorino and a valley view
• A walk or viewpoint in the cultivated valley

Overnight: Montalcino

Enjoy a final short walk in Montalcino when your departure leaves time, then drive to the agreed rental-return location. Returning to the Florence area makes the week a loop, bringing the countryside part of the trip back towards its starting city. Give the handover its own place in the day alongside refuelling and the onward journey. After six nights, there is a pleasing progression to look back on: Florence’s paintings and river, Siena’s cathedral and civic square, Buonconvento’s village streets and Pienza’s Renaissance plan above the valley. The two nights in Montalcino have allowed an outing into the Val d’Orcia with the comfort of returning to the same room. Collection on day three and return on day seven span five calendar days.

• A final walk near the fortress and town streets
• Drive to the agreed rental-return location
• Complete the six-night Tuscan loop

Base: Montalcino and Val d'Orcia