Tuscany: 7-day Itinerary
Discover Tuscany on a 7-day itinerary through Renaissance cities, medieval hill towns, vineyard-covered countryside and the timeless landscapes of the Val d’Orcia.
Day 1.
Florence Airport → Florence
Travel: ± 30 minutes
Arrive at Florence Airport and make your way into the city. It is best to collect your rental car the following morning, as much of Florence’s historic centre is a restricted traffic zone.
Spend the afternoon exploring the magnificent Duomo, Piazza della Signoria and the medieval streets around Santa Croce.
In the evening, cross the Ponte Vecchio and head into Oltrarno, a lively neighbourhood filled with artisan workshops, intimate wine bars and traditional trattorias.
Stay: Florence
Day 2.
Florence → Greve in Chianti → Montefioralle → Siena
Driving: ± 1 hr 45 total
Collect your rental car and leave Florence behind for the rolling vineyards and olive groves of the Chianti region.
Stop in Greve in Chianti to explore its historic main square, browse local food shops and enjoy the relaxed atmosphere of this famous wine-producing area.
Continue to Montefioralle, a tiny fortified village with stone houses and narrow lanes, before taking the scenic road south towards Siena.
Spend the evening discovering Piazza del Campo and the atmospheric streets of Siena’s historic centre.
Stay: Siena
Day 3.
Siena → Monteriggioni → San Gimignano
Driving: ± 1 hr total
Begin the day with more time in Siena. Visit its striped marble cathedral, wander through the medieval contrade and enjoy the view from one of the city’s panoramic terraces.
Drive to Monteriggioni, a beautifully preserved walled village surrounded by vineyards and crowned by medieval towers.
Continue to San Gimignano, known for its distinctive skyline of stone towers. Explore the historic centre once the afternoon crowds begin to disappear and enjoy the quieter evening atmosphere.
Stay: San Gimignano or the surrounding countryside
Day 4.
San Gimignano → Volterra → Pienza
Driving: ± 3 hrs total
Leave San Gimignano for Volterra, an ancient hill town with Etruscan origins, impressive Roman ruins and a long tradition of alabaster craftsmanship.
After lunch, continue south through the Tuscan countryside towards the Val d’Orcia. The final stretch passes rolling hills, cypress-lined roads and isolated farmhouses.
Arrive in Pienza in time for an evening walk through its compact Renaissance centre and along the panoramic walkway overlooking the valley.
Stay: Pienza or the Val d’Orcia
Day 5.
Pienza → Bagno Vignoni → San Quirico d’Orcia → Montalcino
Driving: ± 1 hr 45 total
Start the day in Bagno Vignoni, a remarkable village built around a large thermal pool that has occupied its central square for centuries.
Continue to nearby San Quirico d’Orcia, where quiet medieval streets, hidden courtyards and the gardens of Horti Leonini make it well worth a stop.
Spend the afternoon in Montalcino, a hilltop town surrounded by the vineyards that produce Brunello di Montalcino. Visit the fortress, explore the historic centre or arrange a tasting at a nearby wine estate.
Return through the Val d’Orcia for a second night in the countryside.
Stay: Pienza or the Val d’Orcia
Day 6.
Pienza → Montepulciano → Cortona
Driving: ± 1 hr 15 total
Drive to Montepulciano, an elegant hill town filled with Renaissance palaces, historic wine cellars and sweeping views across the Val di Chiana.
Walk uphill along the Corso to Piazza Grande and sample the local Vino Nobile di Montepulciano before continuing east.
Spend the afternoon in Cortona, where steep medieval streets lead to small piazzas and viewpoints overlooking the valley and Lake Trasimeno.
Stay: Cortona
Day 7.
Cortona → Arezzo → Florence Airport
Driving: ± 2 hrs total
Leave Cortona and stop in Arezzo, a historic city that remains quieter than many of Tuscany’s better-known destinations.
Explore Piazza Grande, admire the medieval architecture and visit the Basilica of San Francesco, home to Piero della Francesca’s celebrated fresco cycle.
Enjoy a final Tuscan lunch before driving back to Florence Airport to return your rental car and complete the journey.