Canvas Trip Board

Tuscany, Italy

Tuscany blends Renaissance cities, rolling hills, vineyards, medieval towns and beautiful countryside. This 6-day itinerary combines the highlights of Florence and Siena with scenic drives through Chianti and Val d’Orcia, with time to enjoy local food, wine and the relaxed atmosphere of Tuscany.

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6-Day Tuscany Itinerary: Art, Medieval Towns, Wine & Countryside Escapes

Day 1 - Arrival in Florence

Arrive in Florence and make your way to your accommodation. Check-in and settle in before heading out to explore. Enjoy your first Tuscan lunch and start exploring Florence on foot. Visit Piazza del Duomo, see the Cathedral and Baptistery, then continue towards Piazza della Signoria and Palazzo Vecchio. In the evening, enjoy dinner at a local trattoria.

Day 2 - Florence & Piazzale Michelangelo

Breakfast, visit the Uffizi Gallery or discover more of the historic centre, then cross the Arno to explore the Oltrarno neighbourhood and its artisan shops. Stop for lunch before continuing towards the Rose Garden and Piazzale Michelangelo. Enjoy the views over Florence around sunset, then return to the centre for a relaxed Tuscan dinner.

Day 3 - Florence, Chianti & Siena

Breakfast, check out of your Florence accommodation and drive into the Chianti countryside. Enjoy lunch at a traditional restaurant or winery, with the opportunity to taste local wine and Tuscan specialities. Continue towards Siena and check in to your accommodation before exploring Piazza del Campo and the surrounding historic streets.

Day 4 - Val d'Orcia

Breakfast, leave Siena and drive south towards the beautiful Val d'Orcia, stopping in Montalcino for lunch and, if you wish, a Brunello wine tasting. Continue to San Quirico d'Orcia and Bagno Vignoni before checking in to your countryside accommodation. Spend the evening relaxing and enjoy dinner at your accommodation or a nearby traditional restaurant.

Day 5 - Pienza & Montepulciano

Breakfast, visit Pienza, a charming Renaissance town with beautiful views across the Val d'Orcia. Explore the historic streets and stop for lunch. In the afternoon, continue to Montepulciano to explore Piazza Grande, the historic centre and its traditional wine cellars. Return to your countryside accommodation for a relaxed evening and a final Tuscan dinner

Day 6- Florence & Departure

Breakfast, enjoy one final morning in the Tuscan countryside before checking out. Depending on your departure time, make a final stop in a nearby village or enjoy a leisurely lunch on the way back to Florence. Return your rental car in Florence and continue with your onward journey.