Tuscany itinerary: hill towns, wine roads and Val d'Orcia
Tuscany outside Florence is a driving trip, and the mistakes are predictable: too many hill towns in a day, and a fine for entering a town's restricted traffic zone. This prompt asks your todo.is agent to plan a calm Tuscany route from one or two countryside bases, with wineries, the famous cypress roads and parking for every town.
The prompt
- Plan a Tuscany itinerary for [NUMBER OF DAYS] days, [TRAVEL DATES], for [WHO IS TRAVELLING], with a rental car from [START CITY]. Use one or two agriturismo bases (suggest areas) and visit at most two towns a day. Include Siena, San Gimignano, a Chianti drive with two winery tastings, Val d'Orcia (Pienza, Montalcino, Montepulciano, Bagno Vignoni) and [EXTRA PLACES]. For every town, give the car park outside the ZTL so we avoid fines. Our interests: [INTERESTS]. Suggest a trattoria per day and the local dish to order. Send a PDF day by day with drive times and links, plus a short packing note for the season. Don't book anything.
What to change
- [NUMBER OF DAYS]: E.g. "6". Five to seven days lets you settle into two bases.
- [TRAVEL DATES]: E.g. "6 to 12 May". May, June, September and October are best; harvest is September to October.
- [WHO IS TRAVELLING]: E.g. "couple", "family with two teens", "four friends who like wine".
- [START CITY]: E.g. "Florence", "Pisa airport", "Rome".
- [EXTRA PLACES]: E.g. "Lucca and Pisa", "Volterra", "Cortona", "Saturnia hot springs".
- [INTERESTS]: E.g. "wine, food, photography, art, easy walks".
Example result
- Tuscany in 6 days, couple, rental car from Florence
- Wine, food, views · mid-May
- Base 1: Chianti, near Castellina or Radda (3 nights)
- Day 1: Into Chianti
- • Pick up the car outside Florence's centre (driving into the ZTL brings fines).
- • Drive the SR222 Chiantigiana through Greve in Chianti (about 45 min). Walk the triangular piazza.
- • Late afternoon: first tasting of Chianti Classico at a family estate.
- Day 2: San Gimignano and Volterra
- • Morning: San Gimignano's towers before the coach groups. Try the Vernaccia white.
- • Afternoon: Volterra, an Etruscan town with alabaster workshops and wide views.
- • Dinner back at the agriturismo.
- Day 3: Siena
- • Morning: Piazza del Campo and the Duomo with its striped columns and marble floor.
- • Afternoon: the Torre del Mangia climb if you like stairs, then pici pasta in a side street.
- • Park at a car park outside the walls and walk or take the escalators up.
- Base 2: Val d'Orcia, near Pienza or San Quirico (3 nights)
- Day 4: Montalcino and Sant'Antimo
- • Drive south through the Crete Senesi clay hills (about 1.5 hours).
- • Afternoon: Brunello tasting in Montalcino, then the Romanesque Abbey of Sant'Antimo.
- Day 5: Pienza and Montepulciano
- • Morning: Pienza, the Renaissance 'ideal town'. Buy pecorino.
- • Afternoon: Montepulciano's main street uphill, then a Vino Nobile cellar.
- • Sunset: the cypress viewpoints near San Quirico d'Orcia and the Cappella di Vitaleta.
- Day 6: Bagno Vignoni and back
- • Morning: the thermal pool square in Bagno Vignoni (look, don't swim), with a spa nearby.
- • Drive to Florence or Rome (about 2 hours).
- Good to know
- • Almost every town has a ZTL. Park in signposted car parks outside the walls.
- • Tastings usually need booking. Don't drink and drive; take one designated driver or a guided tour.
- • All car parks, wineries and restaurant links are in the PDF.
How to do it with todo.is
- Copy the prompt and fill in your days, dates, group, start city and extras.
- Paste it on the Today screen in todo.is, or send it to your agent on WhatsApp or Telegram.
- Your agent plans the bases, the drives and ZTL-safe parking, and sends you a PDF.
- Reply with changes like "add Lucca by bike" or "one base only". You book the car, rooms and tastings.
Tips for a better result
- Stay in two bases rather than changing hotels every night. Chianti and Val d'Orcia cover most highlights.
- Respect the ZTL signs. Cameras fine you automatically, sometimes months later through your rental company.
- Plan one big town and one small village a day. The best Tuscany moments happen between the sights.
- Ask your agent to book nothing but to list tasting times, so you can email the wineries yourself.
Tuscany itinerary: FAQ
- How many days do you need in Tuscany? Five to seven days lets you see Siena, San Gimignano, Chianti and Val d'Orcia without rushing. With three days, pick Chianti and Siena.
- Do you need a car in Tuscany? For the countryside, yes. Siena, Lucca and Pisa are easy by train or bus, but wineries and Val d'Orcia need a car or a guided tour.
- What is a ZTL in Tuscany? A Zona a Traffico Limitato is a restricted traffic zone in a historic centre. Driving in without a permit triggers a camera fine, so park outside.
- When is the best time to visit Tuscany? Late April to June and September to October. The grape harvest is in September and October, and summer is hot and busy.
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