A week in Tuscany works best with two bases: four nights in Florence, then three in Siena. From Florence you cover the city, Fiesole, Chianti Classico and San Gimignano. From Siena, Montalcino is 41 km away instead of about 120, which takes roughly two hours of driving off the Val d’Orcia day. Plan one area per day, with two stops at most.
| Day | Sleep in | Where the day goes | Distance from base | The day we run |
|---|---|---|---|---|
| 1 | Florence | Historic centre, the Arno in the evening | On foot | Florence Boat & Wine |
| 2 | Florence | Fiesole hills, then one museum | 9 km on foot | Florence Hike & Wine |
| 3 | Florence | Chianti Classico | 30–60 km | Chianti Classico Wine Hiking Tour or Wine Tour |
| 4 | Florence | San Gimignano and Certaldo Alto | 56 km | San Gimignano & Certaldo |
| 5 | Siena | Transfer, then Siena on foot | 75 km | Train or private driver |
| 6 | Siena | Montalcino, Pienza, Val d’Orcia | 41–56 km | Brunello di Montalcino Wine Tour |
| 7 | Siena | Crete Senesi, or nothing at all | Close to Siena | Truffle Hunting with Lunch |
What does a 7-day Tuscany itinerary look like?
Four days out of Florence, three out of Siena, and one hotel change on day 5. The rules behind our 3-day itinerary from Florence hold the week together:
- One area per day, two destinations at most. A third stop turns the day into a transfer.
- One light day. Here it is day 5, the move to Siena. Three full days out in a row is comfortable; four in a row is tiring.
- Nobody drives after a tasting. Three of these days are built around wine, so a guide or a driver takes the wheel.
Still deciding between five, seven and ten days? Start with how many days you need in Tuscany.
Why split the week between Florence and Siena?
Montalcino is about 120 km from Florence and 41 km from Siena. That difference decides the shape of the week.
From Florence, our Val d’Orcia and Brunello days run ten hours door to door, with roughly two hours in the van each way. From Siena, Montalcino is about 50 minutes away and Pienza about an hour and ten. You are back at the hotel well before dinner.
Florence still earns the first four nights. Chianti Classico starts about 20 km south of the city, San Gimignano is 56 km away, and the first days of a trip, with jet lag, are the wrong time for long drives. Distances for every other destination are in our guide to the best day trips from Florence.
One practical point. Siena’s historic centre is a restricted traffic zone, like Florence’s. If your hotel is inside the walls, our private tours from Siena start from a meeting point just outside, which we confirm when you book.
Day 1: What should you do on the day you arrive in Florence?
Stay on foot. You will be tired, the centre is a camera-enforced ZTL where a rental car collects fines, and almost everything worth seeing on a first day is within walking distance of the Duomo.
In the early evening, the Florence Boat & Wine spends an hour on the Arno, under Ponte Vecchio and past the Uffizi, with a glass of organic prosecco. It is an easy way to stay awake until dinner.
Day 2: How do you fit the Fiesole hills and a museum into one day?
Walk in the morning, museum in the afternoon. Jet lag tends to wake people early, and the morning Florence Hike & Wine leaves at 8:30: 9 km and about 250 m of climbing into the hills of Fiesole, a glass of wine on a bench facing the Duomo, then lunch at an organic farm.
You are back in Florence by early afternoon. Pick one museum, the Uffizi or the Accademia, and book the entry time before you travel. Two big museums in one afternoon is the city version of three towns in a day.
Day 3: Should you spend your Chianti Classico day on foot, by van or in a kitchen?
Chianti Classico is the closest wine country to Florence. The estates we visit sit 30 to 60 km out, under an hour each way, and there are three good ways to spend the day there:
- On foot. The Chianti Classico Wine Hiking Tour walks about 8 km of vineyard trails between three small organic wineries, with lunch at a family-run estate. Nine hours, easy to moderate, for people happy to walk most of the day.
- By van. The Chianti Classico Wine Tour visits two organic estates in five hours, with lunch at one of them, and gives you back the late afternoon in Florence.
- In a kitchen. A home cooking class in Chianti Classico runs from 9:30 to 14:00. You cook four courses with the chef, then eat them with wine.
If you are torn between Chianti and Montalcino for your one big wine day, our Chianti vs Montalcino comparison puts them side by side. On this itinerary you get both.
Day 4: San Gimignano and Certaldo, or Pisa and Lucca?
San Gimignano is 56 km from Florence. We pair it with Certaldo Alto, in the same valley, and leave Siena for the second half of the week. Our San Gimignano & Certaldo day takes seven hours, with lunch and three wines at an organic winery overlooking the towers.
Timing matters more here than anywhere else in the week. San Gimignano fills up from mid-morning, so arrive before 9:30 or after 5 pm. The tour goes there first thing.
Prefer the Leaning Tower to medieval ones? Pisa is 80 km from Florence, about an hour by train with departures every half hour, and Lucca is on the same line. Both work without a car or a guide.
And if the coast matters more than any of this, swap in Cinque Terre and Pisa: eleven hours from Florence, three or four villages and the Leaning Tower. It is the longest day of the week, which is why it belongs here, the day before the light one.
Day 5: How do you move from Florence to Siena without losing the day?
Make it the light day. Siena is 75 km south of Florence, about an hour and twenty minutes by road or an hour and a half by train via Empoli.
With luggage, a private driver is simpler than the train: from your hotel in Florence to your hotel in Siena, or to the closest point outside the restricted zone.
Check in, then give Siena the rest of the day. Piazza del Campo needs an unhurried afternoon, and the evening is better still, once the day-trip coaches have gone.
Day 6: Why is Montalcino easier from Siena than from Florence?
It is 41 km from Siena, about 50 minutes by road, against roughly two hours from Florence. Pienza is about an hour and ten from Siena.
The Brunello di Montalcino Wine Tour starts from Siena as well as Florence. You get a guided tasting at a small organic winery in Montalcino, then lunch at a farm-to-table restaurant in the Val d’Orcia or at a second Brunello estate, and time to walk Pienza or Monticchiello.
If you would rather see the valley than its cellars, the Val d’Orcia day covers Pienza, Monticchiello and a farm lunch, with a winery only if you ask for one.
Plan it once. Two Val d’Orcia days in the same week, even from Siena, mostly add hours in the van.
Day 7: Truffles in the Crete Senesi, or a day off?
Keep the last day short. There are bags to pack and an airport transfer the next morning.
- Truffle hunting. Truffle Hunting with Lunch is half a day in the woods with a truffle hunter and a trained dog, then lunch built around what you find. From Siena we go to the Crete Senesi. The truffle changes with the month: white from October, black from November to March, summer truffles from mid-June.
- Gravel. Cyclists can ride the strade bianche and the Eroica roads on a guided gravel bike day that starts directly from Siena.
- Nothing at all. Coffee in the Campo and a slow walk to the Duomo make a perfectly good last day.
What should you leave out of a week in Tuscany?
- The Cinque Terre, unless it replaces day 4. With the Val d’Orcia already in the plan, a second very long day makes the week heavier than it looks on paper. Ten days fit both.
- Day trips to Rome or Venice. Each one costs a Tuscan day for a few rushed hours in a city that deserves several days.
- A third destination on any day. Chianti, Siena and San Gimignano in one day is a coach tour itinerary, and it shows.
- A rental car on wine days. Our guide to whether you need a car in Tuscany explains when self-drive makes sense and when it doesn’t.
- A third hotel. Every extra change costs half a day of packing and checking in.
Can you change this itinerary?
Every day of it. This is the order we would start from for a first visit built around wine, some walking and the classic towns. Hikers, cyclists and families usually end up with something quite different, and the season moves things too: our month-by-month guide to Tuscany shows what changes when.
Tell us your dates, who is travelling and what you care about. We send back a written day-by-day plan with a full quote, usually within 48 hours, and you can change anything before confirming. That is how our tailor-made Tuscany tours work. You can also browse every day trip that starts from Siena.
FAQ
Seven days is enough for Florence, Chianti Classico, San Gimignano, Siena and the Val d’Orcia, at a pace that still leaves one day light. It is too short to add the Cinque Terre without rushing. If the coast matters, plan ten days, or swap the San Gimignano day for the coast and accept a very long day.
Split the week between two bases: four nights in Florence, then three in Siena. Florence covers the city, Fiesole, Chianti Classico and San Gimignano. From Siena, Montalcino is 41 km away instead of about 120, so the Val d’Orcia day loses roughly two hours of driving. One hotel change is enough.
Three nights in Siena give you Piazza del Campo in the evening, after the day-trip coaches leave, and put Montalcino, Pienza and the Crete Senesi within about an hour. A day trip gives Siena a few hours between two drives. On trips of five days or less, the day trip from Florence is enough.
Only by giving up another day. The Cinque Terre are about 220 km from Florence, and a day there runs 11 to 12 hours, with or without hiking. In a week, swap it for the San Gimignano day and leave from Florence, never from Siena. With ten days, the coast fits without squeezing the rest.
Plan ten hours door to door. Montalcino is about 120 km from Florence, roughly two hours each way, and that is how long our Val d’Orcia and Brunello days from Florence take. Once in a week is fine; twice is too much. Sleeping in Siena cuts the drive to Montalcino to about 50 minutes.
Late April to early June, and mid-September to the end of October. Spring has long evenings and the best walking weather; autumn has the grape harvest, then new olive oil and white truffles in November. In July and August the countryside reaches 35 to 38°C, so every long day needs an early start.
Every day here can move or change. Tell us your dates, who is travelling and what matters most, whether that is wine, walking or one particular town, and we send back a written day-by-day plan with a full quote, usually within 48 hours. Most guests adjust it once or twice before confirming.
