Photo by Intrepid on Unsplash
Five easy days by car: a day in Siena, a roofless abbey and a walled village, the hill towns of the Val d'Orcia, Montalcino with its abbey in the olive trees, then the pale clay hills and the castles of Chianti. Short drives, long lunches and open afternoons.
From average weather, 2021 to 2025: days that are warm but not hot, with few rainy days, score highest. Crowds and prices change through the year, so check them before you book.
A walking day in a hill city of brick and marble. A black and white cathedral, a shell-shaped square, a tall tower to climb and a green park on the old fortress as the day ends.
Italian breakfast: a coffee drunk standing at the counter and a filled croissant. Quick, cheap and the way locals start the day.
Local tip Order at the till first in busy places, then take the receipt to the bar.
A Gothic cathedral in black and white marble stripes, with a carved pulpit, a library of bright frescoes and a floor inlaid with pictures in stone. The inlaid floor is often covered, so check ahead.
Go when Morning, when the light comes through the doors and the lanes are quiet.
Local tip Look down as well as up. The floor is a picture book in stone, and it is often covered, so check ahead. Cover your shoulders and knees.
The shell-shaped brick square in the middle of Siena, sloping gently to the town hall. The Palio horse race is run around its edge twice each summer. Sit on the bricks and watch the square fill and empty.
Go when Midday, with a seat on the bricks.
Local tip Walk to the low end by the town hall and look back up the slope. In the Palio weeks the square is closed to everyone but the riders, so check ahead.
Pici are thick, hand-rolled spaghetti typical of the Siena area, served with a slow meat sauce or with garlic and tomato. Rustic and filling.
Local tip Ask for the pasta of the day, which is often made by hand.
The slender brick tower beside the town hall, from the 14th century. A climb of several hundred steps ends in a view over the roofs and out to the hills. Check ahead on opening, and go early in the heat.
Go when Early morning, before the heat and the queue.
Local tip The steps are narrow and steep, so take water and go slowly. Check ahead on opening and how many people are let up at once.
A 16th century fortress that the Medici built to hold the city, now a quiet park with walls to walk and a view back to the cathedral. A good place to be as the light turns gold.
Go when Early evening, around sunset (about 8:31 PM).
Local tip Walk the walls and look back at the cathedral dome. Locals bring a picnic here when the day cools.
Siena's two famous sweets: soft almond biscuits and a dense spiced fruit and nut cake. Buy a slice to share with a coffee or a glass of sweet wine.
Local tip Panforte keeps for weeks and travels well, so buy extra to take home.
A day out west. A roofless abbey in a field, a hermitage on the hill above it, a small village ringed by walls and, at the end, a hill town of tall stone towers.
A 13th century Cistercian abbey with no roof, so the grass is the floor and the sky is the ceiling. The stone arches stand in an open field. It is a quiet place, so early morning is best.
Go when Early morning, in soft light.
Local tip Walk inside the roofless nave on the grass and look up. It is best on a clear day, when the arches frame the sky.
A small round chapel on the hill above the abbey, said to hold the sword of Saint Galgano in a stone. A short walk up, with a calm view of the fields. Check ahead on opening.
Go when Midday, after the abbey.
Local tip It is a short, easy walk up. The chapel is round and plain, and the sword is under a glass case. Check ahead on opening.
A thick winter soup of beans, bread and black cabbage, reheated until it is almost a stew. Plain, warm and very Tuscan.
Local tip In summer ask for panzanella, a cold salad of bread, tomato and basil.
A small village inside a ring of 13th century walls and towers on a low hill. Dante compared its towers to giants. Walk the lanes in a few minutes and sit in the little square.
Go when Afternoon, then drive on.
Local tip You can walk the whole village in a few minutes. Climb the section of wall for the view, and sit in the small square.
A hill town of tall stone towers that rise above the roofs, a rich medieval merchants' skyline. Come late, when the day visitors leave, and walk the lanes and the main square.
Go when Late afternoon and early evening, when the day visitors go.
Local tip Park outside the walls and walk up. The best view of the towers is from the road coming in, so stop in a lay-by on the way.
Vernaccia is the white wine of San Gimignano, crisp and dry, good with a board of cured pork, salami and pecorino.
Local tip Share the driving or stay close to your room.
The postcard Tuscany. A chapel among cypresses, a small town planned as an ideal city, a walled village on a ridge and a big square on a hill at the end of the day.
A slice of unsalted Tuscan bread with new green olive oil, eaten with a coffee. Simple and good.
Local tip The oil is at its best in the weeks after the harvest in autumn.
A tiny chapel on a green knoll among cypress trees, one of the best-known views in Tuscany. Park at the roadside, walk up the track and look. The light is softest early.
Go when Early morning, in soft light and mist.
Local tip Park at the roadside and walk up the track. The chapel is small and usually closed, so the view is the point. Keep off the crops.
A small town rebuilt in the 15th century by Pope Pius II, who was born there, as an ideal Renaissance city. A square, a cathedral and a palace, and a view over the valley from the wall. The sheep cheese here is famous.
Go when Late morning, with lunch to follow.
Local tip Walk along the wall on the south side for the view of the valley. Look for the pecorino cheese in the shops and ask for a taste.
The sheep cheese of Pienza served young and soft or aged and sharp, with honey or fruit. A light lunch on its own or before pasta.
Local tip Ask for a mix of young and aged, and eat the young one first.
A small walled village on a hilltop east of Pienza, quiet and car-free inside the gate. Walk through the lanes and look over the Val d'Orcia.
Go when Afternoon, when the village is quiet.
Local tip Walk the lane inside the walls to the viewpoint. It is a real village where people live, so keep your voice down.
A long hill town on a ridge, with a stepped main street, wine cellars cut into the rock and a big square at the top. Climb slowly and stay for the evening light.
Go when Evening, as the stone turns gold (about 8:31 PM).
Local tip The main street climbs the whole way, so take it slowly. At the top, the square has a tower and a view across two valleys.
A rich ragù of wild boar, called cinghiale, a Tuscan favorite, served on wide ribbons of pasta or with polenta.
Local tip It is hearty, so order a half portion if you are not very hungry.
A day of wine hills and warm water. A fortress town above the vineyards, a Romanesque abbey in the olive trees, a castle on a rock and a square with a steaming pool at its heart.
A hill town with a 14th century fortress at the top and vineyards all around, known for its red wine. Walk up to the walls and look over the valley. Tastings are on offer, so share the driving.
Go when Morning, before the heat.
Local tip Walk up to the fortress and look over the vineyards. Wine tasting is part of the town, so share the driving or leave the car behind.
Toasted bread with chicken liver spread, tomato or olive paste, served as a starter to share. A small, savory way to start a long lunch.
Local tip Order a mixed plate and ask which toppings are made in house.
A Romanesque abbey of pale stone alone among olive trees, with a calm interior. Monks sometimes sing plainchant in the church. Check ahead for times and for what is open.
Go when Midday, when the stone is warm and the olive trees are bright.
Local tip Check ahead for times of the monks' singing, which draws a small crowd. Dress modestly for the church.
A small village below a castle on a rock, with the valley spread out below. Walk up to the keep and look over the whole of the Val d'Orcia.
Go when Afternoon, with the valley below.
Local tip The path up to the castle is short but steep. The best part is the view, so go up in good light.
A cone from a small gelateria. Choose seasonal flavors such as fig, ricotta or fior di latte.
Local tip Look for a shop that stores its gelato in covered tubs rather than piled up in bright mounds.
A village with a large pool of steaming spring water in the middle of its square, where people have come to take the waters since Roman times. You cannot swim in the square, but you can sit by it as the day ends.
Go when Evening, as the steam rises in the cool air.
Local tip The big pool in the square is for looking at, not swimming. Walk down the path behind the village to see where the warm water runs off the cliff.
Slices of grilled beef served rare on rocket with a little olive oil, rosemary and flakes of cheese. A light, simple dinner.
Local tip Share a plate, and add a side of beans or roast potatoes.
A last day of open country. A monastery in the cypress woods, the bare pale hills of the Crete Senesi, a castle at the heart of Chianti and a small hill town at the end of the road to Florence.
A large brick monastery in a wood of cypresses, with a cloister painted with scenes from the life of Saint Benedict. Quiet and shaded, and a good start to a long day. Check ahead on opening.
Go when Morning, when the cloister is quiet.
Local tip Look closely at the frescoes in the great cloister, which tell the life of Saint Benedict in lively scenes. Check ahead on opening.
Many farms near the abbey serve a simple lunch of homemade pasta, vegetables from the garden and local cheese.
Local tip Book ahead and ask what is picked that week.
The pale clay hills south of Siena, bare and rolling, with single farmhouses and lines of cypresses. Stop at a lay-by and look. They are greenest in spring and almost silver in summer.
Go when Late afternoon or morning, with low light on the clay.
Local tip There is no single stop, so drive slowly and use the lay-bys. Do not walk into the fields, which belong to farmers.
A castle of the Ricasoli family on a ridge in the heart of Chianti, with gardens, a chapel and a long view over the vineyards. Check ahead on visits.
Go when Afternoon, with time for the gardens.
Local tip Check ahead on visits and on the garden. The view from the terrace takes in a wide stretch of Chianti.
Hard almond biscuits dipped into a small glass of sweet amber dessert wine. A traditional end to a meal in Tuscany.
Local tip Dip the biscuit rather than eating it dry, which is how the Tuscans do it.
A small walled town in the Chianti hills, quiet in the evening, with a main street, a town hall and a short walk around the walls. A gentle place to end the trip.
Go when Early evening, around sunset (about 8:31 PM).
Local tip Walk the old wall, then find a table on the main street. The village is quiet after the day visitors leave.
A thick, warm soup of tomatoes, bread and basil. Plain and comforting, and a fitting last dinner.
Local tip Finish with a drizzle of new olive oil on top.
By average weather from 2021 to 2025, March to May and September to October are the most comfortable months for walking around Siena. This plan is built for mid May, which is one of the best months. Crowds and prices change through the year, so check them before you book.
It covers 5 days in Siena, planned for mid May. Each day is built around a small number of stops, with room to rest.
It was planned for most travelers. The pace and the places reflect that, so check it fits how you travel.
No. Places marked "book ahead" need a reservation. Hours, prices and availability change, so confirm before you go.
Yes. Archie drafts a day by day plan for your dates and takes your pace, the weather and who is travelling into account. You can start one from the Archie app.
Yes. It is a starting point you can change to fit your own trip: swap a place, add a day or move the pace.
Each day has about 1.1 to 44.2 kilometers between its stops, and 113.3 kilometers in all across 5 days. A short hop is a walk and a longer one a ride. Distances are straight-line estimates, so allow extra for the streets.
7 days in Florence and TuscanyAbout 60 km awayAn easy add-on
3 days of pasta and porticoes in BolognaAbout 140 km away
4 days in RomeAbout 170 km awayMake it yours in a minute, then move days around and add what you want.
A trip idea · Updated November 2026
Want your own days planned like this? Plan your own trip on the web or get the Archie app.
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