Photo by Intrepid on Unsplash
The 5-day plan, rearranged for 4 days: the best-ranked places stay, and each day keeps to one part of town.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
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.
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 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.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
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.
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 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.
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.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
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 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.
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.
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.
Built from the plan’s must-sees, grouped so each day stays close together and ordered by time of day.
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.
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 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 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.
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.
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 4 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 25.9 to 69.8 kilometers between its stops, and 206.8 kilometers in all across 4 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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