Residents decorate a glowing Christmas tree in a festive historic town square.
My Christmas guide for 2026–27: hill towns dressed for the holidays, markets worth a detour, old traditions, and a warm welcome at Grove Cottage.
There is something about an Italian hill town at Christmas that makes you forgive the cold. The lights go on above the narrow streets, the shop windows fill with things you suddenly feel you cannot live without, and a quick afternoon outing begins to look suspiciously like dinner. Here in Umbria, with Tuscany just across the hills, we have rather a lot of opportunities to fall into that trap.
Christmas brings another side of this landscape into view. Olive trees turn silver beneath a winter sky, the valleys disappear into morning mist, and the old brick and stone of our towns seem made for candlelight. Then there is the food: market stalls to investigate, bottles to bring home, and enough festive baking to make any sensible person postpone their resolutions until February.
This year’s guide brings together the places I love sharing around Città della Pieve, along with a few adventures further afield. Some call for an afternoon and a good pair of shoes; others deserve a night or two added to your Italian holiday. Make Grove Cottage your base for Umbria and southern Tuscany, choose the outings that appeal, and leave yourself time to enjoy being here. Nobody should spend Christmas racing through a checklist.
Naturally, I am starting with Città della Pieve. I live here, so a little favoritism is allowed. Our red-brick town is lovely in every season, but Christmas gives its lanes and little squares a particular warmth. Come for a wander, stop for coffee, investigate the shops, and stay for lunch. By the time evening arrives, you will have a very good reason to take another turn through town.
One tradition to look out for is the Monumental Presepe, created by the Terziere Castello in the underground spaces of Palazzo della Corgna. The setting is part of the appeal: you leave the street behind and enter a different world beneath the town. The local Christmas page and presepe organizer are the places to check for the new program. As of 10 November, I have not verified the 2026–27 opening dates, so last year’s tree-lighting times and nativity schedule have been left out.
At Castiglione del Lago, Christmas has the advantage of an enormous expanse of water to play with. Luci sul Trasimeno is known for the great Christmas-tree design laid out across the lake, a sight best enjoyed after dark when the lights take possession of the view. Arrive earlier for a stroll through town and something to eat, then give the evening over to the lake.
Umbria Tourism lists the 2026–27 season from 5 December to 6 January. The event website has the practical details for the viewing route, tickets, and individual attractions. Wrap up properly: a lakeside evening in December is an excellent argument for bringing the scarf you thought you would not need.
Orvieto makes a wonderfully indulgent winter day out. Give the cathedral the time it deserves, wander through the old streets, and find somewhere for a proper lunch. It is a city where art, architecture, and the prospect of another course can very happily occupy the same afternoon.
If you are staying through New Year, Umbria Jazz Winter runs from 30 December 2026 to 3 January 2027. Choose your concerts before you travel and build the day around them. Good music, a beautiful city, and dinner afterwards strike me as a very civilized way of seeing one year out and another in. The festival dates are confirmed; other Christmas attractions should be checked separately through Orvieto’s visitor information.
Assisi deserves a place in any Umbrian Christmas journey. The basilicas, pale stone, and streets climbing above the valley give the visit a different pace, and there is pleasure in letting the day unfold between a church, a small shop, and somewhere warm to sit. Give yourself time to look properly; Assisi rewards more than a photograph taken on the way back to the car.
The town’s connection with Saint Francis gives its Christmas traditions particular meaning. For this season, the municipality has published preparations for the Christmas markets, though I have not verified a complete public program for 2026–27. Check the Comune di Assisi for current dates before planning around a particular market, nativity, or light display.
Spello is a lovely companion to an Assisi outing, especially if you enjoy a town best on foot, with no great urgency about reaching the next corner. Allow time for its lanes, a meal, and a little browsing. In winter, the pleasures of these small towns are often the simplest ones: a beautiful doorway, a quiet square, the discovery of a shop you had walked straight past.
Keep an eye out for Spello Splendens, the festival devoted to medieval and traditional Christmas music, including the distinctive sounds of bagpipes and zampogne. The organizer’s published program currently refers to December 2025 and January 2026; the next edition’s dates are not yet verified. It is worth checking again closer to your visit if music is part of your Christmas wish list.
Montepulciano knows how to give a Christmas market a setting. Piazza Grande and the surrounding streets provide the stonework and grandeur; the wooden stalls supply decorations, gifts, and plenty of temptation for anyone who came out without lunch. Take the uphill walk at your own pace, browse the market, and stay long enough to see the square after dark.
Natale a Montepulciano advertises its season from 21 November 2026 to 6 January 2027, with selected opening days before the daily Christmas run beginning on 19 December. The market and Santa’s Castle have separate arrangements, so check the attraction you intend to visit. My suggestion is to leave a little space in the shopping bag for something edible. A Christmas ornament is lovely, but it does very little for you at teatime.
Pienza is an easy town to fall for: a handsome square, little streets to wander, and food shops capable of making a perfectly respectable adult abandon all restraint. Christmas adds another reason to visit. The Pro Loco’s 2026 calendar lists Christmas markets on 5–8 December, with food, entertainment, and festive activities in the historic center.
Then comes the Torneo del Panforte, scheduled for 26–30 December beneath the town hall’s loggias. Yes, the Christmas cake has a sporting life here. It is a longstanding local game involving tossing the wrapped panforte along a table, and it is quite a departure from the usual question of who wants another slice. The junior tournament is listed for 2–3 January 2027. Go for the town, stay for the competition, and buy a panforte of your own to treat more conventionally.
Arezzo is a good choice when you want a full day of Christmas activity with plenty of art and shopping around the edges. Start before dark, spend some time in the historic center, and let the evening bring you back towards Piazza Grande. There is something particularly satisfying about seeing an old square change character as the illuminations come on.
Arezzo Città del Natale runs from 14 November 2026 to 6 January 2027, but the Tyrolean market in Piazza Grande finishes on 27 December. It opens Thursday to Sunday before 17 December, with extra openings on 7–8 December, then daily from 17–27 December. Keep that distinction in mind if you are visiting after Christmas: the wider festivities continue into January, while the market has its own closing date.
Cortona may be forever associated with the Tuscan sun, but there is plenty to enjoy with your coat on. Its sloping streets and piazzas make a fine winter wander, with shops, cafés, and views to interrupt the climb. Start around Piazza della Repubblica and leave yourself time to explore beyond the first attractive window.
Previous Christmas editions have included projections, artisan markets, and nativity displays, but the official Natale a Cortona website still carries the 2025–26 program at the time of this update. The 2026–27 dates and attractions remain unverified. Cortona stays firmly on my list; the old calendar does not. Check the organizer’s new announcements before booking a visit around a particular event.
Spoleto offers plenty to occupy a winter outing before you even reach the Christmas stalls. Make time for a walk through town, then head to Piazza Garibaldi, where this year’s market brings together craftwork, decorations, and Umbrian food and wine. It is a good opportunity to find presents that will actually be enjoyed rather than politely stored in a cupboard.
The municipality confirms the market on selected dates between 5 December 2026 and 6 January 2027. Opening days are 5–8, 11–13, 18–20, 25–27, and 31 December, then 1–6 January, with listed market hours of 10.30am–7.30pm. The opening celebration is scheduled for 5 December at 5pm, and the program includes Santa’s house and children’s activities. Check the linked notice for the day’s details.
Gubbio takes the Christmas tree into an entirely different category. Lights spread up Mount Ingino to form an immense tree above the town, giving you a very good reason to stay after sunset. Make a day of it: explore the medieval streets, have lunch, and leave the big reveal until the sky is dark.
The market in Piazza Quaranta Martiri opens 21–22 and 28–29 November, 5–8 and 12–13 December, and then daily from 19 December 2026 to 6 January 2027. Usual hours are 10am–8pm, with a 3pm opening on Christmas Day and New Year’s Day. The mountainside tree has a different calendar: 7 December 2026–10 January 2027. Visit from 7 December if you want to combine the two.
Empoli throws itself into Christmas with the sort of enthusiasm that makes a family outing easy to plan. The historic centre becomes the focus of lights, attractions and festive activity, while the market stalls offer crafts, food and gifts. It is worth considering as part of a longer Tuscan trip, particularly if you are already including Florence.
Empoli Città del Natale runs from 14 November 2026 to 10 January 2027, but the Christmas markets finish on 24 December. Their listed opening days are 14–15, 21–22 and 28–29 November; 5–8, 12–13, 19–20 and 22–24 December, from 9am–8pm. Choose your dates according to what you want to see; the market and the full festive programme are not the same calendar.
Todi is a lovely choice for anyone who likes their Christmas outing to include a beautiful square and an unhurried meal. Spend some time around Piazza del Popolo, take a walk through the centre and resist the urge to squeeze another town into the afternoon. These places deserve a little attention, especially when winter gives you the excuse to stop indoors.
The complete 2026–27 town programme is not yet verified, but there are already musical dates to consider. La Consolazione ETAB lists a Christmas concert with the A.Gi.Mus youth chamber orchestra and University of Perugia choir on 13 December at 9pm, and the Silvia Aprile Trio on 19 December at 9pm, both at the Church of the Consolazione. Check ETAB’s announcements and the municipal events pages for details and further additions.
For a Christmas Eve with a strong sense of place, look towards Abbadia San Salvatore on Monte Amiata. Here the fiaccole bring people into the streets around great stacks of burning wood, with traditional singing and the warmth of the fires at the heart of the evening. It is a celebration shaped by the town and the people who keep it going.
Visit Tuscany lists the fiaccole for 24 December 2026. Plan the evening around the local programme and think through the return journey before you leave. This is a mountain outing in winter, so allow for the weather and road conditions. Arrive properly dressed and ready to spend time outside; the atmosphere is worth more than a hurried photograph.
A little further afield, Candelara offers one of the most appealing ideas in the Christmas calendar: at set times, the electric lights go out and candles take over. The medieval village near Pesaro becomes the setting for a market devoted to candlelight, with that softer glow changing the whole feeling of the streets. I would make this part of an overnight visit to Le Marche rather than squeeze it into a rushed return trip.
The provincial Pro Loco network lists Candele a Candelara on 28–29 November and 5–8, 12–13 and 19–20 December 2026, with the scheduled switch-offs at 5.30pm and 6.30pm. Check the organisers for tickets, transport arrangements and any changes before travelling.
Florence is the obvious temptation when you want to add a city day to your holiday. The Weihnachtsmarkt in Piazza Santa Croce runs from 14 November to 20 December 2026, bringing European crafts and festive food to the square. Browse, eat something warm and give yourself time for the city beyond the stalls. Florence has a habit of making an afternoon disappear.
This market closes before Christmas itself, so plan an Advent visit if it is high on your list. For a rail outing from our area, look at services from Chiusi–Chianciano Terme and arrange your transfer to the station; Città della Pieve does not have a station in the historic centre. Check the return timetable before committing to dinner. Romance is all very well, but it will not bring back the last train.
Lucca is the extra stop I would consider if your Tuscan Christmas travels have room to stretch. Take time for the old town, its shops and squares, then let the Christmas market become part of the day rather than the entire purpose of it. Staying overnight gives you the pleasure of the evening without watching the clock for a long drive back.
Lucca’s tourism office lists the Piazza Napoleone Christmas market from 22 November 2026 to 6 January 2027. Other markets and activities have their own dates within the wider programme, so check the calendar for the days you are visiting.
Rome earns its place as a city extension to an Umbrian holiday. Give yourself time for its churches, nativity displays and a wander through the centre, then settle somewhere for dinner. I would not promise you empty streets at Christmas; this is Rome, and quite a few other people have had the same excellent idea.
Roma Capitale’s current notice places the Festa della Befana in Piazza Navona between 1 December 2026 and 6 January 2027, with the detailed activities developing within that period. Follow the city’s announcement and Turismo Roma for the public programme. If a Christmas service or a particular festive meal is important to your trip, confirm arrangements well ahead.
Milan gives Christmas a handsome urban setting, with the Duomo, the Galleria and more opportunities to shop than anyone strictly needs. It is also an excellent place to take panettone seriously. Buy a good one, have another coffee and consider the walking you have done an adequate contribution to the day’s exercise.
YesMilano confirms the Piazza Duomo market from 1 December 2026 to 6 January 2027, daily from 9am–9pm. Add Milan as a separate stay on a longer Italian journey, with time for the city around the festivities. If you fancy a performance at La Scala, check its actual programme and book the event you want rather than assume a Christmas concert will fit your dates.
Piedmont is another fine excuse to extend the holiday northwards. Il Magico Paese di Natale has its 2026 season from 14 November to 20 December, with different opening days across its locations. Asti hosts the large market, while Govone brings Christmas activities and stalls to the setting around its royal castle. Check the organiser’s calendar for the place and date you want; the two are not interchangeable.
Turin supplies a different sort of spectacle. Luci d’Artista runs from 23 October 2026 to 10 January 2027, turning an evening walk into a route through illuminated works of art. Leave time for a café stop and a bicerin, the city’s layered combination of coffee, chocolate and cream. It is a very agreeable way of recovering from a cold evening.
For those continuing towards the mountains, Cuneo, Limone Piemonte and Sestriere remain ideas for a separate Alpine leg of the journey. Choose the resort and dates around current snow, lift and road information. Snow is a lovely Christmas accessory, but it has never been especially obedient about reservations.
A little planning leaves more time for enjoying yourself. These are the published dates checked for this guide; a season running between two dates does not necessarily mean that every attraction opens daily.
| Place or event | Dates | What to check |
|---|---|---|
| Arezzo — Città del Natale | 14 November–6 January | Individual attraction calendars vary. |
| Arezzo — Tyrolean market | 14 November–27 December | Selected days, then daily from 17 December. |
| Florence — Santa Croce market | 14 November–20 December | Closes before Christmas. |
| Empoli — full festive programme | 14 November–10 January | Markets finish 24 December, on selected days. |
| Asti and Govone | 14 November–20 December | Different opening days at each location. |
| Montepulciano | 21 November–6 January | Selected days; daily from 19 December. |
| Gubbio — market | 21 November–6 January | Selected days; daily from 19 December. |
| Lucca — Piazza Napoleone market | 22 November–6 January | Check local hours and activities. |
| Candelara | 28–29 November; 5–8, 12–13, 19–20 December | Tickets and transport arrangements. |
| Milan — Piazza Duomo market | 1 December–6 January | Listed daily, 9am–9pm. |
| Rome — Piazza Navona festivities | 1 December–6 January | Detailed programme still developing. |
| Pienza — markets | 5–8 December | Panforte tournament follows 26–30 December. |
| Spoleto — Piazza Garibaldi market | 5 December–6 January | Selected days listed in the Spoleto section. |
| Luci sul Trasimeno | 5 December–6 January | Viewing route and attraction calendars. |
| Gubbio — mountainside tree | 7 December–10 January | Separate from the market calendar. |
| Todi — Consolazione concerts | 13 and 19 December, 9pm | Confirm programme and access with ETAB. |
| Abbadia San Salvatore — fiaccole | 24 December | Evening programme and winter travel. |
| Orvieto — Umbria Jazz Winter | 30 December–3 January | Concert tickets and venues. |
| Turin — Luci d’Artista | 23 October–10 January | Use the official installation map. |
November and December dates refer to 2026; January dates refer to 2027. Città della Pieve, Assisi, Spello Splendens and Cortona still need confirmed 2026–27 schedules; Todi’s complete town programme also remains unverified.
After a day of markets, church bells and cobbled streets, there is a great deal to be said for coming home to a place of your own. Our Grove Cottage in Città della Pieve is a private holiday home with its own garden and grounds, a well-equipped kitchen and a wood burner for winter evenings. The town is within walking distance, and the cottage makes a comfortable base for exploring Umbria and southern Tuscany.
Spend the morning shopping for ingredients and make lunch at home, or head out to one of the towns in this guide and return with a market bag full of good intentions. There is no obligation to go anywhere every day. Put another log on, open the bottle you bought and cut the panettone properly. Thin slices are a miserable way to celebrate Christmas.
We would love to welcome you and share this corner of Italy at a time of year that deserves far more attention. Check your Christmas dates and book Grove Cottage, and give yourself time for the towns, the food and the pleasure of settling in. Buon Natale a tutti!
Updated 10 November 2026. Check the linked organisers before travelling for opening days, tickets, and programme changes. Reserve festive meals ahead. A car is useful for the regional outings; Florence and Rome need a considered travel plan, while Le Marche and northern Italy are best treated as extensions with overnight stays.
A curious adventurer living la dolce vita, creating insightful stories as a freelance writer, content creator, and printmaker, guiding you through the exquisite world of fine food, wine, art, and all things Italian.
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