Most people picture Christmas in Italy as Rome. The tree in St. Peter’s Square, a Mass at midnight, a long lunch on the 25th. It’s lovely, and it’s only one version.
The Bolzano Christmas Market in Piazza Walther, South Tyrol, Italy, with the tiled roof and steeple of Bozen Cathedral in the background.
Photo©: Fani Kurti / istock
The question I hear every autumn is where to spend the holidays so that it feels like Italy. My answer depends on what you want December to feel like, because the season changes completely from one region to the next: carved masks in the Alps, a mountainside of lights in Umbria, papier-mâché nativity figures in the south, and the famous cities with the summer crowds gone.
I learned this firsthand. I spent a week in Venice and the Veneto in December 2024 with one of my women’s groups, and it changed how I think about winter in Italy. It’s also why I’m now planning a women’s trip to Rome and Umbria for the holidays in December 2027.
St. Mark’s Square in Venice, Italy
Photo©: Anna Fishman / Olegana Travel Boutique
Here are the places I build festive trips around, what actually happens there between early December and Epiphany, and how I put them together.
How the Italian holiday season works
Christmas in Italy is long. It opens on December 8, the Feast of the Immaculate Conception, when most towns light their trees and the markets get busy, and it runs all the way to January 6, Epiphany, when La Befana brings the children their sweets.
That gives you three distinct windows. Early December is markets and lights with fewer visitors. Christmas week is family time for Italians, so restaurants and churches are full and some shops close on the 25th and 26th. The days from New Year’s Eve to Epiphany are festive again, with concerts, fireworks and the last of the markets.
Choosing the right window matters as much as choosing the place. I usually start there.
The Christmas Market in Piazza Grande, the main square of Montepulciano, Tuscany, Italy.
Photo©: gun75 / istock
South Tyrol: Alpine Christmas, with an Italian accent
If you love the idea of a traditional Christmas market but want something less expected than Austria or Germany, this is where I send you. South Tyrol is Italian by passport and Austrian by habit, with the Dolomites standing over all of it.
Five towns hold the original Christkindl markets: Bolzano, Merano, Bressanone, Vipiteno and Brunico. Bolzano’s is the largest, Merano’s runs along the river, and Bressanone sits in the shadow of its cathedral. In 2026 most open in the last week of November and stay until January 6. Expect wooden stalls, mulled wine, apple strudel and Zelten, the dense fruit and nut bread that every South Tyrolean family seems to make differently.
The village of Santa Maddalena in the scenic Val di Funes, South Tyrol, northern Italy.
Photo©: Anastasia Gubinskaya / istock
Come in the first days of December and you may see the Krampus. Around the Feast of St. Nicholas on December 6, towns across the region hold Krampus runs, with figures in hand-carved wooden masks and sheepskins roaring through the streets. It’s theatrical, a little wild, and very old.
Skiers enjoying a sunny day on the slopes of the Dolomites in South Tyrol, surrounded by majestic mountain views.
Photo©: HAMZA YAICH / pexels
After the markets, the mountains take over. The ski season opens in early December, and South Tyrol does winter wellness better than almost anywhere in Italy: saunas with a view of the peaks, long lunches in mountain huts, and very good wine from the valleys below.
Umbria: hill towns that glow in December
Festive Christmas lights and decorations illuminating the medieval village of Gualdo Tadino in Umbria, central Italy.
Photo©: Photo Beto / istock
Umbria is the region I suggest to people who already love Tuscany. In December it’s quieter, more local, and in a few places, spectacular.
Above Gubbio, the slopes of Mount Ingino become what the Guinness World Records listed in 1991 as the largest Christmas tree in the world: more than 300 lights strung across the mountainside along 8,500 meters of cable. It’s lit at 6 p.m. on December 7 and stays on every evening through the Sunday after Epiphany. Down on Lake Trasimeno, Castiglione del Lago builds another tree of light directly on the water.
A festive Christmas market in Umbria, Italy, illuminated by warm evening lights.
Photo©: Eugenia Sol / pexels
In Perugia, the Christmas market moves underground into the Rocca Paolina, a sixteenth-century papal fortress built over a medieval street that you can still walk through. And at the end of the year, Orvieto hosts Umbria Jazz Winter, five days of jazz, gospel and soul in the old town. The 2026 edition runs from December 30 to January 3, which makes it one of the best reasons I know to spend New Year’s in Italy.
Umbria in December is the reason I’m planning our December 2027 women’s group trip around it, with Rome. It’s still taking shape. If you’d like to hear first, message me and I’ll add you to the list.
Salento: a Baroque Christmas in the heel of Italy
Baroque Christmas decorations at the Church of Santi Pietro e Paolo in Galatina, Salento, Italy.
Photo©: Fabiomichelecapelli / istock
Most people know Salento as a summer place. The beaches, the long lunches, the white towns. In December it belongs to the people who live there, and its Christmas is rooted in craft and faith.
Lecce, the Baroque city at its center, is famous for papier-mâché and for the artisans who make nativity figures by hand. Each December the Fiera dei Pupi brings the master figure makers together in the historic center, usually through the first three weeks of the month, and the stalls around Piazza Sant’Oronzo fill with local craft.
A colorful souvenir shop in Gallipoli, Salento, Italy.
Photo©: Betty Göbel / pexels
Then there are the living nativities. In Tricase, more than 200 residents stage one across the rocky hillside of Monte Orco on select evenings from Christmas Day to Epiphany, ending on January 6 with the Three Wise Men arriving on horseback. Smaller versions appear in villages all over the peninsula. It’s not a performance for visitors; it’s a town telling its own story.
Salento is also the end of the line for my Puglia food trips, so if you know the region from a spring or autumn visit, December shows you a completely different side of it.
Genoa and the Riviera: December by the sea
Porto Antico in Genoa, Italy, beautifully illuminated with festive Christmas decorations.
Photo©: Olha Gubachova / istock
Genoa gives Christmas on the Riviera its own rhythm. The tree goes up in Piazza De Ferrari, the markets open in the old center, and in the days before Christmas the city holds the Confeugo, a ceremony that goes back centuries. The Abbot of the People presents a laurel trunk to the Doge, today the mayor, and it’s set alight to wish the city good fortune in the year ahead.
For a base, I like Nervi, a few minutes east of the city, with its seaside promenade and parks. You get the festive atmosphere of Genoa during the day and the quiet of the coast at night. If the Riviera appeals beyond December, I’ve written about the western Ligurian coast and why it’s the part of the Riviera I steer people toward.
The great cities in December
The cities belong on this list too. If you already know them, December is the best excuse I know to go back; if you don’t, it’s a quieter first visit than any summer could give you.
Milan
A Christmas tree in Piazza del Duomo in front of Milan Cathedral during winter.
Photo©: Marco_Bonfanti / istock
Celebrates its patron saint, Sant’Ambrogio, on December 7. The same day, La Scala opens its opera season, and around the Castello Sforzesco the Oh Bej Oh Bej fair, a tradition about five centuries old, fills the streets with crafts, roasted chestnuts and panettone, which was born here. I’ve written more about luxury Milan if the city is new to you.
Florence
The festive Christmas market in Piazza Santa Croce, Florence, Italy, filled with visitors browsing the holiday stalls.
Photo©: Chalffy / istock
Puts up its Christmas market in Piazza Santa Croce, with wooden stalls of artisan goods and seasonal food in front of the basilica. Rome has its market in Piazza Navona, nativity scenes in churches across the city, and the tree and nativity in St. Peter’s Square.
Venice
A Christmas tree in St. Mark’s Square, Venice, with Doge’s Palace and St. Mark’s Basilica in the background.
Photo©: Chalffy / istock
Venice is the city I know best in winter. When I was there with my group in December 2024, the summer crowds were long gone and we had the city and the Veneto countryside largely to ourselves. The year ends with the annual New Year’s concert at Teatro La Fenice. We’re taking a group back to Venice and the Veneto in April 2027, and a few rooms are still open.
Thinking about Christmas in Italy?
Tell me who’s traveling, which window you have in mind, and whether you want markets, mountains, music or the sea. I’ll build the days around it.
Email anna@oleganatravelboutique.com, call (917) 345-5792, or book a planning call.
“Anna was able to pull off a magical trip for us to North Italy at the last minute. Her recommendations, suggestions were all on point as she really tries to get to know you before planning an itinerary.”
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When to go
Christmas lights and decorations illuminating a main street in Florence, Italy, at night after the rain.
Photo©: Fani Kurti / istock
Early December: markets and lights
From the last days of November to December 8 is my favorite window for first-timers. The markets in South Tyrol are open, Milan has Sant’Ambrogio and the opening of La Scala, and the trees in Gubbio and on Lake Trasimeno light up on December 7. Hotels are calmer than at Christmas itself.
A cobblestone alley decorated with festive Christmas candy ornaments and garlands in a historic Italian town.
Photo©: Magda Ehlers / pexels
Christmas week: Italy at home
This is when Italians are with their families, and it’s the most intimate time to be here. Midnight Mass, the living nativities in Salento, long lunches. Plan around December 25 and 26, when many shops and some restaurants close, and book the Christmas Eve and Christmas Day meals well ahead.
New Year to Epiphany: music and fireworks
Umbria Jazz Winter in Orvieto, the New Year’s concert at La Fenice, and the last of the markets until January 6. This window works beautifully for families, because school holidays and Epiphany line up.
If you’re weighing December against other months, I’ve put together a guide to where to travel every month of the year.
A festive week I’d build: Milan to the Dolomites
Here’s the shape of an early-December trip I love, for couples or a small family. It’s a sample to show the rhythm, not a fixed itinerary.
Days 1 - 3, Milan:
Arrive in time for Sant’Ambrogio. Walk the Oh Bej Oh Bej fair around the castle, eat panettone where it was invented, and spend an evening at La Scala if the program suits you.
Photo©: Flavio Vallenari / istock
Days 4 to 7, South Tyrol:
A private transfer north to Merano or Bressanone, with one base for the rest of the week. A day for the Bolzano market, a day for Merano, a morning in the mountains with lunch at a hut, and an afternoon in the spa. If your dates fall right, the Krampus run on the evening of December 5 or 6.
Photo©: Juergen Sack / istock
Day 8, home:
A transfer back to Milan or to Verona for your flight, or a few extra nights in Venice before New Year.
Photo©: luana rigolli / istock
For a Christmas week trip, I’d build it the other way around: Rome for the city’s nativities and St. Peter’s, then Umbria for Gubbio’s tree, Perugia’s underground market and a quiet country estate, ending in Orvieto for New Year’s and the jazz. It’s close to the shape I’m planning for our December 2027 women’s trip. You can see more of how I build Italy on my Italy itineraries page.
Who this trip is for
Couples who want December to feel like an occasion.
An anniversary, a milestone birthday, or simply a reason to go somewhere beautiful when home is gray. Milan and South Tyrol, or Venice for New Year’s.
Photo©: Anna Fishman / Olegana Travel Boutique
Families on winter break.
Markets, lights, skating and Epiphany sweets from La Befana. South Tyrol and the cities work best; I plan around early bedtimes and keep the travel days short.
Photo©: Anna Fishman / Olegana Travel Boutique
Three generations together.
Grandparents who want to give the family a holiday they’ll talk about for years. A private driver, one or two bases, and a Christmas lunch booked months ahead.
Photo©: Anna Fishman / Olegana Travel Boutique
Travelers who already know Italy.
If you’ve done Rome, Florence and Venice in the spring, December is how you see them again for the first time.
Photo©: Anna Fishman / Olegana Travel Boutique
And if you’d rather travel with a small group of women than plan a trip of your own, my women’s group trips run in spring and autumn, including one through the Dolomites and Lake Garda in September 2027. We’re also planning a holiday trip to Rome and Umbria for December 2027.
Connecting destinations
A festive trip doesn’t have to be all markets. South Tyrol pairs naturally with Venice or Verona, both a few hours away. Umbria sits between Rome and Florence, so it slips easily into a longer trip. Salento combines well with a few nights in Rome, a short flight north. And Genoa is close enough to Milan to do both in one week.
If December isn’t possible this year, the same regions are wonderful in spring and autumn. That’s when I take my women’s groups to the Veneto and to Puglia, and when the cooking classes in Italy I recommend most are running.
Why work with a luxury travel advisor for the holidays
Palazzo Pubblico and Torre del Mangia in Piazza del Campo, Siena, Tuscany, Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
Christmas is the hardest time of year to plan in Italy, because so much depends on dates. Which markets are open on the 26th. Which restaurants close for the family lunch on the 25th. Whether the Krampus run falls on your evening in Merano. Whether the train runs on New Year’s Day.
That’s the work I do before you ever pack. I know which hotels are worth it in December and which feel empty, which guides make a Christmas market more than a shopping trip, and how to get you a table for Christmas lunch somewhere that still cooks the way a nonna would.
It’s why Olegana Travel Boutique plans trips around a conversation, and why my custom trips start with what you want the holidays to feel like.
Anna Fishman, the visionary and soulful force behind Olegana Travel Boutique, orchestrates transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
Ready to plan Christmas in Italy?
This December or next, tell me which window you have in mind and who’s coming. I’ll take it from there.
Email: anna@oleganatravelboutique.com
Call: (917) 345-5792
Book a planning call
Frequently asked questions
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Yes, especially if you choose the region carefully. The markets, lights, music and food are at their best from early December to Epiphany, and many places are far quieter than in summer.
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South Tyrol has the most traditional ones, in Bolzano, Merano, Bressanone, Vipiteno and Brunico. For something different, Perugia’s market inside the Rocca Paolina, Lecce’s Fiera dei Pupi, Milan’s Oh Bej Oh Bej and Florence’s market in Piazza Santa Croce are all worth planning around.
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Many shops and museums close on December 25 and some on the 26th, and restaurants that open are often fully booked for family lunches. I plan those two days carefully and reserve your meals well in advance.
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Most open in the last week of November or around December 8 and close between Christmas and January 6. The 2026 dates for South Tyrol’s main markets run from late November to January 6.
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Cold and often snowy in South Tyrol and the Alps, crisp in Milan and Umbria, and mild in Salento and on the Riviera. I build the days around the weather in each place.
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Very. Venice has the New Year’s concert at La Fenice, Orvieto has Umbria Jazz Winter, and every city has fireworks. The days after are quiet and lovely.
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For Christmas week and New Year’s, six months or more is ideal, because the best rooms and restaurant tables go first. Early December can sometimes be arranged closer in, so it’s worth asking even if this year feels late.
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Most travelers fly into Milan, Venice or Rome. Seasonal nonstop service from the United States exists on several routes and changes from year to year, so check with your airline. I arrange the transfers and trains from there.