Milan might not be the first place that comes to mind when you're looking for Christmas markets, but a Christmas markets Milan holiday is one of the most rewarding festive breaks I plan.
In December, the city feels wonderfully festive. Stalls fill the streets around the Duomo, the Galleria Vittorio Emanuele II is decorated for Christmas and you can try panettone in the city where it was first created.
What makes this holiday really special, though, is the journey into the Swiss Alps. You'll spend time in St Moritz before boarding the Bernina Express for a spectacular train journey through the mountains to Tirano.
I've brought the two experiences together in a four-night trip that gives you enough time to enjoy Milan without rushing, as well as a full day in Switzerland.
Prices start from £969 per person, including return flights, private airport transfers, four nights in Milan and the full-day St Moritz and Bernina Express experience with a guaranteed panoramic carriage.
Based on two adults sharing at Maison Borella on selected December 2026 departures. Prices are live and subject to availability.
In This Guide
Your Holiday at a Glance
- Duration: Four nights
- Destination: Milan, with a full-day visit to St Moritz
- Travel dates: Selected December 2026 departures
- Accommodation: A choice of five handpicked Milan hotels
- Main experience: St Moritz and the panoramic Bernina Express
- Price: From £969 per person
This Christmas markets Milan holiday would be lovely for couples or friends who enjoy city breaks but would like something a little more memorable than a weekend spent solely visiting Christmas markets.
Your 4-Night Itinerary
Day 1: Fly to Milan
Fly from your chosen UK airport, with a private transfer waiting to take you directly to your hotel.
Once you've settled in, the rest of the day is yours. You might like to take a gentle walk through the surrounding neighbourhood before finding somewhere welcoming for your first Italian aperitivo.
Day 2: Milan's Christmas Markets
Your first full day is for exploring Milan and its Christmas markets.
Start around Piazza del Duomo, where festive stalls fill the streets beneath the cathedral's marble spires. From here, you can wander through the Galleria Vittorio Emanuele II to see its beautiful Christmas displays before continuing towards Brera or Sforza Castle.
If your holiday coincides with Oh Bej! Oh Bej!, you'll also be able to visit this historic market beside the castle. Unlike Milan's other Christmas markets, it only takes place for around four days surrounding the Feast of Sant'Ambrogio on 7 December. The anticipated dates for 2026 are 5 to 8 December, subject to official confirmation.
There's no need to plan every minute of the day. Leave yourself time for coffee, lunch and anything interesting you happen to find along the way.
Day 3: St Moritz and the Bernina Express
An early start for the highlight of the holiday.
You'll travel by comfortable coach from Milan into Switzerland, arriving in St Moritz with around two and a half hours to explore.
That gives you enough time for a walk beside Lake St Moritz, a look around the town's boutiques and somewhere cosy for lunch or a hot chocolate. You could also try an Engadine nut tart, a local pastry filled with caramelised walnuts.
In the afternoon, you'll board the Bernina Express for the journey through the Alps to Tirano. Your place in a panoramic carriage is guaranteed, with oversized windows giving you a much wider view of the mountains, lakes and viaducts along the route.
Once you arrive in Tirano, you'll return to Milan by coach later in the evening.
The complete excursion lasts approximately 12½ hours. It's a long day, and I think it's important to be clear about that, but the scenery makes it an incredibly memorable one.
Day 4: More Time in Milan
After your day in the Alps, you'll have another full day to enjoy Milan at a gentler pace.
You could visit the Duomo and walk among its rooftop spires, explore the cobbled streets and galleries of Brera or see Leonardo da Vinci's Last Supper. Tickets for The Last Supper are limited, so this is one to arrange well ahead.
If you'd prefer a slower day, spend some time shopping before heading to the Navigli canals for drinks and dinner. It's one of Milan's liveliest areas for aperitivo, with independent restaurants and bars lining the water.
Day 5: Fly Home
Enjoy breakfast and perhaps one final Italian coffee before your private transfer to the airport for your flight home.
Where to Stay in Milan
There are five hotels to choose from, ranging from landmark five-star stays to a more economical option beside the Navigli canals.
The right one for you will depend on whether location, hotel facilities, individual character or overall price matters most.
Five-Star Hotels
Palazzo Cordusio, a Gran Meliá Hotel
Palazzo Cordusio occupies a beautifully restored 19th-century building on one of Milan's grandest central squares.
Its location is difficult to beat. You'll be close to the Duomo, Galleria Vittorio Emanuele II and La Scala, so you can explore the main sights and central Christmas market easily on foot.
The hotel's restaurants and rooftop terrace also make it somewhere you'll enjoy returning to at the end of the day.
Best for: Five-star luxury, rooftop views and an exceptional central location.
Chateau Monfort
Chateau Monfort is the one to choose if you'd like somewhere a little different.
Inspired by fairy tales, opera and fantasy, it has imaginative interiors and individually styled rooms. There's also a spa, which will be particularly inviting after a cold day exploring Milan.
It's close to the fashion quarter rather than directly beside the Duomo, but still well placed for seeing the city.
Best for: A romantic stay with personality, beautiful interiors and a spa.
Four-Star Hotels
Matilde Boutique Hotel
Matilde Boutique Hotel is just moments from the Duomo, placing you right in the heart of Milan.
It feels stylish and special without being overly formal, with thoughtful details and a more intimate atmosphere than the city's larger hotels.
Its position is particularly convenient if you'd like to be close to the main Christmas market and return to your hotel easily during the day.
Best for: Boutique style and being exceptionally close to the markets and main sights.
Hotel Spadari al Duomo
Hotel Spadari al Duomo is a warm and welcoming hotel within a short walk of the cathedral.
The interiors feature work by contemporary artists, but it's the friendly and personal service that really makes this hotel stand out. It's a lovely choice if you want to stay centrally while having somewhere a little quieter to return to.
Best for: Personal service, original artwork and a relaxed boutique atmosphere.
Maison Borella
Maison Borella sits directly beside the Naviglio Grande in one of Milan's most atmospheric neighbourhoods.
Set within an 18th-century building, it combines original character with modern comfort. Step outside and you'll find canalside restaurants, independent shops and some of the city's liveliest aperitivo bars.
It's further from the main Christmas markets than the other hotels, at around a 25 to 30-minute walk from the Duomo or a short journey by public transport. This less central location helps make it the most economical of the five options and is why it has been used for the starting price of £969 per person.
Best for: Character, canalside evenings and better value if you don't mind travelling a little further to the markets.
Not sure which hotel feels right? Tell me what matters most to you and I'll happily talk you through the differences.
Milan's Christmas Markets
What sets the Christmas markets Milan offers apart from other European destinations is how they're woven into the fabric of the city rather than gathered within one enormous market.
This means you can combine the stalls with Milan's architecture, neighbourhoods, cafés and shops, rather than spending the whole trip in one very busy market square.
Oh Bej! Oh Bej!
Oh Bej! Oh Bej! is Milan's oldest and most traditional Christmas market, but it's important to know that it doesn't run throughout December.
The market takes place for around four days surrounding the Feast of Sant'Ambrogio on 7 December. The anticipated dates for 2026 are 5 to 8 December, although these are subject to official confirmation.
Held around Sforza Castle, the market's stalls sell crafts, decorations, antiques, food and seasonal treats. Its name roughly translates as "Oh, how lovely!", and it has been part of Milan's festive celebrations for centuries.
If you particularly want to experience Oh Bej! Oh Bej!, choose a departure that includes these dates.
Piazza del Duomo
The main Christmas market brings rows of wooden stalls to the streets surrounding Milan Cathedral.
You'll find festive food, gifts and decorations, all with the Duomo as a rather spectacular backdrop. It's easy to combine with the cathedral, rooftop terraces and Galleria Vittorio Emanuele II.
Unlike Oh Bej! Oh Bej!, the Duomo market runs for a much longer period. The 2026 market is expected to take place from 1 December 2026 until 6 January 2027.
Galleria Vittorio Emanuele II
The Galleria isn't a traditional Christmas market, but it's one of Milan's loveliest places during December.
Its soaring glass roof, designer displays and enormous Christmas tree make it feel wonderfully festive, particularly after dark. It's also a good place to warm up when the December weather becomes a little too chilly.
Navigli
Navigli offers a more relaxed alternative to the busy historic centre.
The canals are lined with independent shops, restaurants and bars, with lights reflecting across the water in the evening. The large monthly antiques market is also worth visiting if its date coincides with your stay.
The Bernina Express Experience
The Bernina Express follows one of Europe's most beautiful railway routes through the Swiss Alps.
The wider route crosses 196 bridges, passes through 55 tunnels and climbs to more than 2,250 metres above sea level. It forms part of the UNESCO-listed Rhaetian Railway landscape.
Your journey travels south from St Moritz towards Tirano. Along the way, look out for the Morteratsch Glacier valley, Alpine lakes, the Bernina Pass and the famous Brusio spiral viaduct, where the railway curves around itself as it descends.
The panoramic carriages have oversized windows extending towards the roof, allowing you to see much more of the surrounding landscape.
Snow is common in the higher sections of the route during December, but it can't be guaranteed. The shorter winter daylight hours may also reduce some of the views towards the end of the journey.
You'll need to carry your passport or valid travel identification because the excursion crosses the border between Italy and Switzerland.
What's Included
- Return flights from a selected UK airport
- Four nights at your chosen Milan hotel
- Private airport transfers in Milan
- A full-day St Moritz and Bernina Express excursion, including coach travel from Milan, around two and a half hours in St Moritz, a guaranteed place in a panoramic carriage and coach travel back to Milan from Tirano
- Financial protection
- My support before, during and after your holiday
- A personal Milan and St Moritz destination guide
Your exact flight times, baggage allowance and room type will be confirmed with your personal quotation.
Prices and Hotel Upgrades
Prices start from £969 per person, based on two adults sharing at Maison Borella on selected December 2026 departures.
Maison Borella is the most economical of the five hotels because it's situated in Navigli, a little further from the main Christmas markets.
If you'd prefer to stay closer to the Duomo or upgrade to one of the five-star hotels, I'll confirm the additional cost for your chosen dates and room type.
Prices are live and will vary depending on your departure airport, travel dates, hotel and current availability.
This is a complete four-night holiday, although extra nights can be added in Milan if you'd like to stay a little longer.
Why Plan Your Holiday With Me?
I'm Rachael. I plan tailor-made holidays for curious travellers who love comfort. New experiences, lovely places to stay and someone looking after the details.
Design
I listen first, then shape your holiday around what you enjoy and what makes you comfortable. From the route to your room, with time to explore and time to relax.
Discover
With trusted specialists and local experts, I find distinctive places to stay and experiences that help you get to know a destination, chosen around your interests.
Travel Well
I contact your hotels before you arrive, reconfirm your stay and share your preferences. I ask about upgrades and thoughtful extras where available, and support you until you're safely home.
Useful Things to Know
The Excursion Is a Long Day
The St Moritz and Bernina Express excursion lasts approximately 12½ hours, with an early departure and a late return to Milan.
It includes several hours of coach travel as well as the train journey, so it's worth making sure everyone travelling will be comfortable with a full day.
Oh Bej! Oh Bej! Is a Short Event
Milan has festive markets throughout December, but its famous Oh Bej! Oh Bej! market only takes place for around four days surrounding 7 December.
If this particular market is important to you, let me know so I can check that your holiday dates coincide with it.
December Will Be Cold
Milan will be cold in December, while temperatures in St Moritz and along the Bernina route will be lower.
Bring warm layers, a waterproof coat and comfortable footwear with good grip.
Book Milan's Main Attractions Early
Tickets for The Last Supper, the Duomo rooftop terraces and performances at La Scala can sell out.
If you'd like to include any of these, I can help you work them around the itinerary.
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Frequently Asked Questions
Is the Bernina Express included?
Yes. The holiday includes coach travel from Milan to St Moritz, approximately two and a half hours in St Moritz, the Bernina Express journey to Tirano and coach travel back to Milan.
A guaranteed place in a panoramic carriage is included.
How long is the Bernina Express excursion?
The complete excursion lasts approximately 12½ hours. It starts early and returns to Milan later in the evening.
Does the train travel both ways?
No. You'll travel by coach from Milan to St Moritz, take the Bernina Express from St Moritz to Tirano and then return to Milan by coach.
Will there definitely be snow?
Snow is common in the higher parts of the route during December, but it can't be guaranteed.
Even without fresh snowfall, the glaciers, lakes, mountain passes and viaducts make it a beautiful journey.
Is Oh Bej! Oh Bej! open throughout December?
No. Oh Bej! Oh Bej! only takes place for around four days surrounding the Feast of Sant'Ambrogio on 7 December.
The anticipated dates for 2026 are 5 to 8 December, subject to official confirmation. The main Christmas market around the Duomo runs for much longer.
Which hotel is included in the starting price?
The starting price of £969 per person is based on two adults sharing at Maison Borella.
You can choose one of the other four hotels, with the additional cost confirmed for your preferred dates.
Which hotel is closest to the Christmas markets?
Matilde Boutique Hotel and Hotel Spadari al Duomo are both very close to the Duomo and its Christmas market.
Palazzo Cordusio is also exceptionally well placed if you'd prefer a five-star stay.
Can I extend the holiday?
Yes. Although the trip is designed as a four-night holiday, additional nights can be added in Milan.