The first week of December transforms Milan in a way no other city quite manages. Streets light up, shop windows sparkle, and the air fills with the unmistakable scent of roasted chestnuts. Locals start preparing for their patron saint’s day, Sant’Ambrogio, on 7th December - a moment that marks the true beginning of Milan’s festive season.

If you’ve ever wondered when Milan feels both elegant and warm, cultural and cozy, this is it. The Sant’Ambrogio long weekend brings together three of the city’s most iconic events: the opening night of Teatro alla Scala, the historic Oh Bej! Oh Bej! fair, and the international craft celebration Artigiano in Fiera. For travelers, it’s an ideal opportunity to enjoy Milan at its most joyful and authentic.

The days around 7 December hold a special charm. Milan slows down just enough for people to enjoy the arrival of the season, yet the city’s energy remains unmistakably alive. Families stroll through the streets, cafés feel busier than usual, and the first holiday lights create a warm glow across the city.

This is also a public holiday for locals, so expect a festive atmosphere almost everywhere you go. If you love the idea of visiting a city when traditions take center stage, the Sant’Ambrogio weekend offers the perfect mix of culture, food, and holiday spirit.

Every year on Sant’Ambrogio Day, one of Italy’s most loved rituals takes place: the opening night of Teatro alla Scala’s opera season. It isn’t just a performance - it’s a cultural milestone that locals follow with pride and excitement.

In 2025, the season will open with Shostakovich’s Lady Macbeth of the Mtsensk District, conducted by Riccardo Chailly. The theater comes alive with elegance, from the glimmer of the foyer to the anticipation of the audience waiting for the first notes.

Even if you’re not attending the premiere, simply being in the city during opening week is special. Many museums and cultural institutions time their winter programs to coincide with the event, creating a broader atmosphere of celebration.

If you want to attend a show around this period, book as early as possible: December performances are among the fastest to sell out. If you love opera or ballet and you would like to include an experience at Teatro della Scala in Milan, we can help you book the tickets and plan your itinerary in the city.

A few steps from Castello Sforzesco, the historic Oh Bej! Oh Bej! fair brings more than five centuries of tradition to life. Running from 5 to 8 December, it’s one of the most loved Christmas markets in Italy (here’s our complete guide to the best Christmas Markets in Italy), and it’s easy to understand why.

Here you can wander through a lively maze of stalls offering:

• Handmade ornaments and wooden toys
• Traditional sweets and winter snacks
• Vintage finds and artisanal gifts
• Local specialties from Lombardy and beyond

The name “Oh Bej! Oh Bej!” comes from the joyful cries of children: “How nice! How nice!” - and today the fair still carries that same cheerful spirit. Early mornings are especially pleasant, allowing you to enjoy the stalls at a slower, more delightful pace.

Include a visit to the fair during a walking tour of the city.

While Oh Bej! preserves Milan’s oldest traditions, Artigiano in Fiera adds an international touch to the weekend. Held at Fiera Milano, this sprawling event gathers artisans from across Italy and around the world.

Expect:

• Regional crafts and high-quality handmade products
• Food specialties you won’t easily find elsewhere
• Jewelry, clothing, and home décor
• Live demonstrations from skilled artisans

It’s the perfect place for thoughtful holiday shopping or for simply exploring global crafts without leaving the city. The fair is easy to reach by metro (Rho Fiera on the red line), and you can spend a few hours - or an entire day - discovering one pavilion after another.

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Milan during Sant’Ambrogio is magical, and with a few simple choices you can make the most of your visit.

Try to:

• Visit Oh Bej! on a weekday morning for the most relaxing experience.
• Combine a cultural stop, like a gallery or museum, with the markets for a balanced day.
• Enjoy seasonal treats such as freshly baked panettone or a steaming cup of vin brulé.
• Walk as much as possible. Milan’s elegant streets reveal their best angles during the festive season (and if you need transportation, our private transfers are always available for you).

Reserve restaurants and performances early; December is a busy month for locals and visitors alike.

Some cities feel festive only after mid-December. Milan is not one of them. Thanks to Sant’Ambrogio, the celebrations begin early, offering a joyful and culture-rich long weekend that blends history, tradition, and modern creativity.

You’ll get to experience one of the world’s most prestigious opera debuts, wander one of Italy’s oldest Christmas markets, and explore global craftsmanship - all without the peak holiday crowds. If you’ve ever dreamed of an early-winter getaway that feels both stylish and welcoming, this weekend might be exactly what you’re looking for.

Here at Play Italy, we’re always ready to help you bring this experience to life. Our Travel Designer can design a trip that suits your pace and comfort, whether you want a cultural deep dive or a relaxed holiday escape. For more inspiration and insider tips, subscribe to our newsletter. And if you’re getting ready to book your Italian adventure, our How to Book video tutorial walks you through the process step by step.

Your Milan winter story awaits. Come play with us and make it unforgettable.

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