Now, I believe when you travel, you should always work with an advisor. I am biased! But that is never more true than when it comes to the Olympics. Working with a professional makes all the difference. We guarantee tickets, streamlined logistics, exclusive hospitality suites at arenas, and even help with dining reservations. We provide the kind of behind-the-scenes support that transforms a once-in-a-lifetime trip into a seamless, unforgettable experience.

But even with those advantages, Olympic planning comes with its quirks. Hotels often play out like a game of chicken: lock in now at sky-high rates, or gamble that inventory will open up closer to the Games. In Paris, demand for hotel rooms lagged behind expectations, so for those who waited, it worked out.

But every Olympic destination — and every event — is different, shaped by external forces that can shift quickly.

Milan–Cortina 2026 will have its own rhythm, and knowing how to play it is half the strategy.

Why the Winter Games Feel Different

Here’s the surprising truth: the Winter Olympics are only about a quarter the size of the Summer Games. Think 16 sports in Milan–Cortina versus 72 in Paris. That smaller scale means two things for travelers:

• Less frenzy than Paris 2024 — fewer tourists, fewer athletes, more breathing room.
• Pockets of scarcity — especially for hockey, figure skating, Alpine skiing finals, and luxury hotels in Cortina and Milan.

Where the Action Happens

Milan: Opening Ceremony, ice hockey, figure skating, speed skating, and short track — all the indoor ice sports plus Italy’s fashion capital as your backdrop.

Cortina d’Ampezzo: The Alpine jewel, hosting downhill and slalom skiing, and some of the most dramatic Olympic moments.

Livigno: High-altitude thrills — freestyle skiing and snowboarding with an X-Games energy.

Tesero: Cross-country skiing in the heart of Val di Fiemme, known for its Nordic heritage.

Predazzo: Ski jumping and Nordic combined — gravity-defying feats with breathtaking Dolomite scenery.

Bormio: Alpine skiing speed events (downhill, super-G), held on legendary runs that regularly host the World Cup.

Anterselva (Antholz): Biathlon — a dramatic blend of endurance skiing and precision marksmanship.

Verona: a Closing Ceremony promised to be a spectacular finale in Verona’s historic Roman arena.

The Two Pathways to Experience It

As with most Olympic Games, access comes down to two choices:

1. Hospitality Tickets (à la carte)

Choose your tailored adventure. Every ticket includes premium lounge access with food, drinks, and a bar. There are no “bare-bones” tickets — every seat comes with hospitality built in.

2. Turnkey Packages (all-inclusive)

For travelers who want ease above all else. Packages bundle hotel, tickets, breakfast, daily transport, and on-site staff support. Transport usually means the elevated metro system created for the Games. I can, of course, add private drivers. Packages can also span multiple clusters (Milan + Cortina + Livigno), for a broader Olympic journey.

Hotels: What to Expect

• Minimum stays are real. Cortina often requires 7–10 nights, and Milan properties are following suit. These minimum requirements make it challenging to see different sports across northern Italy.
• Four-star hotels are the standard in packaged offers.
• Five-star and Palace hotels (Four Seasons, Portrait, Bulgari) sit in a premium tier, accessible now only via special packages.
• In Paris, a colleague secured the Peninsula just three months out when inventory opened unexpectedly — though it could have been only a €10,000-per-night suite. Lesson: nothing is ever certain, and timing is everything.
• Insider note: The much-anticipated Mandarin Oriental Cortina has been delayed, tightening luxury supply in the Dolomites.

Insider Tips for the Winter Olympics 2026 in Milan–Cortina

• Patience can pay. “Sold out” doesn’t always mean gone forever — watch for inventory releases closer to the Games.
• Milan is the anchor. With the opening ceremony, hockey, and figure skating, it offers the richest mix of sports and the best hotel base.
• Cortina is scarce. Expect strict minimum stays and limited luxury inventory, especially with the Mandarin Oriental delayed.
• Livigno = energy. A magnet for high-energy sports.  

Smart Strategy: Patience + Precision

Booking the Olympics is a delicate balance between securing early commitments and waiting for the right release. Our partner currently holds significant inventory, but history indicates that options often become available closer to the Games. The key is knowing when to move and having someone monitor the shifts in real time. And how strong the steel in your stomach is!

You can attend the Olympics without going all out. Some of our packages include solid 4-star hotels that are well-located. And there are many ticket tiers.

If you’re interested, do reach out! These Olympics are sure to be special. (You could also swing by Venice on the way in and experience a Carnival ball there!)

My Services for Olympic Travel

Because Olympic planning requires daily monitoring, insider connections, and rapid responses, I work with a special fee structure for these trips:

• $300/day per couple (based on trip length)
• +30% special event fee (to cover the extra oversight and coordination required)

This fee structure ensures I can stay in sync with shifting hotel minimums, ticket releases, and the moving pieces that make the Olympics both thrilling and complex.

Final Word

I couldn’t be more excited for these games. The historic city of Turin hosted them back in 2006. And before that, Cortina d’Ampezzo hosted the 1956 Winter Olympics. Italy has also hosted the Summer Olympics once: Rome in 1960.

The Milan–Cortina 2026 Games promise the best of both worlds: the elegance of Milan, the drama of the Dolomites, and a global stage set in Italy’s most cinematic landscapes. Trust me, the scenery will make your jaw drop.

Whether you’re courtside for figure skating, at the top of the Alpine runs, or savoring the closing ceremony in Verona, this is a once-in-a-lifetime experience — and it requires a deft hand to navigate.

When you’re ready, let’s talk through your must-have events and the right strategy for your Olympic journey.