Chasing the Olympics: What We Learned About Milano Cortina 2026 and What You Need to Know for LA 2028

Episode 18 of Marrying Your Passions: The DINK Travel and Adventure Podcast

Bryan and his family at the Olympic rings!

If you have ever watched the Olympics from your couch and thought, what would it actually take to be there, this one is for you. We sat down with author and event traveler Bryan Michael, and he answered that question in a way that honestly changed how we think about bucket list travel.

Bryan and his wife Shannan and their son Deacon attended the Milano Cortina 2026 Winter Olympics this past February. He came back with stories, hard-won logistics advice, and a perspective on the Games that goes deeper than just the sports. And because we have already entered the LA 2028 lottery, we had about a million questions.

Here is what we learned.

It Takes Years, Not Months

One of the first things Bryan told us is that a trip to the Olympics is not something you plan six months out. He started planning Milano Cortina two years in advance and still felt like he was scrambling at times. The lottery system opens during the previous Olympics, not the previous Winter Olympics, so the window is longer than most people realize. If LA 2028 is on your radar, the time to start paying attention is now.

The beautiful town of Livigno, Italy where the Richards took in many Olympic events.

The Lottery Is Just the Beginning

Getting into the lottery is step one but it does not guarantee you the events you want. Bryan was lucky enough to land in group one of the Milano Cortina lottery and still could not get tickets to some of the events he had his eye on. The downhill events were largely unavailable early on, likely snapped up by hospitality packages, and some were only released later when he had already committed to a different itinerary.

His advice is to enter the lottery as early as possible, have a clear idea of which events matter most to you, and build some flexibility into your plan so you can pivot when tickets become available unexpectedly. The ticket exchange app also opens during the Games themselves, which means opportunities come up even after you arrive.

A mogul skier coming down the slope!

The Zones Matter More Than You Think

This was one of the biggest surprises for us listening to Bryan talk through his experience. The Milano Cortina Games were spread across six different cities, not just two, and getting between them was a serious logistical challenge. Some people Bryan met had no idea how spread out everything was and ended up catching cabs at three in the morning or hiring private cars for five-hour drives through the Alps.

Bryan split his trip between Milan and Livigno and said he would have skipped Milan almost entirely if he were doing it again. For LA 2028, the Games will also be spread across zones and potentially across the country for some sports. Bryan's advice is to pick your zone, stick to it, and consider moving accommodations mid-trip rather than trying to chase events across a wide geography.

Bryan and his family at the semi-final women's hockey game between Canada and Switzerland.

Book Your Accommodations the Moment They Become Available

This was Bryan's biggest regret and probably the most actionable advice in the whole conversation. He and Shannan waited too long to book and found themselves scrambling for options that were either unavailable or significantly more expensive than they would have been earlier. In Livigno, a small mountain town with very limited lodging, they ended up paying 800 euros a night for a bare bones one-bedroom Airbnb.

Was it worth it? Bryan says yes because being able to walk to every event made the whole trip easier. But the price was driven up entirely by waiting. His advice is to check weekly from the moment the Games are announced to see when accommodations become bookable. Do not wait until it feels urgent because by then it already is.

The Livigno region's food has a strong German influence including pizza with french fries!

What to Pack and What to Leave Behind

Security was inconsistent across venues at Milano Cortina and that caught a lot of people off guard. Some venues were relaxed and others were confiscating cowbells, power banks, and water bottle lids. Bryan's rule of thumb is simple. If it has sentimental value, leave it at home. He smuggled in his Snoop Dogg cowbell at one venue and wisely left it behind at the hockey game. A man standing next to him had a cowbell he had carried to four Olympics with stickers from every Games on it and watched it get taken away at the door.

Beyond that, layers are essential for outdoor winter events, card games are surprisingly useful for long waits and downtime, and pre-booking restaurant reservations matters more than you think. In the Livigno area, restaurants closed from around 4:30 to 7:30 in the evening, which caught them off guard on their first night.

The Olympic rings carved in ice in Lavigno.

The Experience Is Unlike Anything Else

We asked Bryan to describe the moment he walked into his first Olympic venue and what he said stuck with us. From the time the gates opened two hours before the event, the organizers were working the crowd with face painting, dance competitions, mascots, and games. By the time the first athlete dropped into the course, the energy was already electric.

Women's moguls

His most memorable moment came during the women's moguls event when the United States took gold and silver. Elizabeth Lindley, who did not have the same fanfare as some of her teammates, won the gold. And standing there singing the national anthem while people from other countries stopped to take photos and videos of the Americans, Bryan said that was exactly the Olympic experience he had been dreaming about since watching the Lillehammer Games as a kid.

What struck us most listening to him talk about it was not just the sports. It was the people. He talked about meeting fans from Austria, Czechoslovakia, and Seattle, and a group who had attended six Olympics together. He talked about how there was none of the animosity that dominates so much of the news right now. Just people from everywhere cheering for the same athletes coming down a mountain. That alone sounds worth the trip.

Bryan enjoying a cold one at the moguls!

Going All In on Your Passion

Bryan is not just an event traveler. He is also a crime thriller author who this year walked away from a steady career to pursue fiction writing full time. His debut novel Blood Debt is out now and his second book Past Due drops this month.

Bryan realizing that he is a published author as he sees his book, Blood Debt for the first time!

What we loved about this part of the conversation is how honest Bryan was about what the grind actually looks like. He had finished novels sitting on his hard drive for years before he finally decided to treat writing like the business he was trained to run, applying his MBA in Marketing from the University of Miami directly to cover design, editorial positioning, Amazon category research, and distribution. He self-published under the name Bryan Michael and founded his own independent publishing company, Skillet Press.

He talked about how book sales went nowhere at first because he was not out there marketing. He talked about spending eight hours getting his book uploaded to IngramSpark. He talked about reaching out to every book club that meets at a brewery he could find. And he talked about why he finally made the leap to writing full time, because he did not want to be sitting in a nursing home someday asking himself what if.

Check out Blood Debt for a fast paced crime thriller!

That hits close to home for us. We started this podcast and there were long stretches where we wondered if we should keep going. Bryan's story is a good reminder that the grind is part of it and that the people who make it are the ones who keep showing up.

Listen to the Full Episode

Bryan covered so much more in our conversation including the full breakdown of the ticketing process, his thoughts on what makes attending a live sporting event worth it versus watching from home, and some genuinely funny stories about Airbnb anxiety and Olympic security. You do not want to miss it.

You can find Blood Debt and the upcoming Past Due at bryanmichaelauthor.com or on Amazon. Autographed copies and book club discounts are available directly on his website. Follow Bryan at @bryanmichaelauthor on Instagram and Facebook.

And if you are thinking about LA 2028 Olympics, start paying attention now. Bryan gave us a head start and we are passing it along to you.

Bryan and his family at the moguls.

Places Mentioned in This Episode

Olympics

Places visited by Bryan and his family

Bryan's Links

Our Links

Bryan enjoying one of the Corona activations.

Bryan enjoying his Coach Snoop cowbell!

Shannan also enjoyed the activations too!

Bryan signing a copy of Blood Debt!

Spaetzle and pulled pork at a local brewery in Livigno.

Bryan and his family at the Milan Cathedral.

The Arc of Peace in Milan.

Marrying Your Passions is hosted by Nathan and Alicia Adams, a married DINK couple (Dual Income, No Kids) who travel, run marathons, scuba dive, and eat their way through life together. Whether you are a DINK couple, empty nester, or anyone ready to adventure NOW, this podcast is for you. New episodes every other week. Subscribe, leave us a review, and keep adventuring!

Alicia, Peppermint Patty, and Nathan enjoying a night outside next to the canal in their backyard!

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