Friends Turn March Madness Into a Decade-Long Tradition

Sometimes the best traditions start with a simple "why not?"

For Evan Romano and his kindergarten friend, that spontaneous question in 2017 launched what would become their favorite annual tradition. After Evan returned from a work trip to Las Vegas with positive reviews, they decided to make it a guys' trip during the first weekend of March Madness.

Their first stay was unforgettable for all the wrong reasons. The budget hotel room featured peeling stucco ceilings, sticky comforters, and questionable carpets that looked straight out of an 80s action movie. But the accommodations didn't matter because they spent their time exploring the Strip with beers in hand and experiencing something novel: legal sports betting.

Walking into Caesars Palace and seeing 20 massive TVs showing every college basketball game simultaneously felt like stepping onto another planet. Evan knew instantly this would become a repeat experience.

The tradition has grown beautifully over the years. A third childhood friend joined the crew, making the annual trip feel even more real and permanent. Their activities expanded beyond basketball and In-N-Out Burger to include good restaurants, spa treatments, meditation classes, and cigar lounges.

The accommodations have upgraded too. Now in their 30s, the friends have swapped sketchy hotel rooms for high thread count sheets and lobbies serving $30 glasses of scotch.

Sunny's Take

The pandemic cancelled their 2020 trip, the one year Evan's Penn State team finally made the tournament. But the tradition survived, proving its staying power.

As the friends entered their 30s, life got complicated in all the expected ways. One moved back to New Jersey, careers evolved, and responsibilities multiplied. In-person hangouts became harder to coordinate.

Yet this annual Vegas tradition has pulled them closer together each year. The joy extends beyond the trip itself into planning flights, choosing in-flight movies, and debating how many In-N-Out visits they can justify (this year's answer: a modest two).

After nearly a decade, Evan admits he barely follows college basketball anymore. But that was never really the point.

The real magic happens when three kindergarten friends step away from their adult lives to walk the Vegas Strip together, watching basketball and keeping a bond alive that geography and time can't break.