There’s something undeniably thrilling about letting go of control while traveling. Sure, planning can be great—meticulously researched itineraries, restaurant reservations made weeks in advance, and a perfectly curated list of must-see sights. But what if, instead of meticulously planning a trip, you left every decision to a single coin toss?

This is exactly what we set out to do on our latest adventure. The rules were simple: every major decision—where to go, what to eat, what activity to do—would be determined by flipping a coin. Heads, we go left; tails, we go right. Heads, we take the train; tails, we rent a bike. With nothing but a pocketful of loose change and a sense of adventure, we set out to see where fate (and a small metal disc) would take us.

Step One: Picking the Destination by Chance

Most people choose a destination based on careful thought—climate, cost, or personal interest. We did none of that. Instead, we pulled up a list of countries and assigned numbers to them. A roll of the dice determined Italy. From there, we flipped a coin: heads for Rome, tails for Milan. Milan it was. Our fate was sealed before we could even process it.

The idea of leaving an entire international trip to chance may sound absurd, but there was something liberating about knowing that we weren’t in charge. We were going where the universe (or at least a lucky coin) wanted us to go.

The Arrival: The First Decisions Begin

Stepping off the plane at Milan Malpensa, we realized just how much control we were relinquishing. Our first decision? How to get from the airport to the city. Heads for the train, tails for a taxi. The coin landed on heads, so off to the train station we went—no debating, no hesitation.

We arrived in Milan’s central station without a hotel reservation, because, of course, the next coin flip would decide where we stayed.

• Heads: A budget hostel

• Tails: A last-minute luxury hotel splurge

Tails. Fate apparently wanted us to experience the finer things in life, and after a quick search, we ended up in a surprisingly lavish hotel near the Duomo. Maybe the coin was onto something.

Where to Go First? Exploring by Coin Flip

Milan is filled with incredible things to see—the stunning Duomo di Milano, Leonardo da Vinci’s The Last Supper, the fashion district, charming canals, and countless museums. But instead of following a traditional itinerary, we let the coin dictate where we went.

• Heads: Visit the Duomo and climb to the rooftop.

• Tails: Walk aimlessly and see what we stumble upon.

Heads. Up the 251-step climb we went to the rooftop of Milan’s stunning Gothic cathedral. The view stretched across the city, and from up there, it felt like the whole world was ours to explore—one coin flip at a time.

For lunch, we flipped a coin again.

• Heads: A traditional Italian trattoria.

• Tails: Street food from a random vendor.

Tails. We ended up grabbing panzerotti, deep-fried stuffed pastries that are basically Italy’s answer to a gourmet Hot Pocket. Not our original plan, but delicious nonetheless.

Unexpected Detours and Surprises

Not every coin flip led to the best choice. At one point, we found ourselves at a crossroads near Parco Sempione, with two options:

• Heads: Rent a bike and explore the park.

• Tails: Hop on the first tram we see without knowing where it goes.

Tails. Five minutes later, we were crammed into a tram heading in the wrong direction, completely lost. The driver announced the final stop, and we found ourselves in a quiet Milanese neighborhood far from any tourist attractions.

At first, we were tempted to break the rules and check Google Maps, but we stuck to the plan. We wandered the streets, eventually finding a tiny café where no one spoke English. We ordered whatever the waiter recommended, which turned out to be sbrisolona, a crunchy almond cake that became our new favorite Italian dessert.

Would we have found this place otherwise? Probably not. But that was the beauty of the coin flip challenge—embracing the unexpected.

When Things Got a Little…Chaotic

Not all decisions were as charming as our accidental café discovery. Some put us in less-than-ideal situations.

• Heads: Take a leisurely train ride to Lake Como for a scenic afternoon.

• Tails: Rent a Vespa and drive without GPS.

Tails. It took exactly 12 minutes of navigating Milanese traffic for us to regret this choice. Dodging aggressive Italian drivers and weaving through roundabouts, we realized the coin was not concerned with our safety. Eventually, we got the hang of it and made our way toward Monza, where we accidentally ended up at the famous Monza Circuit, home to Formula 1 racing. Was it part of the plan? No. Did it end up being one of the coolest things we stumbled upon? Absolutely.

Pushing the Limits: Letting the Coin Decide Our Fate for a Full Day

By the end of the trip, we wanted to take the challenge to the extreme—letting the coin decide every decision for one full day.

• Breakfast:

• Heads: Espresso and a cornetto.

• Tails: Whatever the next person in line orders.

• Result: Tails. We ended up with brioche con gelato—basically, an ice cream sandwich for breakfast. No regrets.

• Morning Activity:

• Heads: Visit a museum.

• Tails: Take a train to a random town.

• Result: Tails. We boarded a train to Pavia, a historic town we had never heard of but quickly fell in love with.

• Lunch:

• Heads: Pizza.

• Tails: Something we can’t pronounce.

• Result: Tails. We ended up with casoncelli, stuffed pasta from Lombardy, which was way better than our usual pizza order.

• Final Decision of the Trip:

• Heads: Extend the challenge for another day in a new city.

• Tails: Head to the airport as planned.

• Result: Heads.

That’s right—the coin wasn’t done with us yet. Instead of flying home, we booked a last-minute train to Florence, where the game would continue for another day.

What We Learned from the Coin Flip Challenge

By the end of our journey, we realized something profound: travel is best when it’s unpredictable.

• It forced us out of our comfort zones.

• It took us to places we never would have planned.

• It made us realize that sometimes, the best experiences happen when you surrender control.

While not every flip worked in our favor (looking at you, Vespa ride through Milan traffic), the adventure was unforgettable. We found new favorite foods, met fascinating people, and uncovered hidden gems—all because of a simple coin toss.

Would we do it again? Absolutely. Maybe next time, we’ll take it even further—perhaps flipping a coin to decide which continent to visit next.

Because sometimes, the best way to travel is to let fate decide.