“You girls sure you want to stay here? You shouldn’t stay out past dark. Definitely don’t walk around this area at night.”

Marcia and I were quiet, not sure how to respond to the cab driver. This was our first trip overseas on our own. We were 23. 

“Why do you say that?” I finally asked.

“You know this is the red light district, right?” replied the cabbie, in his thick Italian accent.

“Oh …” we both said, looking at each other with a mix of surprise and dejection in our eyes. Our jet-lagged brains weren’t quick enough to think of alternatives during those wee hours of the morning, and our weary souls just wanted to hit the sack, instead of spending the next hour or so wandering in the rain for another place to stay. Our weariness got the better of us, and we decided to just check-in and accept that this was where we’d be staying the last three nights of our trip.

“We’ll be careful, thank you,” I said.

“We’ll be sure not to walk around at night,” chimed in Marcia.

Welcome to Milan, I thought to myself. 

I had been looking forward to this trip for months, ever since Marcia called me up one night and asked if I was open to going on this adventure with her. She needed a break from her graduate ocean mapping classes. And I needed to find inspiration to continue fueling my creativity at work.

I was living in North Carolina and writing 2-3 stories a day on deadline for a metro daily newspaper, my first full-time job out of college. I was juggling straight news stories with lifestyle/features stories. Needless to say, I was a ball of stress. Since that conversation with Marcia – in between my furious clacking on the keyboard – I would picture myself sitting in a piazza sipping my cappuccino, getting lost among the fountains of marble Gods, or tip-toeing through the hushed tones of Renaissance art galleries. 

The last trip I made to Italy with my parents and sister two years prior felt so rushed that I wanted a redo of it. It was a large group tour, and we had powered through 12 cities in 8 days, spanning both France and Italy. Much of our trip had been spent on a charter bus, and we had no time to take in the actual vibe of each place. 

This time, I wanted to experience just Italy, on my terms. My timeline, my itinerary. 

Seven days of Marcia and I traveling through Italy – taking in everything with all five senses – sounded glorious. We would hit three key cities: Rome, Florence, and Milan. On our late-night trip-planning calls, we would talk excitedly about immersing ourselves in all the beautiful architecture, art, and language. 

Four years earlier, Marcia and I had become fast friends while living on the same floor in co-ed dorms sophomore year of undergrad. We were both young, Asian women of minimal stature (as I like to call it), often confused for sisters. We didn’t always see eye-to-eye on things, but she was always kind, well-intentioned, and supportive.

So here we were, embarking on our first overseas trip with no “adults.” First, we needed to book our flights, followed by lodging. After those were secure, we could then book our tickets for the galleries, opera, and tours of ancient ruins.

Back then, aggregate websites, like Kayak or Expedia, weren’t that robust, and there was a lack of presence of travel review websites, like TripAdvisor and travel blogs. There just wasn’t a lot of information out there.

We were also newbies to traveling cheap. 

It was Marcia’s idea to book a private room in a hostel. It felt like a steal! But it didn’t occur to either of us to research the area it was located in. It just seemed so close to the city center and the price was right. If only Airbnb and the concept of Superhosts were around back then. 

Nowadays, I’m a seasoned traveler who does all her research, reads the reviews, and compares prices across all the different websites. 

I book Airbnbs often, now that I’m in my 30s (in my 20s, I was booking rooms in hostels). And I always filter the Airbnbs to only show those run by Superhosts, have 4 or more stars, and have a majority of raving reviews. I check that it’s located close enough to city center or to most of the things I want to see, and that I can get there quickly and easily by foot, public transportation, or by Uber/Lyft. I also filter my search for a hair dryer, air conditioning, heater, and coffee for guests. And I make sure they let me drop off my bags there if I arrive in town before the check-in time. If I’m staying for more than 3 nights, in order to pack light, I book the ones that have a washer and dryer in the unit. (I then pack my own detergent pods and dryer sheets to do my laundry there, so I don’t have to re-wear stinky clothes.)

If I’m booking a hotel, I make sure it’s endorsed by TripAdvisor or at least has 4 or more stars on the TripAdvisor site, and that the location meets the same criteria I filter for when I search for Airbnbs. I make sure it’s a non-smoking room, has a hair dryer, and that there’s a free-cancellation period prior to my stay (should anything happen to change my plans). I also do my due diligence and compare prices on the reputable aggregate hotel booking sites, the direct hotel websites, and I also check my Chase Sapphire Reserve credit card booking portal for any discounts I can get there.

When I was in my 20s, I made sure the hostels I booked were in safe areas, were in walking distance or a short train ride from the city center, had free breakfast, allowed me to leave my bags there prior to check-in time, and had private rooms that could accommodate two people since I usually had a travel partner. Some people like the dorm-style rooms since they’re cheaper than the private rooms, and you get to make new friends with the people in your dorm  – but I just prefer my privacy.

Hostels tend to cater to young travelers between the ages of 16-25 and offer a great social scene, sometimes hosting mixers for their guests. When I booked hostels, I usually did it through trusted hostel sites, like Hostelworld or Hostelling International. I really enjoyed how easy it was to make conversation with strangers at the hostels, where we shared tips and advice for the area. We’d point each other to such things as yummy and affordable restaurants nearby, which company has the best zip lining experience, or strategies to optimize a visit to the local galleries and museums.

In the end, that hostel we found back in 2006 was antiquated, but it was clean, quiet, we had our private space, and we felt safe inside. We had to share the singular bathroom with others on the hall, but the bathroom door had a lock, it had hot running water, and it was kept clean.

That cabbie sure instilled some fear in us!

Nowadays, we can joke about that time we stayed in the red light district in Milan. And we wonder aloud if we would have known had the cab driver not tipped us off that first night? Then, we brush it off with a shared giggle and remind each other: Where’s the fun in traveling if you can’t look back later and laugh at all the blunders, run-ins, and mishaps you had along the way?

When I look back, not only did I learn the most from those moments where things had gone wrong, instead of perfectly, but I find that I also feel the most nostalgia for them.