“Who: Lorraine Chin, 44, a public health educator in NYC. I decided to live the dream as a single, free-spirited woman—with a solo trip to Italy.

Where: I visited eight cities in Italy: Rome, Assisi, Florence, Venice, Padua, Verona, Milan, and Como.

Why: I had traveled prior to Paris, Scotland, Madrid, England—but as a crazy kid studying abroad. I knew seven days in northern Italy sightseeing, shopping, and eating fine cuisine was just what the doctor ordered.

The village of Assisi—one of the stops on Lorraine Chin’s life-changing trip to Italy. (Photo: Xavier / Flickr)

How I Changed After: I was working on Riker’s Island at the time and when I came back all-of-a-sudden I had an OMG moment and my eyes were open: I’m working in a jail. I started questioning how similar and different I was from the inmates I was serving. Could I be one paycheck away from being homeless? One condom away from having HIV/AIDS? I don’t take anything for granted anymore—there’s bigger purpose, bigger reason to life. It prompted me to get my real estate license and also work as a paralegal for a time. To make my life full and open.

The Cost: I paid $1,800 for a bus tour that included the flight, hotel, and guide. I was daring enough to go alone, but not daring enough to travel by myself and backpack independently across Italy like in my more no-consequences study-abroad days. What I didn’t realize till I got there is that my tour group was actually a pilgrimage!

Piazza San Marco. (Photo: Javier / Flickr)

What I Loved: The people. Everybody on the trip was there for a different reason—to find a different solace or spiritual awakening. There was even a group of nuns. After I got over the “oh wow” moment of realizing I was part of a pilgrimage, that’s when the eye-opening began. To see what all the other ladies were experiencing, people from all walks of life, made this trip to Italy deeper than I could have imagined.