When I planned my first “big girl” trip in 2013, I had no idea what I was doing. I was a 20-year-old college student with a limited budget and a dream to revisit New York City to celebrate my 21st birthday.
I had been on a total of one trip without a parent or school chaperone, and that was to Disney World the summer before. I had never planned a trip before and I certainly didn’t remember the geography of a city I had been to once.I booked our flights and hotel for a total of $300 a person for four nights. There were three of us going: my sister, my best friend and me.
We were staying at a Howard Johnson in New Jersey close to the Newark airport. The daily travel via hotel shuttle to Newark and then Amtrak to Penn Station left us with limited time in the city. To this day, I’m not totally sure how we managed to make it to the Met, MoMA, the Statue of Liberty, Times Square, Central Park, the 9/11 Memorial and Rockefeller Center in those few days and practically no knowledge of the city.
We traversed one end of Manhattan to the other every day we were there. On top of this, we were close to freezing every day because we had woefully under packed for the cold weather of mid-November in Manhattan. By the last night, we were delirious. We probably got a combined 12 hours of sleep the whole trip.

When we landed in New Orleans three days later, I wanted to turn around and go right back. I left part of my soul in Manhattan on that trip. It’s been that way ever since, except I got much better at planning.
In December 2014, my sister and I went back to New York as a celebration of my college graduation. The experience was night and day from the 2012 trip. We booked our hotel and flights on BookIt.com for about $1,300. The hotel was close to the Flatiron District, a couple blocks from a subway stop and it had a doorman.
Each day was planned based on location. Uptown one day, midtown the next and downtown the last. We saved time and got more done, and we even managed to see a Broadway show. Since then, we’ve been back to New York several times as well as Boston, Baltimore and Seattle.
Planning has become easier with each trip, but I’m about to embark on the longest and most involved adventure yet: a tour of Italy.
Keep wandering friends.