A Rising College Freshman's Tips on Travel Planning

By: Siahra Castillo, A Daytripper Ambassador - Princeton Class of 2023


Siahra Castillo, one of our Daytripper Ambassadors, is a self-described travel junkie and a girl after our own hearts. Here she discusses the excitement of planning her families trips and tours and the serendipity of unexpected discoveries. We hope she inspires you and your kids to plan your college tours together and turn it from a chore into a memorable bonding experience.

As a self-diagnosed control freak, I have always jumped at the chance of helping my parents plan family vacations, day trips, or weekend excursions. The Notes app on my phone is filled with itineraries for days in New York City, where my sister and I often spent much of the summer. When I learn that a trip is coming up, I leap to the Internet and scour Pinterest, TripAdvisor, and Yelp to find the perfect hotels, restaurants, and other attractions. By the time we are packing our suitcases, it is almost like I have already been to our destination. My mind swirls with reviewers’ testaments, both good and bad. I have studied the particular area on Google Maps so rigorously that I feel as if I know the foreign streets like the back of my hand. Planning the trip is the most enjoyable part of the entire experience for me. All of this planning experience came in handy when I began the college process and was suddenly faced with multiple schools to visit, and day trips to plan.

The summer before Junior year we took a trip to California, traveling along the coast from San Diego to Los Angeles to Santa Monica. I was not looking on the West coast for schools, so we did not visit any. It was a more spontaneous vacation, one without a hard and fast plan. As much as I love to control everything, it was nice to let go and see where the trip took us. Still, I researched each city we stopped in, and I was able to make some generally well-received recommendations for my family. My favorites were hiking in Torrey Pines State Park, eating decked-out waffle pops from Sweet Comforts on our way to Santa Monica, and eating breakfast at the trendy food and vendor hotspot that is Grand Central Market in LA. It was inspiring to see all that California had to offer, and the trip had me ready to research for all the college touring I would be doing beginning in my Junior year. 

The prospect of traveling to a plethora of new places was exhilarating. I had only been to a handful of states before, so I knew I had a lot of unexplored territory ahead of me. One of the first trips my family and I took to gain information about a college was a weekend getaway to Washington D.C. The schools on our list were Georgetown University, George Washington University, and American University. I did the usual research on new and exciting things to try, signed up for information sessions and campus tours, and worked visits to the capital’s most iconic landmarks into the busy itinerary. After a full day of touring, I would propose a restaurant for dinner, and we would explore the city. One night we saw a modern interpretation of Hamlet, on another, we drove past Capitol Hill. When we were not touring, we spent our days visiting the White House, browsing the exhibits at the National Portrait Gallery, or enjoying a traditional southern brunch. 

At the end of the whole process, my search history is full of “Top 10” lists, and I am wistfully looking back on a great stay in a new place. The key, I have found, is balancing spontaneity with researched planning. Using Daytripper University’s touring itineraries has definitely helped in this regard. Now when I plan a trip, I can see hotel, dining, and entertainment recommendations organized by campus. This allows me to limit the time I spend researching while still fulfilling my need to perfect the plan, and gives me more room to have fun exploring a new location on my own. As much as I would love to plan a trip down to the minute, I would not want to sacrifice the genuine excitement I have when we discover something new as a family by just walking down a street. I love discovering hidden gems that do not come up when I research and adding them to my list for a future trip. I am pretty fortunate to have a family that allows me to commandeer much of our vacations, but occasionally I do not mind handing over the reins.