
By Cassie Silkoff ’25
The Derby High School 2025 Italy trip planned for the duration of spring break has been in the works for quite some time now; notably since December of 2023. Italian teacher Hunter Sigona has tirelessly put together the perfect 10 day itinerary for the twelve students attending, himself, two other passengers, our chaperone, English Teacher Nicole Borges, and Paul McGuire, a parent and registered nurse.
Sigona began working on this trip with the hopes that his Italian students could utilize the skills they had learned in class and apply them in real time. When asked about the process of approval and steps taken, he explained, “We had to get the logistics ironed out first so that when we brought it to Mrs. Olson and the board, any questions they had we could answer them right off the bat.” Sigona also expressed his gratitude for the support Principal Jen.Olson has continuously shown him since the planning stage.
Exactly 50 days from Feb. 10, the fun will begin! The itinerary is jam-packed with a variety of cities to visit, landmarks to learn about, and culture to experience. The students will depart from Derby, Connecticut on April 10 and head to John F. Kennedy (JFK) Airport to catch a red-eye flight that will lay-over into Rome, the capital of Italy. After a few short hours there, they will take one more flight into Marco Polo Airport in Venice, Italy. On the first day in Venice, there will be a boat that takes everyone to the island of Murano where everyone will get a tour of the famous Glass Factory. On the second day, the students and chaperones will receive a tour of the city and experience a heavenly gondola ride. The crew will travel to Florence on the third day but stop in Pisa along the way where they will see beautiful landscapes such as The Leaning Tower of Pisa and some of the world’s most known cathedrals. The following day will also be spent in Florence where the group will view amazing historical sites like the Florence Bell Tower and more beautiful architecture of cathedrals and arch bridges. On the fifth day, the crew will take on Rome where they will stop in Siena to witness where important events such as horse races are held. “When in Rome,” they will explore the sculptures, paintings and then the Colosseum on the sixth day. The seventh day will be spent in the Vatican City where they will be given a tour of the Castle with an exclusive look at the dungeons. Afterwards, the group will be able to admire the beautiful fountains. Day 8, they will move on to Pompeii and tour the destruction that was caused by the eruption of Mt. Vesuvius, the volcano that froze the city in time with its molten lava and ash. They will spend the night there and the next day will finally depart from the Napolitano Airport in Napoli Italy into Rome and then from Rome on a direct flight back home, or at least to JFK and finally from JFK to DHS.
All that Sigona hopes for from this once-in-a-lifetime opportunity is “to give the students a worldly perspective,” and hopefully some more skills in the Italian language.

For many of the students, this is their first time leaving the country or even Connecticut at all. Sofia Rudus ‘26 exclaimed, “I’m not really nervous because I am going with a trusted group of people and I know everyone. I am actually really excited to see a new country and experience that with my friends. I am most excited about seeing the different cultures and being able to try real authentic Italian food.” The students are super excited and there is even a countdown where they reveal a new fact about Italy each day until the trip arrives, courtesy of Sigona’s sister, Gabriella Sigona.

As the trip approaches Sigona, Olson, and the other chaperones have worked diligently to ensure the safety and preparedness of everyone who is attending by making sure passports are secure, headcounts, currencies and medical emergencies have been planned for. When asked if he was excited or nervous, Sigona explained, “I am a little bit of it all. I am sure I will come out on the other end with a couple more gray hairs than I already have but I think it’s something that is worth all the stress and effort because going to Italy on a high school trip is not something that happens often.”
As the days tick down and the flight draws nearer, one thing is clear: this trip is about more than just checking off landmarks—it’s about creating memories, friendships, and building language skills that’ll last far longer than a gondola ride. Saying “arrivederci” to Derby High School for a week won’t be easy, but the students know they’ll come back with more than souvenirs—they’ll have stories to tell, photos to prove it, and maybe a few extra pounds from Italy’s finest gelato.
