We asked current boarding school students, as well as alumni, from Grand Cayman about their experience abroad. Find out what life is really like from the boarders themselves and how boarding school helps prepare students for future success.
Hayden
St. Michaels University School, CanadaHayden joined from CIS in Grade 9 and is currently in Grade 11.
What is the best thing about being at boarding school?
The new experiences and people you meet. Since coming to boarding school, I have met so many new people from all over the world and created unforgettable memories with them. These experiences are totally something I couldn’t imagine back home. From exploring downtown Victoria to seeing a sports game and everything in between, there are so many fun things to do.
What advice would you give a new boarding school student?
Get involved with as many of the school’s extracurriculars as soon as possible! This is a great way to explore all the different aspects of the school, such as sports teams or clubs/councils, and can help build friendships. As a boarder, you get lots of unique opportunities to be part of this community, and I think this naturally lets you meet lots of people.
What do you do on a weekend at boarding school?
Weekends are a time to relax and have a break from school. Typically I go downtown with friends, playing sports or going to the mall. I always make sure to set aside time to work out and study. Sometimes we also have scheduled activities like house games or outings for the boarding house.
How did you find the social side of boarding school when you first started?
For me, as more of a shy person, I wasn’t as open to going up to people and starting conversations as I should have been, looking back on it now. Luckily, there were so many amazing people who reached out to me and introduced themselves that I was okay and was able to establish a friend group. Sports and extracurriculars were the next step for me in meeting more people and building close bonds.
How does the workload compare to your previous school in Cayman?
The workload is significantly heavier here compared to Cayman, but it’s nothing I can’t handle. We also get 'prep time', which is a two-hour study period from Monday to Thursday. It’s a great opportunity and encourages me to do my school work.
Evan
Clongowes Wood College, IrelandEvan joined from CIS in 2nd year and is currently in 3rd year.
What is the best thing about being in a Boarding School?
There are many things, but my favourite is being able to live with my friends. In school, whether it’s in the dorms, in class, or out on the pitch, there is always something happening with the boys. In school, it’s very hard to be bored, as you can easily just ask friends to play sports or even just hang out. During the first few weeks of school, I didn’t know anyone, except the people I met on the first day. After another few weeks, I easily became friends with many people in the year. When you are in boarding school, you also get to know people much better, which allows everyone to connect on at least something. This also brought me and my friends much closer than we would have been if we were in a day school.
What advice would you give a new boarding school student?
Play sports such as rugby even if you aren’t into it. When you play rugby you get to have fun while connecting with your teammates on a different level than you would in class or in the dorms and this really helps you find your friends. Secondly, don't be afraid to be yourself as most people will get on better with you if you just be yourself and don't pretend to be someone just because you want to look good in front of certain people.
What is the hardest thing about being in a boarding school?
The hardest thing is not being able to go back home after school and the fact that home is so far away. When you come to a boarding school you will have to accept that you will basically get very little free time during the day. In school we are always doing something whether it's class, playing sports, or other activities—we’re always busy.
How did you find the social side of boarding school when you first started?
When I first started school in Clongowes it took some time to make all the friends I have now. Once you give it time and put yourself out there, you will make friends. I am in my second year and have made many friends and continue to make new friends and memories. The school also helps you when meeting new people but it's mostly up to you.
Konnor
Appleby College, CanadaKonnor joined from Cayman Prep in 2024 and is currently in Grade 9.
What is the best thing about being at boarding school?
The best thing about being in boarding school is getting to hang out with friends all the time and getting to go out on trips on the weekends.
What advice would you give a new boarding school student?
Try things you haven't done before and do not be afraid to meet new people.
What do you do on a weekend at boarding school?
Normally I leave the school to go to my relative's house on the weekends. However when I do stay, I sign up for all the boarder outings such as going to sports games, or driving go karts!
Did you experience homesickness? How did you overcome it?
I didn't really feel homesick because you are so busy at school that by the time you even think about it, you're back in Cayman on March break or Christmas break.
What are your favourite extracurricular activities?
I have done flag football, swimming and rugby. Every season is a different sport and you can choose from the options available for those seasons. Even if you don't know how to play a sport, there is normally an informative course for the sport, as well as a competitive version.
How does the workload compare to your previous school in Cayman?
The workload is a lot more and the school does have higher expectations. However this may be because in their grading system I was in middle school when I came to Appleby, so it might have just been because of the jump up to high school.
What does a school day look like for you?
My normal school day only has four lessons. However, they are all an hour and thirty minutes, instead of having six lessons that are just one hour. Appleby also has something called 'blue time' which falls after first period. Blue time changes depending on what day it is, but could be time for assembly, chapel or something else.
How did you find the social side of boarding school when you first started?
It felt a bit different because of the different cultures and people, but you become used to it quickly
Were there any subjects you didn’t feel adequately prepared for? And how did you overcome this?
I felt prepared for all my classes. However you must stay on top of your work or else it builds up!
Kyle
Appleby College, CanadaKyle is an Appleby College Alumni. He graduated in 1992.
How did your boarding school experience shape your path to university?
Living away from home at Appleby College made the transition to university very easy. I was comfortable managing my own schedule, living independently and making new friends.
What skills or values did you learn at boarding school that have proven most useful in adult life?
Firstly, respect for others’ space and perspectives. Sharing a dorm teaches diplomacy fast. Second, work ethic and time management. Evening study hall instilled a finish-it-before-fun habit I still rely on. And thirdly, resilience and self-belief. Appleby College pushed my boundaries—academically, athletically and socially—and showed me I could handle much more than I thought.
What piece of advice would you give parents who are considering boarding school for their child?
Although my own boarding school years were very positive and I knew what a beneficial impact it could have, having our son leave home was still extremely hard. Involving him from the start made a big difference—he genuinely wanted the challenge. Because the decision was his, it became an early test of independence, and I’ve seen his confidence grow as he proves to himself, he can manage on his own. It’s never easy to be apart, but I’m immensely proud of his willingness to embrace new challenges. My advice: make the decision together, then let your child take the lead.
What would you suggest a parent look for or avoid when choosing a boarding school?
Focus on community. I can’t speak for every school, but at Appleby College the same spirit I knew years ago is still evident today—modernised in the details, unchanged in its core values. I had no hesitation sending my son because, beyond my own memories, every Appleby graduate I’ve met over the past thirty years has been a genuinely impressive person. Look for a school where that kind of community endures.
Why would you recommend a child go to boarding school?
Boarding school broadens a child’s horizons. Living away from home accelerates independence in a structured, supportive setting; managing laundry, deadlines and relationships without a daily safety net rapidly builds self-reliance. Schools abroad also offer programmes Cayman can’t provide—whether that’s sports like skiing, specialised courses, or outdoor expeditions in the Canadian wilderness. Exposure to these experiences lets students pursue opportunities unavailable at home and gives them a taste of a wider world before they head to university.
