A Band of Traveling Friends: The Sao Miguel Story

In friends, Friendships, Portugal, Travel by Katelyn9 Comments

When I stepped onto the tarmac at the Ponta Delgada airport I was half asleep. My hair was whipping around my face due to the wind and I could smell the salty scent of the ocean. I was here. I had a knot in my stomach; partly because the bumpy plane ride to the island stirred up my motion sickness and partly because this was my first real solo trip. For the first time in a foreign country, I was traveling alone. I wasn’t meeting up with a friend or a group. I was alone on a small island in the middle of the Atlantic Ocean not able to speak a word of Portuguese.

jellyfishquoteLooking around the passport line I tried to find similar travelers. Perhaps I would meet a new friend. Perhaps we would all just disembark our plane and disperse across the tiny island. There was an interesting mix of travelers. Some were locals returning home happily chatting away with their family members while waiting for that official stamp that determines that they are home. Others were traveling with friends and family members. Some with small children, others with elderly family members. I couldn’t see many that were around my age. Finally I made it to the man that had the power to accept me or deny me. I handed him my passport. He looked me up and down and I heard the telltale “smack” of the stamp and my passport was handed back to me with a nod.

I took a beeline to the bus ticket counter and purchased my ticket to the airport shuttle bus. Once on the bus, it was myself, a young couple, and another solo female traveler. I gave her a smile and she looked away. No bueno.

I’m a naturally shy and quiet person. As a child I was extremely shy. You could have said “boo” to me and I would have ran to hide behind my mother’s legs. At every single parent-teacher conference growing up, my teachers would always say the same thing, “Katelyn is a standout student, but she needs to talk more.” The same thing year after to year like a broken record. Chalk it up to low confidence or low self-esteem or whatever psychological mumble-jumble that you want to classify me as, but I’ve always been a more of an introvert. Being an introvert has its benefits, like being able to sit back and make observations about the world around me. However, at times it can be hard to put myself out to make friends, especially now as an adult.

Everyone travels for their own reasons. Maybe it is to see the beauty of the world through nature. Perhaps it is to relax on a beach and drink Pina coladas all day. Or maybe it is to get more stamps in one’s passport. There is no right or wrong way to travel. You’ll often find this debate on travel blogs or at the dinner table at hostels, but my belief is everyone travels for their own reasons. I travel to get outside my comfort zone. A lot of people enjoy living their lives doing the same thing day after day. If that’s your thing then that’s totally cool with me. I just can’t live my life that way. Life is short and you never know when it might end; there is so much in this world that I want to see and experience. I want to see the beauty and awe of the Northern Lights. I want to feel my heart beat rapidly as a herd of bulls run towards me over century’s old cobblestone streets in Pamplona. I want to experience the tears of joy and pain of reaching the top of Kilimanjaro and looking over the roof of Africa to see the sprawling, un-touched African plateau. I want to sit on a beach in South East Asia and witness a world-famous sunset next to someone I care deeply about while smelling the sweet smell of saltwater and drinking a cold beer. Most of all, I just want to live outside my comfort zone and become the best person that I can become.

I was nervous about this trip because I wasn’t sure if I would make friends at my hostel. The second the front desk girl at the hostel introduced me to my new roommates and suggested I hop in their car with them, I knew we were going to be “family.” And our little family continued to grow over the coming days to something special. Sao Miguel is an absolutely stunning island full of beauty, mystery, and friendly locals. You’ll hear those stories in the coming weeks, but I wanted to share with you my most favorite part of my trip – the people that became my family.

Travel friends really aren’t that hard to make in hostels. Generally we’re all there to experience the city, the country, the world. Wanderlust can cause many unlikely travelers to bond instantly and become the best of friends over night. Usually after a few beers. I’ve made lots of friends from my travels in hostels and my travel groups. I may be naturally an introvert, but when I’m traveling I push myself outside my comfort zone and play more of an extrovert. However, those travel friends are now just more Facebook friends that I keep in contact with occasionally. But these people I met in Sao Miguel are actually people that I would hang out with in the “real world.”

I’m going to attempt to introduce you this wonderful, crazy cast of characters that entered my life in Ponta Delgada. Without them, my trip would have been boring and that is an understatement. I don’t think my travel mates realized that throughout our adventures I was observing not only the beautiful landscape of Sao Miguel, but also their impressions and reactions to all our conversations and experiences. As someone who is a trained scientist, I tend to observe and then ask 5000 questions afterwards because I am genuinely interested in what makes people tick. I think the poor Teacher and Brown Student got the grunt of my questions, but you’ll meet them a little later. But first, here is the story of a girl and her adopted family (just so you know, as I write this I’m singing the Brady Bunch theme song in my head)…

The initial group from the Vintage Place Guesthouse and the Brown Student

The initial group from the Vintage Place Guesthouse and the Brown Student

The first characters I met in the entry way of the Vintage Place Guesthouse in Ponta Delgada were the Artist and the Scholar. The Artist is 25 years old and lives in Montreal. I didn’t realize it until I saw her Instagram account, but she is a very talented painter. The Scholar is 24 years old and also from Montreal. They came on this trip together and often bickered like sisters in French. I have dubbed her the Scholar because throughout our week’s adventures we would have conversations and debates about random things, like school uniforms, immigration, and food; she would always have a strong intellectual argument for her side of the debate. She is a bit more reserved than the Artist, but I was always impressed with her logic and intelligence and that is something that I highly respect in a person. Both girls speak multiple languages as they emigrated from Uzbekistan as children to Canada with their families. I was always thrilled when they would entertain my questions about the former Soviet Union and what it was like to grow up there and then move a world away to Canada.

The next two characters in our initial family were the two boys – the Fashionable Filipino and the Baby. The Fashionable Filipino is a total sweetheart. He is a soft-spoken, well-dressed man from Toronto. He originally came from the Philippines and lived in Providence, RI for a few years before moving to Toronto and officially becoming a Canadian citizen. He spent many years as an accountant, a bad one he told me, but I doubt that. During our time in Sao Miguel he found out he passed the national test to become an immigration specialist to help immigrants become Canadian citizens. When he talks about the test and his new career path, you can tell it is something that he is genuinely passionate about and I’m excited that he is able to follow his passions in life. He is someone that will truly fight tooth and nail to get you the paperwork you need to move to Canada. The Baby has been dubbed the Baby because he was the youngest at 18 years old. He just finished high school this past year making me feel old as I approach my 10 year reunion this coming year. Gulp! He hails from outside of Toronto and had been in Ponta Delgada for almost two weeks when I arrived. This was his first solo trip, but has traveled extensively throughout Europe with his family. A small part of me was a little jealous of that. I wish my parents prioritized traveling with my sisters and me. I know that if I am lucky enough to have a family of my own in the future, we will be a traveling family.

The Baby was probably the tallest of the group and has an innate curiosity in the world, much like myself (minus the tall part). I could see the wanderlust in his eyes and his eagerness to see the world. Go for it young grasshopper! The Baby only traveled a couple of days with us before he left for a WOOFing experience for a week. But he soon returned a day later when his host was less than hospitable. We, of course, welcomed him back with open arms.

Our group of 5 traveled together crammed into a tiny little European car for a couple of days before we adopted a couple new members. On Thanksgiving, I and all my new Canadian friends celebrated Thanksgiving with a spaghetti dinner at the hostel cooked by the Fashionable Filipino who is an excellent cook. Personally, I’m not actually a fan of spaghetti but while traveling I always eat the food I am offered, especially if it’s made with love. The spaghetti was delicious though! The Fashionable Filipino had been in contact with a couple of guys from the US through Couchsurfing. One of them, the Brown Student, came to dinner that night and succeed to be adopted into our little hostel family with open arms.

The Brown Student was staying nearby in another hostel all by himself. Seriously, he had the entire hostel to himself. He is, as his name implies, a senior at Brown University in Providence, RI with a double major in Computer Science and Economics. He’s a bit of a smarty pants, which came in handy at times. He is in the US on a student visa from Beijing, China. He has lived in several places around the world and speaks impeccable English, which I was later told he learned through watching Friends and Lost. The Brown Student is a total sweetheart and acts much older than his 22 years. He was certainly a great addition to our little family. Now, the Brown Student arrived on the same plane as I did with the Teacher, who the Brown Student had connected with via Couchsurfing prior to liftoff, but I don’t recall seeing either of them on the plane. That night after our spaghetti dinner, we headed out to the local bar for some drinks and colorful conversations about education, immigration and make-up. The Fashionable Filipino and I made plans to explore more of the island with the Brown Student and the enigmatic Teacher.


Our adventures started a bit later than we would have liked because the Teacher was either a very late sleeper or out exploring and getting into trouble on his own. As someone who is very Type A and has to be constantly on-the-go all the time, it was a bit frustrating. The Fashionable Filipino was a bit funnier about the situation threating to not talk to him. As we waited and waited, we crafted a storyline that the Fashionable Filipino was mute and could not talk to the Teacher. But that lasted all of 0.002 seconds when we walked out the door to get into the car.

Out of all the people in our group, I think I connected the best with the Teacher. We are of similar age and shared interests and he surprisingly put up with my annoying questions about the education system. He is also the only other person I’ve ever met not to like California wine too. Now I can tell people it’s not just me when they look at me with two heads when they try to serve me that crap! The Teacher is an interesting fellow for multiple reasons. First, he has two different colored eyes; a blue and a brown. I find that both mesmerizing and frightening at the same time. Secondly, he claims to be a history teacher from western Massachusetts, but I’m convinced that he’s really a spy. He has a Master’s degree in Middle East studies from a university in Israel and has traveled extensively throughout northern Africa and Europe. He once confidently stated that he can’t be beat in trivia, but I think I could give him a run for his money. This was his second trip to the Azores as the previous year he came for the holiday with his mum. How sweet. A typical Irish Catholic momma’s boy. And he only tried to kill us once by driving in the wrong lane into oncoming traffic on the highway. He claims that he was trying to pass a car, but I’m not sure I can trust a guy with two different colored eyes.

The last edition to our little travel family occurred that night when we got back to the hostel. We had a new roommate, a guy I recognized from the plane because he sat in front of me. I remember him because of his haircut, it was similar to the men in Peaky Blinders. Because I mentioned Peaky Blinders I must now go down this tangent. Since our flight was delayed for a few hours due to mechanical issues, I had time to kill. I just started watching Peaky Blinders on Netflix the weekend before and pretty much binged watched it that week. I had a few episodes left so I downloaded the app on my phone and watched a couple of episodes in the airport. I got halfway through the last episode of season 2 before I got bored and started pacing the terminal. Now I don’t usually like the bad boys, but I’ll take Tommy Shelby any day! Those baby blue eyes! Swoon. Now, let’s get back to the real story.

Enter the Soccer Coach. He is in his early 30s from Cape Cod. He is a complete soccer fanatic and spends his falls coaching youth soccer. He is a big music fan and every time the local band at the bar played a song I didn’t recognize I would turn to him. He is of Irish and French Canadian heritage and part of his family hails from Downeast Maine. We could possibly be cousins as my entire family is French Canadian, but I doubt it. I’m also pretty sure one of my coworkers is my cousin too. The Soccer Coach has traveled to Iceland, where I’m heading in October, so we bonded over his love of Iceland and everything Viking. I think much of that night at the bar our group discussed Montreal, poutine, the difference between college in Canada and the US, and everything Viking. After a few beers, everything goes.

There are a few other characters that joined us on our last night together, such as the young film maker from Boston who is originally from Brazil and the cute 19-year old local girl that the boys quickly turned on their inner Casanova for. You’ll hear more about them in later stories. As any good storyteller will do, they first must introduce you to the main characters of the story. Some characters you may dislike, others you may love. I was very lucky in my story to meet a colorful cast of characters that truly made my trip the awesome experience it was. We discussed many of times having a reunion as we are all located in the New England/Montreal/Toronto area making travel realistic. I truly hope that we can all meet again and can continue our stories. And I also hope, that if we meet again, that you don’t kill me in my sleep after reading this! 🙂

So this one is for you, my Ponta Delgada family. It is a true pleasure to meet every one of you and experience such a beautiful place in the world. We bonded over our mutual love of poutine and travel and I am grateful to call you all friends no matter where you live in the world. And thanks for putting up with my quirks and need to ask an excessive amount of probing questions. Cheers!


Have you made any special traveling friends? Do you still keep in contact with them?



  1. Like you, I’m more of an introvert. Yet for some reason, whenever I travel solo, that’s when the extrovert comes out and I love getting to meet and interact with new people. Not sure if it’s because I’m in an unfamiliar setting or the true sense of adventure just pops out, but whatever the reason, I’m finally learning to embrace it a bit more in my “normal” life back home!

    1. Author

      Thanks Beth! I think as every year I get older, I become a bit more of an extrovert. But perhaps that because I stopped caring about what people think of me too! 🙂

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  7. Hi Katelyn,

    Thanks for sharing your story! I’m an university student going on exchange in January and just like you, I’m planning on starting my exchange off with a bit of solo travelling to Sao Miguel. I was just wondering if you could give me some tips for travelling alone there on a budget. I’m not sure if I’ll be as fortunate as you and meet some great people to explore the island with!

    Would love to hear back if you have time, thank you!!

    1. Author

      Hi Sam! Enjoy your exchange experience! Where are you heading? I think you’ll like Sao Miguel. Sign up for Couchsurfing. You don’t actually have to do couchsurfing if you’re uncomfortable with it, but you can post a message with your travel dates and you meet might other travelers that way. That’s how I met a few of the people I met during my stay. The locals are really friendly and most speak very good English too so don’t be afraid to talk to them. There’s a university right in town so you’ll find similar aged people as yourself. There is a bus that runs around the island. You’ll have to check the schedule, but it might be a good way to get around. I found food and drinks to be quite cheap and there are several groceries you can purchase food from and then cook. I stayed at The Vintage Place, which I highly recommend and there are several other hostels in town, too. Good luck and enjoy your travels! 🙂

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