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Going on Tour with My Grandma Was the Best Trip I've Ever Taken

Alex Shaked
by Alex Shaked

January 30, 2024

6 minute read

Going on tour is an incredible experience, but what makes it more incredible is the company you keep.

I’m a writer at Collette, and I just got back from my very first tour. Our Tropical Costa Rica tour was so special, but it was made more special because I had the best roommate ever: my grandmother Maria.

I loved learning about a different culture and a different part of the world from my own, but seeing it through her eyes and sharing that experience with her made this the most important trip of my life.

So. How did we land on this trip? Did we want to rip each other’s hair out by the end? Are we ready to take our intergenerational travel duo to another continent? Here’s the scoop:

The Road to Costa Rica

Over lunch one day, I told my grandmother that I would be heading to Morocco on a business trip. She shared with me that many, many years ago, her friend asked her to go to Morocco. Grandma couldn’t afford it at the time, and then her friend never asked her to go on a trip again. They’re still friends and my grandmother is still upset about it.

But the story prompted the obvious question: “Where are we going?”

She had a Collette brochure in her hands the next weekend. As families do, we immediately argued about who should pick the trip (her, obviously, but she wanted me to…). After the dust settled, we narrowed it down to three tours. I was unsurprised that the woman who loves flowers and has had pet birds for most of my life had picked the Tropical Costa Rica tour. We decided to go in January, because leaving New England in the winter for a tropical climate seemed like a good move.

Grandma and Granddaughter


My grandmother is 81 years old. People wondered if I was nervous and if she was active prior to our trip. The truth is, I wasn't worried a bit — my grandmother and I take walks together frequently and she's outpaced me on more than one occasion.

Instead of matching t-shirts, we got matching hiking boots for this trip. We decided to break them in on what she had labeled a short walk on a warm November afternoon. Per my pedometer, that short walk was 8,000 steps by the time we got home.

But she puts on a brave front; she didn’t reveal that she was a little anxious before we got on tour until the end of our trip. But what was heartwarming was that she didn’t share that with me: She was open and vulnerable with her peers on tour who had cheered her on.

The Tour Experience

My grandmother has several traits that make her the perfect traveller for Collette: She’s curious, she loves to meet new people, and her favourite phrase is “why not?” She is always willing to try something new and step outside of her comfort zone.

Needless to say, she was unfazed that the first significant snow of the season was due to make landfall the day of our departure. To avoid that we left a day early, which meant two pre-night stays instead of the one we had planned on.

An extra day by the pool sounded pretty good to me, but I could tell once she had figured out the lay of the land, seen what birds were hanging out at the hotel, and checked out all the trees and flowers on the grounds, she was bored and ready to go do something.

But the boredom didn’t last. Other people in our group started trickling in, and before we knew it, we were off.

I could tell you about how much fun we had learning how coffee was made, seeing how a local finca functions, and how cool the view was from the cloud forest. And whilst the itinerary was great, the moments I'll never forget were the ones that couldn't have been planned alongside our fellow travellers on tour.

San Jose was the place where we met Bunny and her four adult daughters who were on an intergenerational tour journey of their own. We watched Bunny prep sugar cane to make juice, and we got to know her daughters a little more each day. Bunny’s daughter Nancy and I share a guilty pleasure: Taco Bell.

The farm was where my grandma and I sat down for lunch with Preston and Marcus, who had won the tour on Wheel of Fortune. They wanted to hear all about my grandmother’s upbringing in a small village in Portugal, what they could expect from a trip to her home country, and how much she loves Portuguese olive oil. Preston, we learned, was big on both olive oil and the fresh juice we had every day on tour. I always knew to go to him if I needed the scoop on the juice.

Arenal was the spot where we met Mary from Kansas. She told us about the 50+ program through her local parks and rec, shared stories with us about her son, and spoke about her family’s immigration to the U.S. from the Baltics. We shared meals with her often, and she offered me some really solid book recommendations.

Monteverde was the place I watched my grandmother, who had worked hard to stay active and mobile after what could have been a life-altering fall several years ago, climb her way up some steep and windy stairs to cross a hanging bridge in a cloud forest. It’s also the place where a shuttle driver whistled in just a way that it felt like my grandfather, who had always been either cracking a joke or whistling, was with us for a quick moment.

In Guanacaste, we caught a surprise poolside concert and hung out with Annette and Julie from Las Vegas by way of Chicago. We laughed about close critter encounters we’d all had, talked about our travel dreams, and celebrated the loved ones we had lost.

Everywhere we went, though, I was especially touched by how my grandmother was able to tie elements of Costa Rica back to our own Portuguese culture.

When we saw cows laying in fields, she was reminded of the many “happy cows” you’d see in the Azores. She’d point out a flower and say she had seen similar ones growing in Madeira. We popped into a Catholic church in a small town, and lit a candle for people we had lost. Grandma’s full name is Maria Helena, and she often goes by her middle name. That made for a really fun afternoon having lunch and exploring a town called Santa Elena.

I’ll always remember how good the coffee was, but I’ll always feel my grandmother’s smile when I see a hummingbird or butterfly like the ones that zoomed past her on this tour.

Friends in small boat

Final Verdict?

This trip was priceless, and it is going to live in my heart for the rest of my life. And I’m so thankful that my grandmother enjoyed it as much as I did.

I think our next lunch date back home might include a discussion about a tour to Croatia

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