Travel Confessions: Paradise Found in Bermuda


And so it begins!

We kicked off our year-long travel adventure with our first official trip to…


Chris and I chose Bermuda when we learned it was an easy 2-hour flight from our hometown of Boston, Massachusetts.

Before Trevor was born, Chris and I did the 12-hour flight from Boston to Maui. All through the cold and brutal winter of 2018 – which seemed to never end! – we were daydreaming about those crystal clear waters and white sand beaches.

So our hope was that Bermuda might be a smaller, simpler replica of that Hawaii dream trip…

Here’s everything about how the first trip of our year-long journey went:

What Flying With a Two-Year-Old Was Like

Trevor handled the flights so well, it truly gave me courage to want to try longer flights in the near future!

He sat quietly – seatbelt fastened – for the duration of both flights (we didn’t want to take off his seatbelt, for fear he’d throw a fit when we had to put it back on for landing).

He mostly watched his favorite shows on the Kindle (we downloaded a few new episodes the night before we left).

When that got old, he played some number games on the Kindle, then watched videos on my iPhone.

In between, he snacked on pretzels and cookies and drank a couple of sippy cups of milk (milk is his absolute favorite, his go-to “comfort food”).

We got several comments from fellow passengers about how well-behaved he was, which made Chris and I so undeservedly, over-the-top proud. We must have done something right!

That being said, flying with a toddler is no joke!

Trevor wanted to run everywhere and explore everything in the airport.

Trying to get him to quietly wait in security lines and not dart into oncoming crowds with heavy suitcases – – it was all exhausting.

Also, I used to be sort of a germophobe.  Pre-Tru, I liked to scrub my hands thoroughly with soap before ever eating anything. I wiped surfaces, like my desk, frequently with anti-bacterial wipes. And I definitely avoided touching anything in the airport! I did all of this just to maintain a sense of security that I was protected from any terrible coughs or colds or flus going around.

But Tru, who I once found eating the dirt off the bottom of his boots, has kind of beaten those germaphobe tendencies out of me. I’ve just slowly had to let those rigid routines go, so as not to carry heavy stress 24 hours a day!

In the airport, Tru played with his favorite toy school bus to pass the time waiting for our plane to board. It kept him busy and quiet.

He would drive the bus along the terminal seats (which always look like they’re covered with a thin film of debris from 10 years ago). Then he’d drive it along the airport carpet. Then he’d absent-mindedly put it in his mouth. This gave me such anxiety. The germs!

I must have said the words, “Trevor take that out of your mouth” fifty times.

But I’m making progress on just loosening up on these things I can’t control. I’m going to have to, traveling for a full year with a two-year-old!


The Best Thing About Bermuda

The best thing about our trip was…

basically everything about Bermuda!

The island was just so, so beautiful. I thought the clear turquoise waters and soft, pink-tinged sands rivaled the stunning beaches of Maui.

Chris and I couldn’t stop saying how crazy it was that this stunning wonderland was only two hours away and we never knew! Right under our noses, paradise was waiting!


The one disappointing thing about the incredible beauty of Bermuda: I fear that our first trip of this year-long journey will be the most stunning of all.

The best may already be behind us, one trip in!

But if that’s my biggest complaint about Bermuda, you understand how incredible this island truly is!

My Fear About Traveling with a Toddler

The one thing that becomes crystal clear to parents of toddlers: they thrive on routine. Trevor likes knowing what’s coming next in his day, and I understand. Toddlers have so little control of their day-to-day lives.

Before starting our year of travel, my major concern was about disrupting his routine. And whether or not new surroundings would cause Trevor major stress.

So Chris and I tried to maintain Tru’s routine as much as possible.

We returned to the hotel each afternoon for his normal nap.

We brought along his favorite toy buses and cars.

We got a white noise app on our phones to mimic the white noise machine we play in his bedroom at home to help him sleep.

We packed his Halo sleep suit and three of his favorite books to read each night before bed.

And we made sure to pack a couple of his sippy cups, because milk is his favorite thing and it really relaxes him.


Overall, Trevor seemed to thrive with all the changes.

For example, we tried to stick to his normal sleep schedule. But due to all of the challenges of traveling, most nights we got Trevor to bed about an hour later than normal (8:45pm versus 7:45pm). And he handled the late nights like a pro.

He seemed mostly happy, engaged, and excited to explore his new world.

That’s not to say he didn’t have his fair share of tantrums and melt-downs. He definitely did!

And it’s tough when he starts fussing in a public place. For example, we boarded a public ferry to return to our hotel for Tru’s afternoon nap, and it was loaded to full capacity with tourists from a cruise ship. Trevor started squirming and crying because he didn’t want to sit still in his seat. It was stressful.

Chris and I did everything we could to calm him, but we started feeling the eyes of strangers on us. Were people looking with sympathy? Or were they glaring?

But here’s the thing: similar incidents still would have happened at home with our normal day-to-day routine!

At least in Bermuda, when Trevor threw a fit about having to get dressed in the morning, I could step outside and see bright sunny skies and crystal clear turquoise waters!

Our Most Pleasant Surprise in Bermuda

I should mention that our first big, wonderful surprise was the view from our hotel room balcony. Just crystal clear turquoise waters stretching in every direction for what seemed like miles. Our jaws just dropped the first time we walked outside.

But aside from that, we were also blown away by the friendliness and genuine kindness of all of the local Bermudians we met during our trip. We talked with several locals who had lived their whole lives in Bermuda, and they were all happy to tell us about their favorite local foods (codfish and potatoes on Sunday mornings, served with a tomato sauce, boiled eggs, and avocado) and celebrations (hundreds gather at the beach each year on Good Friday for the Bermuda Kite Festival).

One local Bermudian happily greeted Tru at the front desk when we checked into our hotel and quickly noticed he was carrying a toy school bus. Later in the week she greeted Tru with a toy pink Bermuda bus (the public buses in Bermuda are pink), and Chris and I were just blown away by her thoughtfulness and kindness. Trevor carries that pink bus with him everywhere now!

There was also an evening when we took a trip out to the town of St. George, and had asked our hotel to send a taxi to pick us up at 8pm. By 8pm, the town was very deserted and it looked unlikely we’d ever find a taxi, unless the hotel actually came through for us and sent one as planned. While Chris was struggling to keep Tru from darting into the street, I noticed a single taxi drive by and waved to flag him down. He zoomed right by me and I called to Chris, “I think that was our taxi that we just lost!”

A boy who must have been about eleven years old was riding his bicycle nearby and heard me. He said “oh no! That’s your taxi? I’ll go catch him!” He sped off in the direction of the taxi and returned a minute later saying, “I let him know you’re coming and he’s waiting up ahead.” He really went out of his way to help us strangers. Everyone we talked to had that same level of cheerfulness and decency, and it’s something Chris and I will always remember about Bermuda.

Regrets About Starting a Travel Journey, One Trip In

Making Bermuda our first trip was a good idea, I guess, since I have no regrets at this point!

Granted, I should make this distinction: Our time in Bermuda was a trip to a new location we’d never seen before. It was not, under any circumstances, a relaxing vacation!

But I never had any hope or expectation for lots of relaxation during our travels. I did hope to work on my photography skills and get myself out of my house and start seeing the world again. More than anything, I wanted to explore the idea, “what happens when you let your heart decide?” (to change my mindset from focusing so much on worries about the past and fears for the future.)

We all experienced so much laughter and fun on this trip, we met so many kind and wonderful people, and we saw so much beauty. Truly, it seems as though my heart has led me in the right direction so far!

Sweetest Memories of Our Trip

Bermuda is stunning in every way, so it was hard for Chris and I to narrow down our top memories, but here are some highlights:

Language Explosion – Trevor suddenly started putting words together and saying 2-4 syllable phrases on this trip. It was amazing to see his language burst happen in Bermuda! He loved saying, “big sand! Big, big sand!” (to ask to go to the beach), “blue van” (the hotel van), “pink bus” (the buses in Bermuda are pink, and we rode one from the beach to the nearby Fairmont hotel one morning), “green house” (the houses are all vividly candy-colored in Bermuda) and “bubble bath.” Oh, and “more pool!” Being the toddler that he is, he would have happily lived out by the pool!

Warwick Long Bay Beach – We visited this beach on what was, to me, the most beautiful type of day imaginable: about 72 degrees, no humidity, and clear blue skies. The beach was stunning, with soft white sands, clear turquoise waters, jagged rocks and swaying palm trees dotting the landscape. And we were the only ones on this beautiful beach during the time we spent there – it literally was our own private escape!

Sunset Sail – Chris and I weren’t sure if we should sign up for a sailboat ride while in Bermuda, because we didn’t know if Trevor could mostly sit still for 2 hours on a boat. We decided to go for it, and I’m glad we did. It was my absolute favorite part of the trip. Trevor was so over-excited about being on a “big, big boat,” he couldn’t sit still and was darting and squirming. But by the end of the ride, he had settled in. And we had the chance to sit back and take in the spectacular view. The island looked beautiful from that vantage point. The sunset lit up the sky in a burst of color and the vivid turquoise ocean was so calm.

Breakfast on the Balcony – We struggled through one breakfast in the hotel cafe with Tru squirming and fussing and refusing to eat. When we found out we could order room service for the same price, we decided to go with that option instead! They set up delicious waffles and smoothies (plus a sesame seed bagel for Tru!) on our hotel room balcony, which looked out over the most incredible stretch of turquoise ocean. What a way to start the day! Chris and I never order room service, so I have to hand it to Trevor for helping us to discover something we never would have thought of otherwise!

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