Why I’m Dreaming of Family Travel This Year

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With 2020 firmly behind and the 2021 summer around the corner, our hopes are on the rise for the resumption of travel this year. While grateful for being relatively COVID-safe in Singapore’s golden cage, the smallness of our island has us pining for the outside.

2021 and there are 227 inhabited Greek islands. Where should we even get started?

As they say in Greece, hope dies last. Under lockdown, I’ve combed through island after island, selecting our visions of paradise for the next three summers. By now, I’ve read every major travel magazine article, little known blog post, and forum review on the destinations of interest. Each island has a tab in my spreadsheet and a file on Instagram collecting information and inspiration as I go.

Finally, I have the luxury of time to plan a vacation. A true rarity for moms. And finally, I’ve found exactly what we’ve been looking for: stylish and reasonably priced vacation villa gems located directly on child-friendly beaches in mid-size Cycladic seaside villages. Day trip options for semi-private cruises to neighboring islands with out-of-this-world beachscapes. Where to send the kids for a pottery workshop while in Sifnos…Any trip from here will never be so well planned. And as parents with the load of baggage we carry, some volatile with surprises, invaluable is a seamlessly organized holiday.

The simulation of travel in the planning process soon became therapeutic escapism. From home, I visualized us on that beach house patio with a cool glass of Assyrtiko in hand. Slowly sipping, we watch the kids frolick in fine white sand as the sky changes color. Later, we take an evening to wander through cobblestone paths of whitewashed villages, alive with the soul of Greece. I deviate to shop online for kaftans. I think we will dine at a Greek restaurant tonight.

Sure, I may have to cancel everything a month before June but herein lies a precious exercise in non-attachment and letting go: There is meaning in learning to defer to forces beyond our control. So much of our days as parents never go as planned anyways. And if the process of pursuing an end result designed to bring happiness, instead dominates with anger and frustration, what then is the point of the whole endeavor?

Savor the planning, inhabit the surprises, heal if you must, and journey on. Enjoy the entirety of your travels, and consider 2021 an opportunity for the most well researched you, ever. Whether in a summer sojourn, or the journey of life.


A restless city-loving Singaporean learning how to be still, embrace the antithesis of her husband's Greek nature and homeland, and master motherhood. After moving from Athens, we now live in Chicago, and are set to return to Singapore for a proper village welcome of our second baby.