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Costa Rica House Sitting with Jackie Kennedy(s)

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Costa Rica House Sitting with Jackie Kennedy(s)

A former NYC fashonista, Tim had spent his working life coordinating multinational projects for some of fashion’s biggest brands. He had taken clients to meet the Pope, curtsied before the Queen and regarded Gianni Versace as a close friend during his career.

Now, making his way out of the kitchen he’s a Jackie Kennedy (vodka, tonic and cranberry juice) in each hand. Wearing tailored trousers and a linen shirt he glides over towards me and hands me a glass.

Ben takes the other and gives me a wry smile. It’s just after lunch and he’s well aware I’m not very adept at handling my liquor.

I take a sip and have to stifle a cough. The alcohol content is obscene and it hits my blood stream almost instantaneously.

Outside the humidity of the tropics is pressing down on the world, but in here the climate control is set and a cool breeze is circulating around me.

Just 30 minutes ago I was out in the surrounding jungle walking Jack, the golden retriever whom Ben and I are pet sitting at a property further along the road.

I say road, I should probably note that it’s actually unpaved, more of a track. Winding its way up from the coast through the tiny village and then onto the mountain side, it stretches further into the jungle forking off in various directions to farms and remote lifestyle blocks.

As we chat about life, Tim’s past and our current nomadic existence I soak up the interior of the room. Plush furnishings, 1960s inspired design and vintage furniture combine in a vibrant display of personality and charm.

In comparison I feel quite out of place. I’m wearing an old pair of shorts and a singlet, my hair is scrapped back into a pony tail and I’m rosy cheeked still, despite having recovered from my jungle walk.



Ben playing with Jack by the pool at our assignment in Costa Rica

House Sitting Gives You More

It’s moments like this which make me realize the value our house sitting assignments bring to our travels.

Travelling the world and utilizing house sitting assignments to subsidize our accommodation costs has given us a much more immersive experience of the locations we visit. Not only do we get to sample local life but we meet local people, next door neighbors and friends of the owners who all have their own stories to share.

A little over 3 years ago I’d never heard of the concept, and certainly wouldn’t have put any money on the fact that a stranger would invite us to care for their home while they went away on holiday.

It was while we were planning what I thought was going to be a 12 month round-the-world travelling stint, that house sitting first crossed our radar. We knew we wanted to visit New Zealand, America and Australia, but with the cost of living in major cities like Melbourne at such a premium I wasn’t sure how we would afford to.

We toyed with the idea of following in the footsteps of a number of our University friends and heading out to Asia, where 10 bucks will buy you dinner and a bed for the night. However I was a little apprehensive; a little afraid of the cultural differences we would find.

I’ve never really been a typical 20 something traveler. Late nights, boozy parties and hostel dorm rooms are not my style, but in much of the western world hotel rooms are way out of my budget.

In hindsight my fears weren’t necessary. Travel has given me the opportunity to broaden my horizons and learn more about the beautiful planet on which we live.

Without diversity the world would be a pretty boring place.


Iguana relaxing on a branch in Costa Rica

House Sitting Abroad

Ironically house sitting threw me head first into the culture shock I had been avoiding.

After researching the concept Ben and I decided to try our luck and register as house sitters. Signing up with we created an engaging profile and spent a week searching for assignments, applying for those we felt would suit our skill set.

Italy, France, Australia, Hawaii, Singapore…the list of locations was endless.

Finally I stumbled on an advert for a property in Costa Rica. An eco-build, it was home to a young family who were flying back to the USA to visit relatives over the summer. Something about the ad made me apply…perhaps the photographs or the description I’m not sure.

The owner made it sound like a little piece of paradise.

waterfall-liberia-costarica_0Ben relaxing by a waterfall near our Costa Rican house sit.

Three weeks later we had secured the assignment and booked our tickets to Costa Rica. Little did we know it was the start of a life changing journey.

Since our first gig as house sitters we’ve looked after a further 16 properties. From the USA, to Canada, Australia and New Zealand our decision to accept an assignment in a location which first scared me somewhat, has offered us the chance to start a new life.

A life of perpetual travel.

Just as we met Tim in Costa Rica, we have made the most unlikely of connections as the result of our assignments. Connections which have led to lasting friendships and further opportunities to travel and house sit.

My memories of my stay in Costa Rica remain with me and serve to remind me that I should embrace the opportunities which pass my way.

You just never know where you might find yourself, or who you’ll be drinking a Jackie Kennedy with next.


Charli Moore Author Bio – Charli Moore is a house sitter and travel addict with a penchant for dark chocolate. In 2011 she and her other half Ben waved ‘Adios’ to the corporate world and jumped head first into a life of perpetual travel. You can follow the adventures of this writer/photographer team over at Wanderlusters or find them on Twitter and Instagram.



  1. I had a neighbor who paid me to house-sit their home while they were away on vacation. It included taking care of their pets which I really enjoyed.