Travelling Solo: A housesitter’s guide

17 Aug, 2019

Travelling Solo: A housesitter’s guide

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At HouseSitMatch we find we are increasingly attracting more professionals and semi-retired professionals travelling solo or as couples and housesitters. Many want to pursue a long nurtured dream to travel. As is our want when we meet someone with an interesting perspective on ‘life, travel and housesitting’ we approach them to share their experience of housesitting through HouseSitMatch.

Here is Pam’s story, she’s Canadian professional and empty nester who on the graduation of her youngest child decided this was the moment to experience Europe first hand. She began her journey as a solo traveler by housesitting and pet-sitting for a homeowners in Maidenhead, UK.

Travelling solo for house sitters

From this location with just a couple of canine companions for company she experiences English life in the market town of Maidenhead. Enjoy her observations as housesitter and ‘flaneuse’…

Full moon shining over Maidenhead Bridge
Moon over Maidenhead Bridge walking everywhere while travelling solo

Travelling Solo: A housesitter’s guide

I love animals. Pets can be terrific companions.  But when you are travelling alone as a woman to housesit in different countries, it can be socially isolating without human contact.  Having a furry friend around is absolutely great, but talking to creatures who don’t answer back does have its limits.

Who am I the solo traveller

I am a middle-aged, single Canadian woman who is living out her dream of travelling solo and living abroad. I left Canada in January of 2016, lived in Mexico for four months, then travelled solo to Tenerife in The Canary Islands and finally to Madeira, Portugal, before arriving in Maidenhead, UK, in the middle of June.

Discovering Maidenhead

Street named Folly Way
Exploring side streets in Maidenhead

Maidenhead is a beautiful and affluent town just west of London in the Royal Borough of Windsor and Maidenhead, in the county of Berkshire. The population is significant at 67,000. It is the home of Theresa May, the newly anointed Prime Minister of the country. 

When I arrived in Maidenhead in June, the weather seemed more typical of April, with dreary grey skies, daily showers and chilly temperatures, setting a dark and dismal tone for my stay.

Taking up housesitters residence

I took up residence in the owner’s terrace house for a housesit which included the care of two canine companions, Bonnie, an 11-year-old Bouvier, and Duke, an 8-year-old Labradoodle. The housesit would be lengthy due to the hospitalization of the owner, who has a debilitating illness.  

The family of the owner was very kind, helping me with negotiating travel arrangements and navigating the town and surrounding areas. They showed me where the closest park is for walking the dogs and also where the vet is located.  

They had the house professionally cleaned on my first day and had new linens delivered to the house for my use. And then I was on my own. Travelling solo in a new town in a new country.

Getting to know the dogs

Two black dogs on leads
Bonnie and Duke
Dog sat on the grass
Trying out what I’d learnt

I spent the first few days just focusing on the dogs, getting to know them and letting them acquaint themselves with me.  I knew that they had been through a lot already. Firstly, the failing health of their beloved owner, who had to leave them suddenly, and then a series of other carers before me.

The dogs behaviour

Both dogs had separation anxiety and, although they had lovely distinctive personalities, they also had behavioural issues.  They cried whenever I was out of sight, and sometimes howled when I left the house without them.  

Duke pulled hard on the lead and lunged when being walked, and jumped up to the counter when food was being prepared. Bonnie behaved aggressively towards other dogs and was unpredictable when off lead. Therefore, she had to be kept on lead at all times outside of the house.

Both were very excitable and somewhat competitive, riling each other up whenever they were triggered by the slightest commotion. And even more concerning, both would attempt to lunge out into traffic and had no road sense. They also needed a really good grooming.

So I had my hands full and my mind occupied for the first few days.  Through video call consultation with a friend in Canada who is a dog behaviouralist, I got some important advice, which I applied right away and began to see results.

Key to travelling solo – Housesitters keeping in contact

During this time I had no internet service at the house.  The family of the owner had mistakenly assumed the service was in place, but it had been terminated. As for telephone service, there is a landline to use in case of emergency, and to keep in touch with the family about the dogs, but I do not have access to my Canadian mobile service outside of North America.

Fighting a sense of isolation when travelling solo

Therefore, my contact with the outside world could only take place in a Wi-fi-serviced café or public library in the town centre, which is about a 20-25 minute walk.  This was very socially isolating, and at times, I felt quite lonely. Clearly this was one of the downsides to travelling solo and especially solo housesitting

Eventually, I was able to secure Wi-fi on a monthly basis and the family graciously agreed to pay for it. This solved the problem of limited contact with family and friends (yay!) but still did not meet my need for human face-to-face contact.  So what’s a stranger to do in a town where they don’t know a soul?  

I have found a number of answers which have helped me get connected to the people in the community. This was essential in order for me to enjoy my time travelling solo! 

Meeting new people when travelling solo

Wimbledon final screening, one way to meet new people when travelling solo
Wimbledon on the Big Screen


Firstly, I try to find out what’s going on in town and attend public events, such as festivals, markets, car shows, sporting events and antique markets.  Many of the events are free to the public. During the Wimbledon finals, Maidenhead erected a giant video screen in the town square and set up chairs.

A local charity served strawberries with cream for a nominal fee.  I joined the community for the event, and although I was the only person cheering for Raonic, the Canadian, no one seemed to hold that against me (especially after Murray took the title).

Fruit market in Maidenhead
Local fruit market in Maidenhead

Coffee shops

Secondly, (and I can’t stress this one enough), coffee shops! Cafés are a place where people go to linger and take a pause out of their day. This is a time when they are a little more open to meeting new people than when they are more focused on getting something done.

I have met some delightful people in cafés, merely by asking a question, or commenting on some local news story. I find that people are generally quite open to helping a newcomer, and they are also interested in your alternative lifestyle as a housesitter, and someone who is travelling solo  because it is new and different.

Furthermore, if you frequent the same café regularly, you will see the same patrons and with familiarity, be able to first nod, and then maybe say hello. It is also possible to get quite chatty with the staff.

Pathway with arched trees
Discovering new dog walks

Use the internet when travelling solo! 

Finally, if these less structured environments aren’t working, there is a worldwide service online to connect people with similar interests. It’s called Meetup and I first tried it in my home city of Toronto when I moved to a new neighbourhood. The internet is a great way to meet others through solo travel groups, perhaps in social media.

Meetups are great when travelling solo

To access the service, go to, create a personal profile, type in the city in which you are located, and browse the groups.  You will find meetups for people who like all kinds of activities:  theatre goers, fitness fanatics,  meditators, hikers, fine diners, music lovers, yogis, and people who like to talk politics.  

Find one you like and add it to your list. It’s that easy! You can send a note to the administrator or wait to be contacted. You can look at what events have been planned and sign up for one. Sometimes there is a small fee, but often events are completely free.

These events are designed for connecting people of like interests in order to have company for an activity.

It is not a dating site! This was a great way to beat the (occasional) travelling solo blues! 

Petsitting while travelling solo

After a month pet-sitting Bonnie and Duke, I have settled into a regular and comfortable routine in Maidenhead. We are continuing to make good progress on bad behaviours, and I’ve made some very nice new friends.  

Solo travel has also helped me to discover something else about myself, I realise that I am a flâneuse (The Guardian – “a keen-eyed stroller who chronicles the minutiae of city life”, “that urbanite who is neither aloof from the crowd nor surrendered to it, but both at once.

Travelling solo – tick! 

Further reading about housesitting and housesitters

At we like to share useful blogs and practical advice about housesitters, housesitting and pet sitting. We hope you find this small selection of our blogs on house sitters and house sitting in London useful.

How to travel on a budget

Solo travel – House sitting is a safer options

What a housesitter does – Top 10 responsibilities

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