Tales (or Rather Tails!) from the Road – A Year of House Sitting as a Nomad

My very first house sit was in the Central Valley of California. It was March 2021, and I had just made the big decision to give up my apartment of 20 years in San Diego.

It wasn't my first experience as a house and pet sitter, but it was my first one for a stranger- someone I had never met before entrusting me with their most precious assets – their home and their pets – in this case, their two dogs.

I had only met them on video chat and the phone- and applied through a website called House Sitters of America. It was about a 7-hour drive from San Diego, and I remember choosing it because I thought it would be on the way to Oregon, where I had decided to spend some time going nomadic.

As it turns out, I decided not to leave until summer, so this was just a road trip up Interstate 5 to the Central Valley. It would be the first of many house sits I have undertaken in the year, allowing me to move around and “live” rent-free for over a year.

I am not even sure where the idea first came into my head for house sitting. My goal was to live and work while traveling at the same time. Unfortunately, my plans to go abroad went awry because of the pandemic. People in my world were skeptical and didn't understand.

Most had paid for pet care before and didn't understand the housesitting concept where free pet care is in exchange for accommodations.

Nonetheless, I persisted and, in that time, I have experienced challenges, learned new skills, humorous moments, and most importantly, lots of pet cuddles! They each taught me a lesson that I will carry forward with.

The One Without the Microwave: Portland, Oregon

I often say I wouldn't eat if I didn't have access to a microwave, even though I know how to cook. So, imagine my surprise when I showed up at a condo in Portland, Oregon, with my favorite frozen meals from Trader Joe's and walked into their kitchen to discover there wasn't one.

My thoughts went right to my oatmeal and tea making. When I texted the homeowner about it, she immediately offered to have her mom buy one and bring it to me.

I considered driving 90 minutes back to my family's vacation home to borrow that one. But, I told her it was not necessary to do that. I had ironically left my oven food behind, thinking, “I don't want to use someone else's unfamiliar oven (I can barely use one as is).

A quick google search helped me find all sorts of instructions on cooking microwave meals without a microwave. I also managed to heat my tea and oatmeal by using a plug-in water boiling pot. It's funny because I did another quick one in Portland on another weekend, and that family didn't have one either!

Moral of the story: well, there are two, actually. 1) You really can google anything! 2) I now ask the homeowners (if not stated in their ads) if they have a microwave. It's not a deal-breaker for me, but it helps me plan ahead.

The One with 5 Cats, a Huge Dog, and an Active Pit Bull

The ad for this house sits in a prominent and gorgeous neighborhood described as a Zoo. It also mentioned that Wally the dog was the determining factor in a house sitter.

If he disapproved, then you weren't the one. Who is Wally? Wally is an adorable huge Boerboel dog. It was an unfamiliar breed to me and probably to most. He is a 175-pound African Mastiff who, when he lovingly decides to roll over on your feet, could break a bone in them!

It's the largest dog I have ever seen or taken care of. But, despite Wally's large stature and deep bark, he's a sweetheart and loves his belly rubs. His pitbull sister Stormfly was a ball of energy and a little challenging to walk because she doesn't like other dogs (to the point that you have to cross the other side of the street away from them.)

I recall on one walk, a neighbor's dog had run out of the front door off the leash directly towards us. I yelled at the top of my lungs for them to come to get their dog because I was fearful of what she might do. And to compound it, it was only a kid who came chasing after the dog.

He was calling for his dog, but the dog wasn't listening. There's nothing worse than fearing a dog fight with a dog that isn't yours. Stormfly, to her credit, was listening to me and didn't attempt to fight the dog.

I will say she's a lovely dog; she needs her space from other animals and being a pit bull means she is very strong and a bit of a leash-puller.

There are also five cats in this household, and they are kept away from each other – the cats only reside on the second level, and Wally and Stormfly stay on the main floor.

I wasn't sure what I was getting into (add that with visits from the housekeeper, the gardener, and technician), but I have done such a good job they've had me back twice and invited me for a third sit as well.

Moral of the story: I learned about a new breed, how to manage a larger household with multiple pets and that I can take on more than I thought I could. The next challenge? Learning to drive a stick shift – they offer me their car, but I can't use it until I learn.

Best Buddies in Washington DC

In the first part of my housesitting journey, they had been exclusively on the West Coast. After planning a holiday trip back East to see family and friends—and the Omicron variant surging and busy schedules of my friends—I looked for a house sit in the D.C. area, where I had grown up in the Suburbs.

I lucked out when I found one in the Brightwood Park neighborhood for many reasons. First, the homeowner had the entire basement floor set up as a guest suite. She loaned me the use of her car (useful for two trips to the suburbs), but lastly and most importantly, her pet pair are my absolute favorite to date. Bernie the dog and Xander, the cat, just adore one another.

I had a dog and two cats who got along, but not to this extent. Xander, the cat, would follow Bernie and me on walks and made me nervous when he stayed out late in the night in the cold (even though she told me it was normal). When I wanted him to come back and calling his name didn't help, I would send Bernie out into the side yard, and sure enough, Xander would magically appear!

There was nothing like the presence of his best buddy. They would cuddle together with me, and no pair has shown more love for each other for a strange human! I still smile when I see their photos and remember our time together.

Moral of the story: Dogs and cats indeed can be best friends.

The Walk of Shame – An Unexpected Early Arrival

This housesit in San Diego is jokingly referred to as the “walk of shame” house sit. Most of my San Diego housesits involve busy work schedules. I was working my regular gig at the stadium when I received a text from the homeowner informing me they were coming home a night early, skipping their last planned night on the road.

The location was in the more northern half of the County, so I would have a long drive home after some hectic days on the road. The homeowner's early return now moved my plan to come back and rest that night and arise early the next day to do my final cleaning, pack up and then leave for another work shift.

Tired and hot, I now didn't have the luxury of that time. The homeowners would arrive after midnight when I knew I would be asleep, but I wanted the house back in order and most of my stuff packed back up in my car.

I still had food left in the fridge and freezer. With their late arrival, I didn't expect them to be up by early morning, bright-eyed and ready to be social—yet there they were. Weary from a long week of work, I was not either of those things, and I am not a great morning person. I only had met the one homeowner, and now he had her daughter and son-in-law and a dog with them (my care was only for the cat).

All I wanted was to gather the rest of my things and leave for my drive and workday, going “walk of shame” style. Instead, I had three bright-eyed people saying, “Good morning, nice to meet you.”

I did very much enjoy my stay in her lovely home, but that moment is one I will not forget as I felt disheveled and not cheerful.

Lessons learned: Expect the unexpected, and I now do most of my cleaning and packing back up the night before a sit ends. I am thankful for the heads-up instead of a surprise moment. On another housesit with a homeowner present, I accidentally saw one of them in their underwear! Thankfully I don't think they knew that I did.

The One with the Snake (and the guinea pig)

With a “gap night” in my schedule and for the fun of it, I applied for this far North County housesit that was only for one night. I almost didn't because of one thing: their listing included a pet snake in addition to their two dogs. I am terrified of snakes. I don't even particularly appreciate looking at them.

While guinea pigs are not my favorite either, the couple assured me I would not be caring for the snake and only needed to toss food into the guinea pig cage.

They wanted me there for the dogs so they could get away for a quick two-day motorcycle trip. Upon arrival, they showed me the guest room I would be staying in, and to my shock, it was also the room the snake and its cage were in!

I am sure my face fell at that moment. I sheepishly asked if I could cover the cage even if the snake usually hid under the cardboard box in the cage. I still insisted, and they complied with me. Once they left, I knew I could not sleep in that room!

I did spend most of my night on the couch with the dogs. However, when I did head into the bedroom, I spied that the snake had come out and was slithering. I could see the side of the cage – I found something else to cover it with and did manage to stay in there – albeit nervously.

Lesson learned: I managed to conquer my fears, although I am not sure I will do more reptiles anytime soon.

The Connections You Make

For me, the experience of housesitting has been a vital part of my nomad life over the next year – in at least a dozen different homes with all types of furry creatures. It has allowed me to travel and experience life like a local and often be in a home with amenities that my temporary home didn't have.

After losing the last of my pets during the pandemic, I also have gotten to love other people's pets as my own. In most housesits you only meet the homeowner virtually or on the phone before the sit. However, there have been times I have had the opportunity to spend time in person with the homeowner and pets.

One couple on the Oregon Coast invited me the night before and treated me to a nice dinner before leaving me with their two dogs and two cats in their amazing oceanfront home, where the waves crashed from the main room.

The connection I made with them is not one I will soon forget and allowed me to explore an area of the Oregon Coast I had never been to before. However, the best connection I made was in the adjacent town on the Oregon Coast, where I was temporarily staying in an ancient family cottage.

I jumped on the opportunity to house sit local, and I met a wonderful fellow artist. She led me to reside in the bottom half of her duplex during the offseason, so I could enjoy more amenities (and heat) than my family home has and stay in one place longer.

As a result, I can freely come and go without worrying about my belongings or incurring any costs. Trusted Housesitters brought us together, where I have found most of my sits, but are forever linked as neighbors, friends, and fellow artists (she paints, I am a photographer).

These are just a handful of stories from my first year as a nomad and my first year as a full-time house sitter. I have now house sit in three states and D.C. and have several more planned for the summer.

I have gotten to enjoy more than two dozen wagging tails and purrs, binge-watched shows on big-screen TVs, explored the vegan culinary delights of different areas and enjoyed a small piece of each owner's life and style while in their homes.

I know my tales are far from over as I continue this journey. And I know it will include many more tails and smiling faces. So I am looking forward to seeing where the road will lead.

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Featured Image Credit: Pexels.


Kelley Dukat
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Kelley Dukat is a freelance writer, photographer, and event planner currently based in the United States. She has spent the last year as a nomad travelling and house sitting. She holds a Journalism degree from the University of Colorado at Boulder and previously served as a trade magazine editor. Her favorite include dog friendly travel, road trips, nomad life. She is currently working on a memoir, and a series of personal essays.