Pet Sitting Disasters: Read This Before You Apply for Your Next Pet-Sitting Gig.

Sharing is Caring!

As an expert in getting free (or very cheap) accommodation around the world, I’ve done a good bit of pet-sitting and house-sitting. Some of these gigs were absolute paradise. Which is good, because they balanced out some of the pet-sitting disasters I also survived. 

In Panama, Guacamole the parrot flew away, despite the homeowner’s instructions to open her outdoor cage daily with assurances that she wouldn’t fly anywhere even though her feathers weren’t clipped. The dog also developed a nasty case of fleas, which necessitated not only treating the dog but also the very expensive rug the dog loved to roll around on (and I ruined the rug in so doing). I wasn’t held to blame for either of these losses (the parrot or the rug), but I felt bad and it was pretty stressful. 

In Grenada, the job was billed as watching the dog, but it was really about watching the employees (whose jobs were actually to watch me). All this surreptitious watching aside, the dog ended up in doggy-hospital and almost didn’t survive (the dog, that is. Though my own life also felt tenuous at times with a glorious bout of dengue fever + heartbreak). 

And in Japan, the cat in my charge was certifiably crazy who could, when not taking a swipe at my ankles, puke and poop at will. We got into a tiff one day, and while I was cleaning up the angry poop he left on my yoga mat, he puked on the bed.

I’ve got a few other dramatic tales of pet-sitting, but I’ll stop there. Why? Because they utterly pale in comparison to what you’re about to read. 

Pet-Sitting disasters! Petsitting is a great way to get free accommodation and experience the comforts of home while you travel. But heed this cautionary tale before you accept your next gig! #housesitting #petsitting #freeaccommodation #TheProfessionalHobo #traveldisasters

Tom Bentley is a colleague and friend of mine with whom I became acquainted in the Florida Keys. He is a business and travel writer, an essayist and a novelist. He’s published hundreds of freelance pieces in newspapers, magazines, and online. He is the author of three novels, a book of short stories and a how-to book on finding and cultivating your writing voice. He would like you to pour him a Manhattan right at five. See his lurid website confessions at

Tom and I were chatting about how the pandemic has curtailed our travels, and he especially mentioned missing his pet-sitting adventures. Which got us on to how talented homeowners can be in not disclosing everything about a house-sitting gig, thus luring us unsuspecting travelers into situations we might not have agreed to if given a chance. 

We’ve both learned a few lessons the hard way; lessons you can learn in advance (and thus avoid  experiencing the consequences of) here

Want to see just how hairy (literally and figuratively) a pet-sitting gig can get? Read Tom’s tale here. This article was originally published on a now-defunct publication called BluntlyMag. I asked him if I could republish it here because I enjoyed it so much. I hope you do too. 

Pet-sitting on the Road: Do I Need a Vet or a Shrink?

Pet-Sitting Bentley the Diapered Dog

The dog’s name was Bentley. I should have known there would be trouble, because my name is Bentley too. And though I don’t poop on the carpet, I have some anxiety issues as well. But I’m getting ahead of myself, so let’s anchor: for years, my girlfriend Alice and I have house-sat all over the world, for a month or two at a time. 

Panama, Hawaii, Ecuador, the Bahamas, the Caribbean, Mexico, lovely places all, where the setup is that you stay rent-free in exchange for taking care of the house, the garden, and often a pet. Or two pets or four pets or more pets. As a rule, prior to arrival, the owners will give you a bit of information about the animal and its care. 

As another rule, though unspoken, we have found that the owners have neglected to mention some minor matter—say, that the dog might need to have its anal glands manually expressed—that might have given our house-sitting promise a pause.

We’ll get to inflamed glands later, but let’s talk about Bentley, our Oahu charge. Bentley’s owners had explained by Skype that because Bentley had some anxiety issues about being left alone, and that he expressed that anxiety by peeing or pooping as soon as the door was closed, he had to be diapered. 

OK, that seemed a mite odd, but we could do it. What we didn’t know was that Bentley’s diapers would only corral his pee. And that Bentley would invariably—remarkably, distressingly—poop anywhere in the house (except on the positioned poop pads that were supposed to entice him) pretty much anytime you left. So, we learned that whenever we returned from even a short excursion, we had to search the house for the prizes Bentley left us.

We also didn’t know that Bentley needed to have a Prozac pill put down his throat every day, in order to quell said anxiety. This is something one has to practice, since pill placement is tricky, and pill spitting frequent. Bentley, who is actually a charming dog, is a toy poodle with soulful, mournful eyes; if you were sitting on the couch with him, he would lock eyes with you for long, expressive moments. Because he didn’t like to be watched while he ate, he would train those woebegone gazes upon you with deep meaning until you looked away, when he could then eat unimpeded.

house-sitting Billy the depressed dog

But Bentley was easy compared to Billy. Ahh Billy, our Caribbean island companion whose anxiety made Bentley appear the laughing Santa Claus of dogs. We’d been told Billy had specific food requirements at specific times: no dog food, but cooked hot dog in the morning, deli meats and cheese in the afternoon, cooked hamburger at night. What we weren’t told was that Billy wouldn’t eat his food. Since most dogs will eat socks, plastic Easter eggs and road maps, we thought this was unusual.

Offering him food made him visibly depressed. We would show him his food and his face and sunken body language spoke loudly of his sorrow. He once went 36 hours without eating—we went mad trying to think of a remedy. He would also howl like the hound of the Baskervilles when we left the house for walks, and we could hear it echoing through the hills.

His dietary habits were unsettling enough, but another of his neuroses extended to thunder and rain. Any time there was a thunderstorm, even a mild storm, or if the wind nosily arose, he would tremble for literal hours, and glue himself to your side. 

Since Caribbean islands regularly have weather squalls, that was a lot of side-gluing. Once he was tucked up against my leg trembling so violently that I thought he was having severe seizures, and because there was no vet on the island, we thought—to our terror—that this was the night he would die.

We were pleased that he didn’t die, because Billy, like Bentley, had a fair amount of likability tucked between his anxieties. Alice and I were also pleased that neither of us died every time we went into to kitchen to prepare his food and saw on the counter the latex gloves and medication  to express Billy’s anal glands if they became inflamed. The only thing that became inflamed was my panicked imagination, and that was enough.

Pet Sitting Four Crazy Dogs

You would never think that taking care of a neurotic dog was a blessing. You would never think that—until you had to care for four crazed dogs. OK, prior to arrival we were told it was only two dogs, but as I say, homeowners sometimes have trouble with details. The first two Bahamas dogs, Churchill and Dolly, seemed pretty doggish at first, but that was a ruse: Churchill turned out to be a crafty Svengali and Dolly his assassin.

No matter what fence or gate or enclosure that we’d put Churchill behind or in when we left the sprawling property for island excursions, he would always be outside the grounds when we returned. And he lock-picked with a laugh: he seemed delighted to see our surprise when we ever found him out of bounds, racing merrily about.

Dolly wasn’t as clever as Churchill (though she could bark like an orchestra on meth), but she was brutally skilled in one talent: on every walk we went, down that white-sand beach next to those impossibly blue Bahamas waters, Dolly would find something to kill in moments. She would rush on to the sand, frenziedly dig out a large crab, and then snap it lifeless with her jaws. Every walk. That made her day.

We thought these two were quite enough, until the owner flew in Bruno from Florida. Bruno was a big bear of a dog, perhaps as old as one of the Pyramids. When we walked him with the other dogs, he lagged way behind, perhaps reading a long novel on his Kindle while he trudged along. When it was time for him to come in the house, Bruno couldn’t seem to cross a threshold of a door, hesitating, inching forward, drawing back, until he would burst through, long—long—minutes later.

So there were three. Until there were four, with the arrival of Fluffy, who was not. Fluffy, that is. Fluffy was rendered near hairless by a skin condition so he resembled a possum (ugh, that spindly black tail), and he expressed his affection for Alice by biting her heels with needle teeth from behind while we walked. When we tried to feed all four dogs (two of whom needed medication), it was a veritable circus act, for you had to protect one dog’s food from another, and they would all race from bowl to bowl in a hierarchy, some the banisher and some the banished.

pet sitting disasters with two Toucans

So, we managed four dogs—we could take care of any pets, right? Wrong. Oh, so very wrong. In Panama, there was only a single dog and a single cat, both of them reasonable creatures, though the dog had a freezer full of specially prepared foods we had to thaw and cook. But the toucans, two beauties in a large cage, required a bit more exertion, because the owner thought that all of that toucan evolution that allowed them to eat in the wild for thousands of years didn’t apply: we had to hand cut the mangos, papaya and watermelon that we fed them daily, pieces of which they would raucously flip all over the cage. 

The parrots required even more attention. The large one required the attention of you trying to prevent him from killing you, because he was a nasty tempered thing, always stretching his neck to give you a good bite. The tiny one, a beautifully colored bird of bright pastels, required our attention because he seemed to be dying. 

Painted Parrot

We had to feed him with an eyedropper, which didn’t seem to help his listless doldrum and near inertia in the cage. We only found out after we left that he’d been sold to the owners as a species of rare parrot, but he was actually a regular green parrot, hand-painted with paints that made him sick, though they faded with time, and he perked up. 

The deer, however, alarmed us the most, because, well, it was a deer. They had trapped Punkin (yes) and gelded it—not best for a deer’s mood—and put a harness on it. The deer was kept in a very large pen on their 40 acres, but the owner wanted us to walk him on the grounds to keep him in good shape. I saw the owner walking, arm muscles straining, this lunging, thrashing thing once, and that was enough. After they left, Punkin stayed in his pen.

Pet-Sitting Punkin the deer

And a brief nod to Margaret the dog on the Big Island who never had visible worms, but who had the charming daily habit of sitting up on her rear, and using her front paws to twirl herself around and around in full circles on the shag carpet to stimulate her nether regions. That was carpet I had started lying on to do stretches—no more! 

And I won’t elaborate on the cat in Mexico who couldn’t remember that you’d fed him minutes before, and would rush at you in the kitchen screeching for more food every time you entered, so that we had to carefully creep around, always, to try to get to the kitchen unheard.

I could tell you more tales of all these beasts and more, but I’ve gone on long enough. I love animals, and will sit them again just to see what antics they get up to. (And just so you know, my own cat is a genius). But understand this: If you keel over your bowl of ice cream one day at home, your loving cat will indeed eat you before you’ve even gone cold. Animals!

[Note: all the animals’ names, except for Bentley, were changed to protect the guilty. And the furry.]

Sharing is Caring!

Get the Inside Scoop
Receive a FREE 2-week e-course on Financially Sustainable Travel 
Featured Image

4 thoughts on “Pet Sitting Disasters: Read This Before You Apply for Your Next Pet-Sitting Gig.”

  1. Hello! It was interesting to read about your experience. You really have nerves of steel! As an owner of 3 dogs, I can say that sometimes it is very difficult to find a person who will look after them during my absence from home for a long time. I try to discuss everything before the person will look after my dogs, but there were often cases when the person who looked after my dogs did not want to fulfill a large part of his obligations. Once it happened that I had to look for a person right during my business trip. Be careful with your dogs and find the best candidate for them


Leave a Comment