The time we turned down three months free lodging on a remote Greek Island

Who turns down three months free lodging on a remote Greek Island? I guess we do.

Coming off a summer of house sits around Puget Sound, we decided to expand our scope internationally. We knew we’d be traveling to Mexico for several months and after that perhaps Europe. I changed our search parameters on TrustedHouseSitters to include other parts of the world and house sits of at least two weeks. After all, if we were going to travel to a foreign country to house sit, we wanted to make it worth our while.

When I stumbled upon the 3 month house sit in Greece, I couldn’t believe it. The house was part of an estate with several cottages located on a remote island. During tourist season, the owner rented out the cottages, and the reviews left on line were amazing. People talked about having a private beach to themselves with water lapping at the shoreline just steps away.

This would have been the view from our cottage

The house sit listing suggested we would be staying in one of those cottages. It also stated a preference for a couple. With the two big dogs we’d be caring for, it made sense to want two sitters, but we later found there may be more to it than that.

Joan’s response when I mentioned staying on a remote Greek island for three months for free was “I’m already packed”. I put her in charge of the introductory communication with the owner as she’d been perfecting her persuasive writing skills for the previous year. 

The only problem was that the house sit started so soon that it would have overlapped one of our other sits. In her letter of introduction, Joan said we could do the 3 months but that we’d need to start a little later. We figured someone who was planning to take a 3 month vacation probably had some flexibility in their schedule. It turns out he did. He contacted us fairly quickly and requested a video chat.

We spent the morning of the interview familiarizing ourselves with the posting: his dogs, the responsibilities, the location. One thing I noted was that he said a car was necessary. That was a problem since we didn’t know where we would rent a car on such a small island, and it would probably negate the benefit of having a free place to stay. The owner did mention something about the possible use of a 4×4, but I’d have to inquire about that in more detail since the closest town I could find to the estate was 8 miles away.

The owner spent the initial part of our video chat talking about the dogs and the facilities. He then took a more serious tone asking me about my health. He mentioned that I might need to be a bit of a handyman as things occasionally came up like a leaky roof or a broken pipe. While I’ve done my share of home improvement, for the most part, I’ve usually had someone more knowledgeable by my side. I am capable but prefer to prevent problems as opposed to solving them.

Discomfort began to creep in as the owner asked us what temperature we preferred. He explained that winters on the island could be cold and wet. What he described sounded a lot like the winter season in the Pacific NW we were trying to escape. My dreams of driving around the island on the 4×4 to go hiking and exploring were turning to nightmares of driving a completely open vehicle through sleet to get groceries.

The owner explained that the cottage had a space heater, but it was unlikely to heat the space any warmer than 66 degrees. He also mentioned that the pipes had broken the previous year, and it had taken him a week to find the leak. I envisioned myself digging along the length of the pipe looking for the source of the leak, trying to differentiate that from the water pouring over my rain hat.

By the end of the interview, he suggested that the hardships were the reason he preferred a couple, but Joan and I had the same thought in mind, “The Shining”. We told him that we’d need a day to discuss the details and that we’d get back to him in 24 hours.

Not surprisingly, it wasn’t a long discussion. While the idea of three months on our own Greek island sounded amazing in theory, the reality of being isolated in Greece during low season was unappealing. I’d been to other islands during the off season and was amazed at how shuttered they were. Most of the people on these islands make enough money in the summer that they can close up shop for the winter.

We envisioned this not as an island paradise but a Greek tragedy, which is why I contacted the owner the next day to let him know that we would be declining his sit, though he was welcome to contact us regarding the next summer.