"We had budgeted for two nights at a marina per month. So far, over 90 nights," he said.
"Due to every government office in Greece being closed during the Covid-19 lockdown, our final yacht purchase papers went on hold. The marina was locked. We went on hold too."
Silke and the two children travelled on German passports and Tim travelled on a Kiwi passport. It means he's now technically an overstayer.
"So my Schengen visa was going to expire, we started trying to find anyone to help extend it," Tim said.
"Dozens of unreturned emails and unanswered phone calls were made to no avail. All the government websites were, of course, in Greek and Google translate really didn't help much. Greek consulate in New Zealand couldn't help. Neither did the New Zealand consulate in Greece (based in Rome).
"We rented a car to get to an immigration office some distance away. Even though the website said they were open, they were not. [We] rented a taxi the following week. They were open but seeing no one."
A local, finally, tracked down a local immigration office and they got an appointment.
"By now I was four days overdue and simply told because I was overdue and red flagged I now had to leave the country immediately," he said.
"Even though there were no flights, I have no home to go to and our yacht is still locked in the marina with no paperwork to finalise the sale.
"First month overdue is a 600 euro fine, second month 1200 euro, third month I'm black-flagged. Without the paperwork we cannot sail even though we actually own the yacht."
Tim said Maritime NZ were "amazing" with its paperwork for New Zealand registration.
"It looks like we are going to have to pay the boat tax office (yes that's what it is) some money under the table to get something sorted to leave for Turkey and hope we don't get black-flagged in the meantime," he said.
"We now are going to try to get a lawyer to speak with the Minister of Immigration in Athens as we found documents signed by the Minister of Immigration that seem to indicate that we should have an auto-extension of the visa.
"Trouble is, the people who want to fine us are not convinced. We can't afford the fines, we can't afford the marina, we can't afford the lawyer."
On Monday evening, NZ time, the family was still stuck in Greece, Tim said.
"No final paperwork due to Covid, expired visa due to Covid, big fines looming."
The family's situation caught foreign media's attention and they were interviewed by Greek TV and a German radio network.
"We will see what this week brings, we may end up paying the fines (if the yacht papers come through) and high-tailing it to Turkey (a non-Schengen country)," he said.
"But there are no plans to return to Hawke's Bay yet, we are fully committed to this adventure."