At the beginning of 2024, Jonathan Hill sold his IT services company, which at its peak employed 50 staff members, after the business suffered during the pandemic.

He started producing video content from the ships he sailed on during his "year off" in 2024, which quickly gained the attention of My Kind of Cruise chief executive Sefton Monk, who spent months persuading Hill to join his agency, telling him: "Why don't you earn a bit of money so you can go on more cruises?"

After joining My Kind of Cruise last year, Hill hoped to sell a cruise a day to fund his cruise habit – a feat he has managed for the whole year.

Hill revealed he currently has six cruises booked – including a two-week Greek Islands sailing on Princess Cruises' Sky Princess vessel this summer – in the next 12 months.

"Really, I do 20 or 30 hours of selling cruises in a week – it suits my lifestyle really well," said Hill, who also manages a local care home's IT requirements. "Even just doing 20 hours a week for My Kind of Cruise, I've been able to sell nearly 450 cruises."

Despite his affection for Princess Cruises, Hill reveals that Virgin Voyages and MSC Cruises bookings amount to half his overall sales so far. Virgin Voyages has even invited to Hill to an awards ceremony this month owing to the sheer volume of cruises has booked in the past 12 months.  

Credit: Jonathan Hill

Hill estimates around 5% to 10% of his bookings come via his social media channels, with the rest coming from leads Monk shares. "Those leads are generally people who've gone on the website and haven't completed their booking for some reason," Hill explained.

"It's my job to follow those up and offer to help them. There's a heck of a lot people who don't really understand cruises and how they work – we're there to help and guide them.

"Sometimes, I may contact someone or be contacted 40 or 50 times to get a booking over the line. It might just be they're new to it but then they come back and book another six cruises with me over the next year."

'I made a mistake with one booking'

Hill outlined the difficulties in being able to give an exact number of bookings. "We get a real mix of cruise leads that come through," said the Hampshire-based homeworker. "We're traditional homeworkers in the sense we get leads from [My Kind of Cruise's] system and follow up those leads. I'm lucky to have a slight audience on social media, but even then, we're only talking 10 or 20 bookings."

However, it hasn't all be plain sailing for Hill since he started his new career. "It was a little bit overwhelming for me for the first month or two because there are so many different cruise lines and so many different rules and booking systems that you have to learn," he said. "There are also a lot of rules around adapted cabins for passengers with disabilities."

Hill continued: "I made a mistake with one booking. I'd put them in the right cabin but I had not applied for an evacuation chair. This allows them to get on and off the ship. If you don't book that chair, they could be denied boarding when they get to the embarkation point. It's quite serious. Luckily, the passenger had been on so many cruises they told me to double check with the cruise line."

Hill hailed the sales support teams at cruise lines. "You ring them up and speak to them. There are some lovely people at the cruise lines. At Virgin Voyages, there's a small team so you get to know them. They're normally quite good if you make a mistake," he continued.

Next sales goal? 

So what does Hill want to achieve over the next 12 months? "I'll be happy if I can achieve that million pounds in sales again. It is a good figure to hit," said Hill. "I'm only a very small part of My Kind of Cruise. I have another job so my income is all covered. This is extra income that goes towards funding more cruises so I can learn more about it and sell more of them."

Hill insists he has no desire to work more hours to increase his booking levels. "My target was a booking a day and if I could hit a million by the end of the year, I'd be really chuffed about it," he said. "That is what I achieved. I do think it's possible to do more if you want to. There are about 10 agents at My Kind of Cruise who are properly full-time. It changes quite often."

Hill said other new agents who may want to sell lots of cruises need to go on "some actual cruises". "Then you're able to answer so many more questions," he added. "I think anyone can do it as long as you're bubbly and honest with customers. All they're looking for is honesty, facts and a friendly person. If you have those things, you'll be fine."