Tom Cahalan has a taste for the finer things in life.
The globetrotter, who made his fortune in the software industry at age 22, admits to spending hundreds of thousands of dollars a year on five-star hotels.
He now owns luxury travel company Dorsia Travel, which designs exclusive holidays for some of the ‘biggest names in tech, media and sport’.
The average Dorsia holiday costs around $125,000/£94,000 and is tailor made to its ‘clients’ exacting requirements’.
In an exclusive chat with MailOnline Travel, 38-year-old Tom reveals the biggest mistakes a hotel can make and which surprising country has some of the world’s best luxury properties.
‘Making a hotel is easy, making a bad hotel is very easy, making a great hotel requires every element to work perfectly,’ says Tom.
The demanding traveller explains that ‘overpromising’ is one of the worst errors a hotel can make. He says: ‘I still remember a property in Madagascar telling everyone it was an exclusive private island and it had a brochure inviting guests to their world-class spa.
‘It turned out the island was very much open to the public and there was no (and still is not to this day) spa.’
Tom Cahalan has a taste for the finer things in life. The globetrotter, who made his fortune in the software industry at age 22, admits to spending hundreds of thousands of dollars a year on five-star hotels. He’s pictured above in Fiji
‘Making a hotel is easy, making a bad hotel is very easy, making a great hotel requires every element to work perfectly,’ says Tom
Another of Tom’s pet peeves is when a hotel fails to personalise a guest’s experience.
‘My first red flag is neglecting guest preferences,’ says Tom. ‘Some hotels gather massive lists of guest likes and dislikes and on arrival they’ve ignored it all. Not only do they waste my time, they set an expectation and fail to deliver on it.’
Next red flag on the list? Complicated light switches. Tom says: ‘I particularly hate when hotel rooms are designed like no one has ever slept in one before. You need a manual and PhD to figure out the light switches.’
For Tom, the perfect hotel starts with a ‘great hard product’. He says: ‘The building, the location, the furnishings – the stuff that is somewhat fixed. And it has to be backed up by an amazing soft product, which is the service and food.
‘You go to a hotel because the hard product lures you in, but you only ever return because of the soft product. You need great service that makes everything just feel effortless, otherwise you can get a pretty room almost anywhere.’
As for travel destinations, Tom reveals that the Seychelles, Switzerland, Rwanda and Kenya are the world’s most underrated luxury spots.
‘People must think I’m joking when I say some of the top properties in the world are in Kenya, but there are some extremely exclusive private homes there that deserve actual awards,’ he reveals.
But there’s one destination that Tom recommends leaving off your bucket list.
Tom loves Velaa Private Island in the Maldives (pictured above). He says: ‘It ticks all the boxes’
The Connaught (pictured above) was one of the first luxury hotels Tom stayed in and he met his wife there
The average Dorsia holiday costs around $125,000/£94,000 and is tailor made to its ‘clients’ exacting requirements’
‘St Tropez. I don’t get it, it’s just a small village with a load of LVMH shops,’ he claims.
The worst hotel Tom’s ever stayed at
Giraffe Manor in Nairobi, Kenya, is a boutique five-star hotel that’s home to a herd of wild giraffes. It’s even featured on the BBC’s Amazing Hotels, but the quirky property failed to impress Tom.
He says: ‘The hype around it is incredible. I sometimes travel with my dad – whose version of luxury is whether they have chips on the menu – and even he hated it. It’s just like staying in a zoo, but somehow worse for both the humans and animals.’
Tom’s five favourite hotels
Arijiju, Kenya – ‘Someone’s private home, converted into a luxury lodge. The real heart of the property is the wonderful service by the managers, Rich and Della, but the property itself is stunning, having been built into the landscape to make it almost invisible. Five bedrooms, a cinema room, boot room, heated pool (that elephants sometimes come to drink from), squash room, tennis court and better than all that, it’s on a private concession with the amazing nature that Kenya offers, from lions to endangered rhinos.’
Velaa Private Island, Maldives – ‘A billionaire loved the Maldives so much that he had the arrogance to think he could build somewhere even better. And he was right. You can tell it’s a no-expense-spared, passion project of a property. It ticks all the boxes: amazing service, incredible food, beautiful island, two spas, all mixed in with lots of activities, loads of water sports toys, and a teen club and brilliant kids club. It’s even got a nine hole golf course there.’
Ol Jogi, Kenya – ‘I described it as looking like the Addams Family designed it – whilst on mushrooms – but this 11 bedroom exclusive use property is utterly unparalleled in the opportunities it offers. As a guest, it’s just you and all 58,000 acres, which includes a chance to spend time with habituated elephants, rhinos and baboons. The landscape feels like walking through Mars, and the experience often feels like being on another planet, with the house having hidden rooms and secret tunnels.’
Singita Sasakwa, Tanzania – ‘Probably the finest safari lodge in the world. It sits in Grumeti, on a 350,000 acre private concession, and is positioned perfectly for the Great Migration to pass right through. It makes for incredible sightings, with a seemingly never ending supply of lions and hyenas. But as you’re on a private concession, it’s just you and the other Signita guests, which is a far cry from the battlegrounds of the national parks, where you can have an army of vehicles vying for a single sighting. Once back in the lodge, you have a beautiful, luxurious, colonial cottage awaiting you, with some of the most breathtaking views of the Serengeti. Tennis courts, a gym, spa, heated pool, library and media room all add to it feeling a privilege to stay here.’
The Connaught, London – ‘I met my wife here, I am legally obligated to include it. One of the first luxury hotels I stayed in, and perhaps the most significant. The rooms definitely need a refurb, but the location and heart and soul (corny, I know) of the place means I always love it. It has an atmosphere that no other hotel in London has replicated, which is to feel extremely welcoming, but also exclusive. The food, including the patisserie, are world class, the spa is probably where they should bury me as I’ve spent so long in it, and I’ve known people here now for over 15 years. It’s great with children, it’s great as a couple, it’s a wonderful hotel that others will study, and few will ever replicate.’
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