The connoisseur: Philip Blackwell

If I didn’t live in London, I would live in Sydney for its vibe and lifestyle. I love the idea of leaving my desk and being on the starting line of the evening race 45 minutes later.

My greatest travel companion is a writer who has really captured the destination I’m currently in. I feel naked without a book somewhere to hand.

A great hotel should have great staff, with the emotional intelligence to anticipate interactions that leave a deep impression. But it should also have an intelligent selection of books and somewhere quiet where you can curl up to read them.

On holiday, I like to match my reading to the destination and create my reading list for a place. For example, if I was in Sydney I would read 30 Days in Sydney by Peter Carey, or something by Peter Temple, who is a great Australian fiction writer. He gives a sense of that place as well as taking you to parts of a country that you wouldn’t necessarily want to go yourself, but give you an understanding of what makes Australia tick.

To destress on holiday, I switch off any electronic devices and sit and absorb the view, because a wonderful horizon – whether out to sea or over the savannah – is a great metaphor for developing a strategic mindset. Then I pick up a book.

I make myself at home in a new city by getting out and walking, tasting the cuisine, soaking up the atmosphere and talking to the locals.

The thing I miss most when I’m away is my own bed, my family and my dog, a black Labrador called Inca, who I go walking with every morning.

The most underrated destination is Transylvania. It’s a fascinating time capsule with unbelievably beautiful countryside, very friendly people and a great history. We came across a stand of oak trees that was planted 800 years ago by the Saxons who were originally brought in by the King of Hungary as a line of defence. And it’s got some gems like Sighișoara, which is said to be the home of Vlad Dracul.

The best souvenirs I’ve ever brought home, apart from my wife who I met on a skiing holiday in Méribel (kidding!), are the seashells I pick up when it’s not insensitive to the environment, such as a beautiful conch shell from a Tobago beach.

The last place I visited for the first time is Hawaii, the Sensei Lānaʻi, which is a long way to go but very rewarding.

The key to switching off on holiday is snorkelling and diving. I love entering a parallel universe beneath the water that takes you somewhere totally different. The casual interaction with marine life just grips me. The highest reef at Soneva Fushi is pretty special. Last time I dived, I came across turtles, sharks, rays – the full range.

I last had a memorable meal at Tobago Cays. We had fresh lobster on the beach to a reggae soundtrack during a sailing holiday. We dropped anchor and we watched a team of people 300 yards away spend hours setting up a platform, barbecue, umbrellas, a bar – basically a micro nightclub-cum-restaurant on the beach. Then a boat came across with people from a superyacht, who had a buffet dinner and then went home again two hours later while the staff dismantled the set-up. We ate a bit further up the beach from a wooden table and it was delicious.

I can’t wait to go back to the Maldives. Sand, sea and diving. You don’t get that in London or Oxfordshire.