When you’re 27, life on the road is as good as it gets.

As soon as you check into your hotel, you dump your bags and head for the nearest pub to find out where all the action is. When you’re 37, you get in and check if they have all the sports channels you need, and if the room-service menu is adequate. When you’re 27, you stumble back to the room at dawn with wistful thoughts of the leggy Brazilian you were too shy to approach. At 37, you are back in your room before midnight so that you can be on FaceTime to see your little baby’s spit bubbles.

It’s a great life, and also an incredibly lonely one. For every amazing night spent on Darling Harbour in Sydney or the Waterfront in Cape Town, you have five others spent staring at the walls.

Or you watch The Dancer Upstairs (obligatory Javier Bardem plug) for the nth time, while binging on sausage rolls picked up from the 7-11 downstairs.

On the dark days and nights, you keep yourself going by telling yourself that a million others would love to do what you do. Let’s face it, how many other jobs allow you to sleep till noon on some days or not work at all on others? How many other men get paid to watch live sport?

The best part of the job is getting to meet your heroes. One afternoon at Antigua airport, a man dressed all in white was checking-in ahead of me. It was Viv Richards, and I had him all to myself for an hour in the departure lounge. I kept pinching myself discretely to make sure it was real.

I’ll never forget Hallam from Barbados, his booming laugh and the encyclopaedic knowledge of cricket and sleaze. Hallam could describe every stroke that Lawrence Rowe played on his way to 302 against England. He would also tell you the names of each stripper performing at the Matador on a Friday night.

The morning I was leaving, he arrived half-an-hour early, and insisted that I get into the car straight away. As I worried about serpentine check-in queues and excess baggage, he stopped the car outside a cemetery. “You cannot leave without paying your respects to Macko [Malcolm Marshall]," he said. He was right.

In Kingston, while working round the clock on Bob Woolmer’s death, I bumped into Donovan outside the hotel. “Sit and talk to I," he said, his Rasta locks as grey as the Manchester sky. Once he figured out that I was on the island for the cricket, he came up with his proposition. “If you take me to this club, buy me two Red Stripes and a lap dance, I’ll tell you everything you need to know about Collie."

O’Neil Gordon Smith, Collie to those who knew and loved him, died in a car crash in Staffordshire in 1959. Sir Garfield Sobers was his fellow passenger. Jamaica has never stopped mourning him, and despite being in excellent spirits after the beers and five minutes with a voluptuous Grenadan, Donovan’s voice would break each time he spoke of the contemporary he looked upon as a saint.

Sometimes you meet people purely by accident. I came across Nicole in the crowd at Newlands, when I’d gone down to meet a friend. A political science student, she then came with me to Robben Island. I went there, like almost everyone else, to see Nelson Mandela’s cell. On the ferry back, all I could think about was the little house where Robert Sobukwe, a forgotten hero, had spent years in solitary confinement. Without Nicole’s expert guidance, I would merely have had a tourist experience no different from thousands of others.

So, while I’m eternally grateful for having watched the Laxman-Dravid show at Eden and the Miracle of Istanbul, I cherish equally a trip to Bassline on a cold and rainy December night in Johannesburg to watch Tidal Waves rock a large room that had 12 people in it. With a plastic cup of Jameson in your hand, those are the days and nights you remember.

Dileep Premachandran is a leading cricket writer and an expert on the game in India. He is an associate editor of Cricinfo.

Respond to this column at feedback@livemint.com