Book a bespoke vacation in just 10 minutes with this startup

Photo credit: Nick Kenrick

It was a hot June day, deep in the south of Spain. My mother and I had been walking around wonder-struck in the splendidly carved corridors of Alhambra, a 9th century fortress, when I noticed that she had disappeared.

We were already running late. The tour organizer was positively scowling even before I announced my mother was nowhere to be found. After a few minutes, she said the group would proceed without her. I was aghast. Had we signed up with a reputed travel company for a tour of Toledo, Granada, Sevilla, and Cordoba just to be abandoned like this?

My mother materialized just in time, turned up an imperial nose, and declared: “What? I was soaking in some history!”

This little memory from 20 years ago was nudged awake by something Hari Ganapathy, the co-founder of PickYourTrail, said about travellers of different kinds.

“Romance buffs might just decide to sit beside a river and enjoy a drink. Parents might need more time than average to visit a museum.” Precisely!

Photo credit: Thomas Hubauer

Thankfully, the 21st century makes bespoke travel possible – even if you are not royalty. It’s what Hari’s startup has helped over 1,200 people from 15 countries experience over the last two years.

From its base in Chennai, PickYourTrail has carved out vacations in 100 plus cities, with the planning, costing, booking, and management all taken care of. Its customers are mostly Indians living in Singapore, the US, and Dubai.

“Folks work their asses off for that one, awesome international vacation,” says Hari.

Made to order

Here’s what happens when a habitual traveller like Hari teams up with a biking and data enthusiast like Srinath Shankar. They go up the startup path, fall, learn, and take to the road again.

Both are MBAs, by the way.

“We started off as an experience marketplace. The idea was: what you do in a city broadly defines your overall vacation experience,” says Hari.

A giant pain in the butt

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