Pickyourtrail :Secret behind Customized International Holidays

Secret behind Customized International Holidays
HOLIDAY with pickyourtrail

Pickyourtrail has two friends behind this delightful travel tech. Hari and Srinath two friends from Chennai, travel lovers who bootstrapped a startup which won Google’s Customer delight award in 2017. Chennai Entrepreneurs taking the world by storm makes for an inspiring story.If you like to travel you must read this post and plan your next international holiday quickly.

If you love entrepreneurship stories, you will love listening to the podcast. On my Blog today and on the podcast, Hari Ganapathy co-founder of Pickyourtrail.com trendsetting travel tech startup.


Tell me a little about Pickyourtrail. What is it?

Pickyourtrail is a travel-tech company based in Chennai that is changing the way Indians travel abroad. Pickyourtrail began as an attempt to break how vacations are being planned and booked by travelers. At its very heart, we want to create happiness, not sell a package. Travel is an experience and we wanted to re-create that magic while putting a trip together. That became possible with our unique personalization algorithm. Pair this with our ability to find best online prices and you have a hassle-free and easy-to-use vacation platform!

What made you decide on a custom international experience?

Srinath & I were motivated by our quest to give Indian travelers to experience destinations at a leisurely pace rather than as cumbersome and restrictive packaged tours. That’s how it all began.

What are the destinations you are offering?

Across the globe.160 cities world over.

Vacations across the Globe:Destination Collage

What should be the average budget for a pickyourtrail family holiday package?

It depends. That is the deal with Pickyourtrail. We believe the best holidays are the ones that you plan from scratch. The price again depends on the destination, the activities you choose, the season, and the availability. So, there is no fixated average budget for a family holiday as such.

Do the prices change after it is booked?

Once booking is done, the price sticks and no change occurs. Every six hours the costs of flights and hotels are updated automatically.

Who are the people behind this venture?

Pickyourtrail was completely bootstrapped with a seed capital of less than a Lakh and it remains the same even now. As a bootstrapped startup, unit-economics is key especially as you scale. Otherwise, you can suddenly find yourself cash-strapped in an Augenblick. Our focus on cracking unit-economics early on has augured well for us even as we have scaled. Currently, we are a strong 75+ team and growing.  

Image credit: Pickyourtrail team-pickyourtrail

Image credit: Pickyourtrail team-pickyourtrail

How was the idea conceived?

Be it the biggies in India or world-over. Everyone still sells packages. Indian travelers continue to be exposed to packaged, run-of-the-mill travel experiences. Aren’t you tired of waiting for agent quotes, or putting your vacation plan together in an excel? This was the problem we set out to solve and it has not been easy to crack. We wanted to make vacation planning fun. Help you discover the best possible price, suggest unique activities that will suit your taste and provide real-time support which will elevate your in-trip experience. Most importantly, we wanted to make vacation planning and booking a delightful experience. And this is how Pickyourtrail was born.

Tell us the 5 steps to start your own business in India.

Have a north star for yourself. A guiding light on why you are doing what you are doing. Me and Sri were quite clear that we are here to build a consumer brand and not a tech startup that would flip/sell in “x” years. You would be surprised the amount of stability it gives you as you try and build your startup. There is no right or wrong, but having that clarity is important. It changes your perspective, time horizons, and metrics that you would measure your startup’s success with.

While it’s easier said than done, have a life outside of work. It could be a hobby, it could a reading club, traveling :), or even kids. But that balance helps you work better. I know it might sound counterintuitive, but some of our best ideas have come in our switch-off modes! And most importantly, enjoy the experience. If done well, it’s the best learning curve for your individual.

Women at pickyourtrail.com:Image credit pickyourtrail

What is your biggest challenge now?

We have grown ~100% year on year from the time of inception. And all of this has been at the back of amazing customer love and support. Right now we are at a stage where we believe that the tailwind is strongly behind us and we are set for an even faster growth. Having said this, history is filled with examples of companies that lost their plot after reaching great traction. We are extremely cautious as we try and balance the scale and standardization game. We cannot ever put our customer happiness on the back burner. In fact, one of the key levers for our growth is unprecedented leaps in customer delight.

If I want to book my international holiday next year in June, when should I start planning?

Ideally, you have to start planning your vacation 6-7 months prior. So, if you want to go on an international holiday next year in June, you have to start planning by December.

Your recommendation for the first international family trip.

While the best destination to visit is heavily dependent on the season, I’d recommend Europe and ANZ as they offer a wide range of things to do which will suit any age.

HOLIDAY with pickyourtrail

Tips for startups:

  • Translating the vision or idea to product.
  • How to collaborate with talented people and retain this driven workforce
  • Understanding the business. Pricing should be relevant and be profitable.

Super tip if you are planning an International trip 

  • For Southeast Asia preplan by three months.
  • For Europe and USA, six months is pre-planning

 List of services that pickyourtrail.com offers
  • Customizable itineraries
  • Live prices for everything from flights, hotels to activities
  • Live travel concierge
  • End to end booking through our platform
  • In-depth destination knowledge with Pickyourtrail’s Guide

Head to pickyourtrail.com to plan your next travel destination.

If you have a startup and want to share your story don’t forget to subscribe to my blog and email me at dramrita@healthwealthbridge.com with all the details.I promise I will get back.


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By Dr.Amrita Basu(MBBS,MS)

I am an ENT surgeon by profession, previously working at a Medical college. I believe the Internet is God's way of providing health and wealth information for all. The important thing is to find the right information.

11 comments

  1. Travel is truly an.experience and not just a package. Love the idea of live prices and a detailed guide. Helps so much in deciding the experience!

  2. The thoughts behind the creation of this brand is mind blowing. Add to that the perks a customer can enjoy, customizing your trips is something we hadn’t heard of in travel biz before. As a potential client they have already won me.

  3. Who gives a better offer than this. To be able to personalize our trip sounds so exciting.

  4. i love the whole idea behind this start up, and i am going to recommend this to my husband. we have been planning our first international trip since long.

  5. I love the concept/idea behind pickyourtrail. Podcast is fab too. I will ask my sister to check their website as she is planning to visit me in the UK but wants a proper European trip. She might find a good deal.

  6. To be able to personalize the trip with no changes in price after booking is something I loved it. Its a great support that they are available over 160 countries globally. We are a travel family and would for sure try their services.

  7. Sounds like a great concept to be able to personalize exactly the type of trip you want to take instead of a canned package for the masses.

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