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When I told my friends that I had signed up for a mystery 3D2N trip to “I don’t know where yet”, they all thought I was crazy.

I had been wanderlusting for a while, craving for a break in monotony, but the energy required to even make a decision on where to go, book accommodation, and plan a trip just sounded to exhausting. I had put it off for a couple of weeks (annoying my friends and family with my whining in the process), until Harry from Singapore startup Penroads came up to me with an idea that he had been toying with for a new service.

“For S$99/month, we’re thinking of trying a travel subscription service. You get to travel 4 times a year. In other words, every 3 months, we’ll send you on a holiday for 3d2n. Leave Friday evening, come back Sunday night. Flights and accommodation taken care of.”

Two things struck me at the same time. Firstly, how easy this would make weekend trips. I hate planning for trips, and the amount of information you need to dig and scour through has often put me off planning for short trips altogether. I would probably spend around $300 — possibly more if I were really lazy — so this sounded like a real steal.

Secondly, I knew how risky this could be. It was this risk that made my friends furrow their brows at my explanation, and it was this same risk that made my mind race at the possibilities. What kind of accommodation am I going to get? What if they send me somewhere I don’t like? What if my trip goes out of my control?

How It Works

When I raised these concerns to Harry, he had an explanation for everything. They’d only send me to a country within APAC, which works for its 3D2N timeframe, and three weeks before the trip, they’d give me three curated options on cities to visit. If I didn’t like my choices, I’d get an instant refund. Of course, that still didn’t mean that I got to choose the kind of accommodation I preferred, or the airline I’d rather fly with. But on the flipside — I didn’t have to do a thing. That’s freedom.

There’s something about being the first in line. There aren’t any initial standards to base my experience on, or crowd-sourced reviews to mentally prepare myself with. The service, now christened Zenpass, was wholly untested, which made me feel equal parts special and equal parts guinea pig.

So I agreed. I picked my dates, paid for the trip, and waited. I had to fend off questions from friends asking whether I knew where I was going yet, to which I answered truthfully — not at all. Does it make sense that that made me more excited?

Lazy Planner Meets Travel Subscription


Three weeks before my travel date, I received an email. In that email, I was provided with a PDF file with three curated choices — Hong Kong, Bangkok, and Penang. The PDF file also gave a collage of photographs for each city of activities to do and of the accommodation they had already chosen for that option. No name, no explanation on whether it was a hostel, Airbnb, or hotel, though by the bunk beds in one of the pictures, I could sort of guess.

Zenpass Zenpass Zenpass

I decided on Hong Kong — it was a holiday destination that had been on my mind for a while — and I let him know the day after I received the email.

“Okay!” he answered, and then shortly after added: “Was so sure you’d take Bangkok.”

He also shared with me that he originally planned to secure a trip to Yangon for me, as the weather in November is supposed to be great at around 21 degrees. However, the dates I picked clashed with the Myanmar elections, which means there would be a chance of civil unrest during my vacation. I reflected to myself how I probably wouldn’t have bothered doing that sort of background check because I am a terrible and lazy trip planner, and it’s sort of great to have someone else watching my back.

A week before my trip, Zenpass sent a little package with some pictures of food in Hong Kong to entice me, a picture of the Hong Kong MTR map, and print-outs of my flight details and accommodation reservations, along with a little cash to cover the final payment for the hostel I was going to stay in. The hostel was in a great location that was too good to miss out on, Harry explained, but insisted on a cash payment upon arrival. The flight was booked with Jetstar, and was set to leave on Friday afternoon and return Sunday at midnight.

The flight details were also wrong, which I quickly pointed out. Zenpass had that fixed on the spot.



The trip itself was a breeze. The Jetstar flight was as comfortable as you would expect most budget flights to be, and by sheer luck, I was immediately upgraded to a private room with an ensuite bathroom, a definite step up from the 8-a-room female dorm I was previously placed in. I did feel woefully unprepared for my short trip, since I only looked up places and restaurants to visit a few days before my arrival.

I’m already a lazy planner when it comes to travelling, and Zenpass probably made that worse, though I’m not complaining.

Zenpass The Business

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The business model for Zenpass is sort of like the dream of any Singaporean auntie — they earn when they save. Imagine the savings that we attempt to get when we stalk Scoot’s flash sales and spend hours scouring through TripAdvisor looking for the best deals — that is what they earn to support Zenpass. And if they exceed the S$297 mark — then they’re making a loss.

“The amazing thing is that we are currently proffering flights and accommodation options that exceed SGD350 in value while the user only pays SGD297 for three months of subscriptions for their trip,” said Harry. “You would know, your trip to Hong Kong was approximately $360 in value.”

That means that I saved about S$63, while they suffered a S$63 loss. This loss is probably a short-term event; I’d imagine that once Zenpass gathers enough loyal subscribers, it’s possible to leverage on economies of scale to save on their bookings.

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Image Credit: Liang Hwei

So what can S$297 buy you?

Well, it provides us with a sure deal of a little less than $300 for flights and accommodation at any time and to any place. You get a choice of three locations picked for you worth that amount, with flight and accommodation valued at around $300 — on hindsight, Hong Kong was the more expensive of the three options, and I knew right away that I would have to settle for a slightly less attractive accommodation.

It also takes the stress of booking out of my hands, which is a service I would gladly pay for. With Zenpass, however, its practically free.

According to Harry, Zenpass is looking at a $64B market for Southeast Asia’s leisure travel expenditure. Weekend trips is not an unusual occurrence in Singapore, but the time and effort it takes to plan one makes it much more exhausting than it should be. Removing the planning for big-ticket items like flights and accommodation leaves more time for travellers to focus on the trip itself.

Understandably, Zenpass isn’t for everyone. When I spoke to a few of my friends about the experience, even after I had safely and happily returned home, there were still doubts and concerns about the trip. The loss of control to many Singaporeans can be troubling and even stressful, while some hardcore deal-diggers may be adamant that they can beat the $297 price tag.

Signing up for Zenpass, as I did, embodies a different travel philosophy — that the little details don’t matter. Maybe if you took control of your trip, you would end up in a four-star hotel further from Central instead of a hostel, or you could have paid $20 less for a different budget airline. Maybe if you tried, you could dig up a decent package deal from the depths of the Internet. But if you let go of those details, and just focus on exploring a new city and actually unwinding during your vacation, then perhaps that weekend trip that you may have wanted to slave away for could become worth so much more.

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