“You don’t know where you’re staying? Or the time of your flight? You don’t even know what currency you need to bring!”

When I told family and friends that I booked a surprise trip with local travel start-up Anywhr, I got a mixed bag of responses. One group was incredulous and convinced I could be getting scammed. Others were tentative and encouraged me to be #YOLO. My mother, utterly perplexed, asked: “Why on earth do you want to pay for a trip and not know where you’re going?”

So here’s the thing: I paid precisely because I didn’t want to know where I was going. Perhaps I was getting travel fatigue in planning detailed travel itineraries. I’m also a bit of a lazy traveller in that I love the spontaneity of discovering new things on the spur of the moment. The thought of trawling through websites to look up flights, hotels, and things to do seemed to suck the fun out of a holiday. So this time, I was determined that things would be different.


Is this what #wanderlust really means?

Image: Anywhr


So when I came across Anywhr, a company that promises to surprise you with a flight to a mystery destination plus get the accommodation sorted, I was intrigued. Somehow, I managed to persuade a friend as gung-ho as I am to join me. There are three types of holidays you can choose from: Experience (living like a local), Adventure (hitting the great outdoors) and Getaway (relaxing by the beach). There are also three different price tags for each category, depending on whether you want to go budget, regular, or luxury. Prices start from $300 and also escalate according to how long you want to travel for. We picked Adventure for a four-day trip on a regular budget, which cost us $700 each.  

During the booking process, we filled out forms stating the countries we have been to and our travel preferences. We didn’t have any special requests, but this would be the time to share if you have dietary restrictions or can’t swim, or essentially any information that would come in handy.


Three days later we received a teaser email. Knowing the weather was a big help, and given that it was just a short trip, we were fairly certain that we would be travelling within Southeast Asia. That didn’t dim our excitement, and up till the night before we were excitedly trading guesses of where they would send us.

I loved the liberation of not knowing where I was going, and how light I was able to pack. Ordinarily, I would think of all the different scenarios I would be in and which outfit to wear. Having a complete blank slate meant I was stripping it down to the bare essentials: comfortable T shirts, leggings, sports shoes and a backpack.   

The week before the trip, Anywhr sent us an envelope. A message was scrawled at the back of it, telling us to open it only at the airport. I buried it in my drawer and resolved not to succumb to the temptation to rip it apart.


Getting away, getting excited


On the day of our flight, we tore open the envelope to find postcards, a travelogue, and a card that announced we would be going to Yogyakarta in Indonesia. At first, I was a little disappointed. Anywhr promised to send us to a lesser-known area, and Yogyakarta (or Jogja) was famous for being the home of Burobudur temple, a heavily-frequented tourist spot. However, flipping through the travelogue, we realised that on the list of recommended activities, there wasn’t a single temple in sight. Instead, they suggested hikes, visiting waterfalls and caving, activities I didn’t even know existed in Jogja. It was just the off-the- beaten-track element I was looking for.

The travelogue also gave us practical information: a map and contact numbers of the hosts for our homestay, details of where to find money changers, emergency numbers for the police, ambulance, and Singapore embassy in Jakarta, and the contact details for the Anywhr team. The latter would prove handy when there was an accommodation mix-up and our hosts forgot we were coming. The team called them, and it was quickly resolved. We weren’t going to be homeless.


Jomblang Cave, Yogyakarta

Travelling to Jogja turned out to be one of the best holidays I’ve had, but honestly, that was mostly down to our own resourcefulness. It was up to us to find a great guide, to ask around (both locals and fellow travellers) where the best places to eat and visit were, and our willingness to try activities like abseiling down 60 metres into a cave. That being said, I would give the Anywhr team credit for picking a location that met our brief of wanting an outdoor adventure, and creating an environment that forced us to think on our feet and be more spontaneous. The travelogue also pointed us to some great attractions, like the Jomblang Cave which became one of the highlights of our trip.


So here’s what you’re paying for

Image: Anywhr


After our trip, I contacted Zelia Leong, one of the co-founders of Anywhr, to do a breakdown of what you’re paying for:

– Obviously, flights and accommodation. Zelia, who previously worked in the hotel and hospitality industry, shared that they have exclusive deals with travel partners to keep the prices as low as possible. These partners also share details on recommended accommodation, the current weather situation, and how safe the city is at the moment.  

– The surprise element. Basically, you’re trusting professionals to look at your preferences, consult their partners and decide on a place that they feel works best. Want to have a beach holiday but can’t swim and don’t eat seafood (yes, this was an actual request)? You’re paying a travel matchmaker to deliver.

– A personalised travelogue. If you’ve stated in your form that you require halal food, the Anywhr team will speak to locals to share suitable haunts and include them in your travelogue.

– A get out of jail card. Sometimes unforeseen circumstances happen, such as missing a connection due to a delay on the previous flight. If you give them a call (Zelia says her phone rings at all hours), it’s on them to fix the problem and cover the additional cost. That being said, if you woke up late and missed your flight, then you’re footing that bill.

– Transfers from the airport and drivers are typically not included. However there are exceptions – if your destination is extremely secluded, or if people in your traveling party need assistance (families with babies are an example).

And if you’re still worried about scams, it might assure you that the company is recently licensed with the Singapore Tourism Board.


Most importantly, is it worth it?

Timang Beach, Yogyakarta


Well, a lot of what you’ll be paying for are intangible benefits, such as trusting the company to find a great spot to visit and finding a hotel or hostel that you’re comfortable with. I would say it boils down to the kind of traveller you are. If you like to maximise your money and time by ensuring you’ve visited all the attractions the destination has to offer, or if you’re particular about where you stay, then this isn’t the concept for you. Or if you want to relax and have everything taken care for you, again, this isn’t the way to go. Anywhr does settle the hassle for you pre-trip, but once you land, you’re on your own.

But if you’re looking for a novel experience and want to leave all preconceptions, preparation and worries at the door, then I say, get surprised. It’s not the kind of trip that strives for perfection, but it does leave plenty of room for discovery.

For more information, visit www.anywhr.co/