13 Reasons Why You SHOULD NOT Go On Your First Anywhr Trip

You may have seen photos, videos even, of your friends opening that brown envelope from Anywhr at the airport for their short weekend getaway or exotic destinations off the beaten track. You might have been one of those who have placed bets on where that friend would end up going, and scrolled through their social media updates as they navigated their way around the newfound destination. You might have even kept checking your calendar to find the next best time to book your very own Anywhr trip.

Or maybe not. How is bespoke travel even a thing? How do you even prepare for such a trip that’s personalised for you, yet to somewhere less-travelled? Think no further, here are thirteen reasons why you SHOULD NOT go on your first Anywhr trip.

1. You don’t know where you’re going

I mean, who wants that, really? As if travelling itself isn’t unpredictable enough, you now have to deal with not knowing where you’re going? No, thank you. I can plan my own trips based on the typical travel websites or copying the whole itinerary of that lifestyle influencer I stalk.

Not knowing where you will be going is an adventure itself! A short 1 week trip with lots of exciting stories to tell :) - Joyce
Not knowing where you will be going is an adventure itself! A short 1 week trip with lots of exciting stories to tell.
— Joyce

2. You’d face the unexpected

With no idea what to expect, because sometimes you don’t even know your destination existed before your trip, there’s so much uncertainty ahead when you could have just planned your own trip down to the very exact minute. By doing that, you can know everything you will be doing and everywhere you will be going, even before you leave your house! That way, maybe you can even save your money by simply planning every detail and looking at pictures online but not book your tickets, since you already know everything to expect during your trip.

However, going Anywhr forces you to embrace the unexpected. From making new friends in the least expected situations, to finding hidden spots that even locals have no clue about - every new day is a great question mark of what you will discover.

3. Comfort zones don’t exist

You thought resisting opening your Anywhr Mail the week before your holiday was the hard bit? How about arriving at your destination and discovering that a scenic mountain hike awaits the not-so-outdoorsy you? Or trying out a totally new activity, instead of your usual shopping and cafe hopping during your holidays?

Anywhr Surprise Trip Bad Reviews Blog Arif
I will always remember the scenery. I would never have done it on my own. I will normally go to places that are safer, like shopping malls, or get people to drive me to places to sightsee. This has been my greatest achievement!
— Arif

4. You’ll meet only locals

Anywhr promises to send you to off-the-beaten-path locations according to your preferences, which can only mean one thing – you’re likely to be the only or one of the few foreigners at that destination. A truly local experience - I really don’t see how this could be a good thing? Especially when they host us with a traditional high tea unique to that part of Europe, when all I want is a Milo Dinosaur. Ugh.

Anywhr Honeymoon Samuel Esther Surprise Holiday Review Blog
Special shoutout to our host’s parents! They were so hospitable, and took us on a verbal tour over high tea at their place!
— Esther & Samuel on their Honeymoon
Source: Belinda, Anywhr Traveller

Source: Belinda, Anywhr Traveller

New destination, culture and cuisine. It’ll be so different from what you’ve ever imagined that you’ll probably find yourself too overwhelmed at the start. I’m not sure if leaving our comfy offices and convenient MRT system for a brand new experience sounds like something we’re all game for, right?

6. Incessant questions from friends about your trip

Friends will keep asking you where you’re going with Anywhr because they can’t believe such a cool new way of travel actually exists and isn’t a scam. How will you enjoy your holiday if you keep having to update your friends about it? From how it works to where you’re going and whether you’re still alive, the questions keep coming before, during, and after your trip. Anywhr travellers are the legit influencers, we say.

7. You might lose said friends

Source: Afiqah

Source: Afiqah

To get around updating your friends, you decide to capture moments from your trip on social media with the Instagram hashtag #GOANYWHR, much to the annoyance of your friends as their feed fills up with amazing photos of your newfound destination. Imagine being stuck in yet another Monday morning meeting at work, while you see your friend flinging that little red Travelogue around on their Instagram stories. Ouch.

*Related Post: 5 Guilt Free Reasons to Share your Travel Experiences on Social Media

8. Non-stop discovery

Just when you think the excitement ended with the revelation of your destination, wait till you flip through the pages of your Anywhr Travelogue, peppered with missions that you can attempt during your trip that is both thrilling and challenging, like locating a secret beach. I don’t know about you, but that seems way too tiring for me. I’d rather just stay in my comfy hotel room watching Netflix.

9. Nothing else will excite you anymore

Once you’re back, you’ll find yourself searching for air tickets to your next destination. But you’ll hit a dead-end because you realise that the best part of your trip was going to somewhere you had no idea about, because you had zero expectations and full-on anticipation. You start to question how you’ll ever travel normally ever again. Or maybe, is Anywhere the new Somewhere?

10. Everywhere your friends suggest from now will seem too mainstream

Source: Unsplash

Source: Unsplash

Instead of the usual locations like Bali and Phuket, you wonder if there’s a secret unexplored island nearby instead and find yourself staring at the respective countries’ maps, determined to find somewhere off the beaten track or whose destination name you can barely pronounce. Perhaps, you might even catch yourself trying to discover hidden gems back in your own home country! It's a movement, after all.

11. It will become an addiction

Source: Janene

Source: Janene

You’ll soon realise that the rush of adrenaline you feel when you open that Anywhr mail will become a feeling you want to relive over and over. Or as our traveller Eddie said, "It's chronic OMG".

12. You will get lazy

Once you’ve realised you can have a fulfilling holiday with zero pre-trip research, you’ll slowly find yourself omitting this step on your future holidays, convinced you’ll make it work somehow, much to the chagrin of your travel companions who just think you’re being lazy.

*Related Post: Destination X – On finding fresh perspectives from the unknown

13. It changes your entire mindset about travelling

Once you’ve gone on your first Anywhr trip, you’ll never be able to travel in the same way ever, whether it’s being more open, adaptable or just more curious about anything and everything. In fact, your friends might start to think you’re weird for skipping past all that planning, for being a tad too spontaneous, and for being way too chill about missing the train to your next destination. But you shrug, because you know there isn’t anything that you can’t handle once you’ve conquered your first Anywhr trip into the unknown.

Anywhr Family Xinlei Surprise Trip Holiday Review Blog
My family explored more places than what was mentioned (in the Travelogue) and met more people than we expected. It was a good bonding trip for my family and it was a destination that we would not have thought of going if not for your team.
— Keng Min

If you’re still unconvinced on why you shouldn’t take that first trip with Anywhr, or think that these aren’t compelling-enough reasons to deter you from taking that plunge, then I guess the best way to find out would be to dive right in here.


A former communications professional taking a break from the 9-5 life to travel the world at her own pace. While she's not out there seeking new hiking spots, she can be found working out at the barre (and perhaps occasionally also at the bar).

A former communications professional taking a break from the 9-5 life to travel the world at her own pace. While she's not out there seeking new hiking spots, she can be found working out at the barre (and perhaps occasionally also at the bar).