I’ve often heard how great Cape Town is. Articles touting Cape Town’s grand appeal as a top travel destination have proliferated on the internet. Numerous friends have gone so far to name it their #1 favourite place. Google images has about a million breathtaking photos of the city, all aerial, all at sunset. So, on a recent trip to South Africa, Cape Town was the grand finale. We spent four weeks driving our way through the stunningly beautiful country and as we inched our way west, my excitement to reach Cape Town rose steadily. My travel expectations were sky high.

At long last we reached Cape Town and we indeed liked it – after that lead up you probably thought I was going to hate all over CT. We enjoyed our time wandering the diverse neighbourhoods, stuffing ourselves with seafood, scoping out the local art scene and sampling Cape Town’s many craft beers and ciders. But it didn’t wow me; I didn’t have this transcendental experience that had seemingly transfixed others. In all fairness though, it was virtually impossible to live up to the out-of-this-world expectations I had.

I did, however, feel the exact opposite about Johannesburg. This landlocked city that never makes it on any top ten list and a place that many visitors skip altogether was where I had my moment. Still as gritty as ever, there was a transformative feeling in the city that was hard to miss, a youthful, creative, and independent vibe that I wasn’t expecting. I loved it. It’s not as though Joburg was necessarily better than Cape Town, it was the weight of expectations that set them apart.

This wasn’t the first time that travel expectations altered perceptions during my trip, in fact I realized it was a fairly common phenomenon across other areas of my life as well. Maybe it’s just me and a curse of my propensity to overthink everything (if you agree – you can leave now), but as I kept coming back to this I started to notice that almost everyone has at least one travel spot that did not live up to their expectations.

Reflecting on my years of travel, I’ve come to realize that my most memorable experiences are those that were spur of the moment or overall under-hyped. There was Leiden in the Netherlands, a university town about an hour south of Amsterdam that was, unbeknownst to us, host to both a music and culinary festival on the sunny June day we visited a few years back.

Overall, I noticed that my expectations were skewing my experiences so I crafted a six step plan to keep my travel expectations in check.


1. Only do the bare minimum of planning.

Plan what you need to make the trip happen comfortably but don’t get bogged down with the details. I call this the art of planning without planning.

Right now I’m planning out my itinerary for an upcoming trip to Iceland. I’m roughing out a basic route and booking accommodations here and there – we’re going on the cusp of peak season and I’m not keen on sleeping in the car because everything’s booked – but I’m not getting into the nitty gritty details like planning daily activities or driving detours as this can inadvertently set off my expectations.

As the trip gets closer, I’ll look into specific things we want to do that would need to be considered in advance, but leave most to be figured out when we’re on the ground. I often begin researching what to do and what to see in a new spot a couple of days before I arrive so I don’t end up missing anything – I just don’t dwell on it for months in advance of my trip.

2. Keep time open to do something random.

If you’re a compulsive planner or traveling during peak season, sometimes you just can’t avoid over planning. If that’s the case, don’t fall into the trap of committing all of your time in advance. I’ve listened at length to friends detail their entire itinerary for upcoming trips down to each meal. I smile and nod but inside I’m cringing a bit. If you plan every moment of your travels you’re not really leaving anything to surprise and are probably building up your expectations to the max based on the research you did to curate this itinerary. Knowing everything in advance kind of takes all the fun out of it.

When visiting a new place, you often get wrapped in the ‘see what you’re supposed to see’ mentality. Set aside time to explore and ask around for tips on what to see and do. There’s really nothing better than receiving firsthand information from locals that would not be on your radar otherwise.

We left ourselves a lot of open time on a trip to Galway a few years ago. Asking around at our B&B and in cafes, we received a wide range of advice on what we should do. Over a pint at a cozy pub, the local bartender enthusiastically suggested driving out to Connemara, the northern area of County Galway. Maybe it was the beer, but he persuaded us. We rarely encountered another vehicle on our ten hour drive through tiny towns, in valleys anchored by mountains, and alongside many, many sheep. It is one of my favourite travel experiences.

3. Incorporate lesser known spots in your itinerary.

If you’re traveling somewhere that you might have built up, like your first trip to Paris or Bali for instance, think about reserving some time to explore less tourist-trodden spots. It could be a neighbourhood, a nearby town, or an adjacent region.

Many years ago when I first traveled to Europe I engaged in the typical Euro trip routine, which involved spending six weeks rapidly moving from capital to capital and seeing nothing in between. There was an exception, though. On our way to Strasbourg about mid-way through our trip, eager to experience the Alsace charm, we stopped over in two small and stunningly quaint towns: Colmar and Selestat. With zero expectations we saw everything through fresh eyes. Our detour to these two towns remains to this day one of the most memorable aspects of that entire trip.

4. Plan with text, not with photos.

I sometimes yearn for those pre-internet days where you would simply consult a trusty guidebook to plan your travels. As you read, the words would jump off the page, conjuring up images in your mind of far away locales. There would usually be a couple of small photos to keep your mind in check, but they would be at a minimum.

Sure, the internet has exponentially expanded the realm of travel possibilities. Destinations are now accessible that would have been virtually impossible before. But with all of this information at your finger tips, it can be easy to find yourself suffering from over-planning paralysis or an inability to make decisions – or both at the same time.

You can’t get away from travel photos entirely, nor should you, but don’t go overboard. Resist the urge to look at a few hundred Google search images before heading off to a new spot. Not only are these unfair photographs – taken from the best vantage points, at sunset, and heavily edited in Lightroom. Leave something to the imagination.

5. Plan the basics, then forget it all.

Plan in advance everything that’s critical – flight, mode of transportation, accommodation, etc – and then put the trip to the back of your mind. Pick it back up again in the days leading up to your travels to ensure you’ve got everything you need, and then spend a bit of time considering the sites, activities, restaurants etc that interest you. By that point your trip is too close for expectations to go on overdrive and, if you’re anything like me, your mind will be almost exclusively focused on trying to get everything done before you leave.

I’ve taken advantage of some great flight deals recently that have required purchase considerably far in advance. Last year, we went to Hong Kong from Toronto for $400 roundtrip but we bought those tickets nine months in advance. We knew we didn’t want to spend the entire three weeks in Hong Kong, so we started researching other nearby destinations and soon chose northern Thailand and a couple of months before we left, we booked flights and lodging. It wasn’t until a few days before we arrived that we actually started to research what we wanted to do in the city.

6. Don’t go solely based on positive hype.

It’s easy to fall under the spell of someone who’s just returned from ‘the best trip of my life’ but don’t hype it up in your own mind by proxy. It’s also hard to ignore the places that seem to blow up in the travel world and become the new ‘it’ destination. But don’t let that be your main reason for heading over.

If you do decide to follow suit, ensure you have your own reasons for going besides one person’s recommendation. And if you’re going to pick a friend/blogger/celebrity’s endorsed destination, ensure your interests, travel styles, and motivations are similar. Your travel expectations are not going to be the same as everyone else’s.

While there’s no problem heading somewhere that gets its fair share of attention, try not to blow up your travel expectations. Keep an open mind and remember the old adage: if it sounds to good to be true, it probably is.

Travel Expectations Photos courtesy of JP Bervoets / Lauren Barth; Departful

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Lauren Barth co-founded Departful in 2012 and is the Managing Director of Departful Media. Since then she has worked between North America and Europe and has published content in partnership with a variety of tourism boards and businesses based around the world. Lauren is currently based in Toronto, Canada.

Departful is a full service travel agency for busy professionals seeking unique and transformative custom travel experiences. We create memorable holidays that are 100% tailored to our clients, saving them time and energy by handling all of the little details while providing value by leverage our expertise and network of travel partners. We are based in Toronto.


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Departful is a full service travel agency for busy professionals seeking unique and transformative custom travel experience. We create memorable holidays that are 100% tailored to our clients, saving them time & energy by handling all of the little details while providing value by leverage our expertise and network of travel partners. We are based in Toronto.

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