Epic Side Trips | Cape Town

Blessing the winds down in South Africa

Michael Constable
Future Travel
7 min readJan 4, 2018

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Often times on Remote Year, you end up signing up for events and side trips that you never really intended on doing solely because the thought of missing out is too unbearable due to everyone else’s enthusiasm about it.

That’s pretty much exactly what happened to me back in Month 4 when I signed up for a two week side trip to Cape Town in between Months 8 and 9. I had never planned on Cape Town being somewhere I’d go this year, but there was a trip happening, I was invited, and everyone seemed really excited about it.

FOMO didn’t completely drive this decision, however, as I felt pretty good that it would be, at worst, an above average time because everyone and their sister — my own included — raved about the place and the group that was going was a group of people I hadn’t spent much quality time with (and largely still hadn’t by the time of the trip).

Over the course of the months in between booking and tripping, my philosophy on balancing time in our home city vs. side tripping started to shift, and it made me nervous that I had bitten off more than I could — or wanted — to chew.

I started to value chill, quality time in our home base cities over doing multiple side trips, and I also valued waiting until you get to a city before you start planning trips from it.

After all, two weeks was the same amount of time I had spent in certain cities that were actually on our itinerary, and I was afraid I was short-changing KL by leaving so early, too.

Clearly, this exorbitant two week trip that was booked five months in advance ran counter to both pillars of my new philosophy.

All that being said…

Often times on Remote Year, you end up signing up for events and side trips that you never really intended on doing and they end up being some of the best fking times you have throughout the entire year.

That was Cape Town for me.

The Krew

Cape Town itself is amazing, but the group of people that went on the trip are what really make this trip stand out to me now that I’m a few weeks removed from it.

I was initially excited about this trip way back when because I had not spent a lot of quality time with the people going, and it’s on these types of trips where some of the best bonding happens. Cape Town was no exception.

It was a good reminder that no matter where you are in the year, Month 1 or Month 9, it’s never too late to seek out new friendships within the group and put in the effort to get to know someone a little bit better.

Cape Town

Cape Town is one of the most naturally beautiful (and windiest) cities I’ve been to this year. From the gorgeous beaches that were lousy with the vibrant kites of the people surfing from them, to the mind blowing views of Table Mountain from every angle in the city, to the epic sunsets every single night, I was constantly having to wipe the dumb smile from my face and the drool from my chin as I’d go full on drool emoji mode from staring at something in wonderment for too long 🤤.

This was my second time to Africa this year (wut), but the two trips could not have been any more different. In Morocco, I was constantly feeling anywhere from a little to a lot on edge while I adjusted to the raw, intense chaos that was going on around me most of the time. In Cape Town, things were much more modern and comfortable and familiar. I can see why RY chooses to go to both Marrakech and Cape Town because they are two completely different worlds.

Highlights:

  • Waking up in the kind of Airbnb that makes you never want to leave your house, having Matt DePaso walk downstairs bellowing “GOOD MORNING, GOOD SIR!” in what I think was a British accent, and him proceeding to cook Liz and myself two course breakfasts from scratch every single morning.
  • Spending an afternoon in Betty’s Bay with Leandra’s family while they showed us a proper South African braai, which is their version of barbecue. Oh, btw, her aunt and uncle are so good at it that they were on a South African braai masters TV competition.
  • Winery hopping around Stellenbosch.
  • Going to see Mi Casa play at the Kirstenbosch Gardens, which is easily the most incredible amphitheater I’ve ever seen. Mi Casa was actually surprisingly excellent, too. I say surprisingly because I had never heard of them, but they were really popular to the locals.
  • SHARK CAGE DIVING (!!) off the coast of Gansbaai. Apparently Orcas are casually killing a bunch of Great Whites in the area, so we didn’t get a chance to see any up close, but we did see a bunch of Copper Sharks that seemed plenty terrifying in their own right.
  • Hiking Lion’s Head just in time for golden hour and sunset.
  • Driving five hours to do a two day safari at Botlierskop. We were able to go on two game drives, see four of the big five (aka the most dangerous), witness the most adorable newborn zebra struggle to stay upright, WALK WITH LIONS, and get a little bougie at the spa. This included an introduction to the bougiest and fiercest lion in existence, Spinecoat, who literally wears the spine of her kill like Cruella DeVille wears her dog coats. Chick is dripping in both decadence and the blood of her enemies.
@spinecoat 💅

This will go down as one of my favorite side trips of the year for many reasons, which is why it warranted its own post. Well, that and the fact that I spent as much time in Cape Town as I did in Sofia, KL, and Lima — three cities that are actually on our itinerary.

Whoops.

I have longterm plans to come back with Jen(Cho!) and take kite surfing lessons because the kite surfers were extremely badass.

Thanks to Cape Town being Remote Year’s newest city, the odds of that happening are looking pretty good right about now 😉.

Photo credit + a yuuuuge thank you to Liz and Matt for taking such great pictures and for putting up with me pestering them for a month to get my hands on them. ❤️

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