I'm nearing the completion of my 8th trip to Cape Town. It was the most visited International City (excluding family spots like Mumbai & Bangalore, and London which is influenced by going for work a bunch) when I came here for the 5th time, but now it has a pretty wide lead. Unlike basically all my prior trips, I didn't/have not done a day-by-day diary of the trip. Not sure why, but thinking about it, writing about quite a few same restaurants, sites, bars, etc., would be a bit boring for all involved. Granted, there were some new things. Instead, I decided to take this trip to think a bit more holistically - so I have two pieces planned. First is this one that ranks all eight of my trips. The second will give some thoughts of how the city has changed over these 12 years - mostly for the better, but some ways for the worse (or at least changed in a sad way).
There's no formulaic approach to this ranking. It's mostly just looking back at how fun, notable and meaningful each trip was. All eight were good, by the way, but there are definitely differences here.
Lodging: Hostel (The Sunflower Spot)
Notable Firsts: Kirstenbosch, Signal Hill
The main issue with this one was it was too short. It was squeezed onto the end of a trip to India for Christmas, and I spent 1.5 days in Johannesburg first. I really wanted to visit again after my first trip, bt really didn't plan all that much. I stayed in a hostel (admittedly, a better one than the one I stayed at in 2013), and really didn't venture out too much. I honestly have no specific memory of this trip in terms of doing things for the first time other than (1) first time visiting Kirstenbosch, probably the biggest "gap" from my first trip, (2) visiting Camps Bay for dinner one night (which was excellent) and (3) going to Signal Hill for the first time. Other than these two things, a pretty forgettable trip, which makes it more ironic I wanted to so quickly return.
7.) 2024 (February, 5 days)
Lodging: AirBNB on Vesperdene
Notable Firsts: Salon, La Colombe
This is the only trip where I ever thought to myself "maybe I come here too much". Now, it was still a great trip, but there were a few things that drag it down. First, one day had a decent amount of rain, which is probably the only day in all my trips to Cape Town where this was the case. I was able to escape it indoors for a good amount, but still that was a damper. Secondly, this was a time where I was still trying to hold onto some old things - like a last trip to The Waiting Room, which it along with a lot of Long Street, went way down in the six years (I say this because get ready to hear a lot about it in the 2018 version). The only "new" things I can point to are probably meals at Salon, which was amazing, and La Colombe, which was excellent but also way too far away for it to really be worth it. Maybe the only other notable positive was rediscovering Mitchell's - a bit by mistake as it was the only place open when I reached the Waterfront around 10:30 on Sunday - that being such a quiet day I've now just decided to switch days in my trip and avoid being here for Sunday nights. Also, more so than prior trips, I was impacted by load shedding - mostly when I had to walk up to the 5th floor when returning to my AirBNB at 3am. Look, I've done a lot of complaining, but it was still a great trip (and the end of a great overall trip that included Turkey), and more than anything I think I learned a lot from this trip in terms of changing it going forward, which led to a better one in 2025.
6.) 2025 (October, 4.5 days)
Lodging: AirBNB on Vesperdene Road
Notable Firsts: Fyn, Talking to Strangers, Fable
Notable Firsts: Fyn, Talking to Strangers, Fable
It's funny that in theory my 2nd least favorite and 3rd least favorite are teh last two trips. I will say, there is a big gap between my #7 and this trip here, and also there are all specific reasons why each one ahead of it ranked above. But in terms of just playing the hits, I don't think I've had a better trip. That extra 6 months in between visits (after spending basically three straight President's Day Weekends here from 2022-2024) made me miss it so much. The weather was incredible (save for ironically the day I went up Table Mountain, which had its normal rolling clouds stuff going on). The hikes were brilliant. I forgot how good the foliage is in Spring, with a stunning visit to Kirstenbosch. Also, leaving Sunday Night instead of Monday night was probably a good trade. I tried some new places - from Fyn as a brilliant tasting menu spot, to more importantly expanding more into the getting more built-up Waterkant/Downtown area, with cocktail bars like Talking to Strangers and Fable. We've seen that transformation - of things moving away from Long Street and the Waterfront (Cause Effect plays into this - still great but no longer the only option for great cocktails) and to this new area that if anything makes Cape Town more full. What I learned on this trip is October is arguably the best time to visit (even if four of the five trips above it are in February), and Cape Town may always hold onto its charms despite growing in stature every time.
5.) 2013 (February, 4.5 days)
Lodging: Hostel (Altona Lodge)
Notable Firsts: Everything I did (main ones being Cape of Good Hope, Stellenbosch, Table Mountain, the V&A Waterfront)
The first trip ranks lower than I would've predicted. Two aspects are important in that fact - firstly, I've just had a lot of amazing trips to Cape Town. Secondly, so little of this trip resembles anything of trips thereafter. I stayed in a hostel. I stayed mostly in The Waterfront area, aside one night venturing to Long Street. There were no clubs, no cocktails - granted, a lot of Milk & Honey beers at Mitchell's. It was by far the most "touristy" trip of any I've done, but this is not a negative. I can still remember that day doing the Cape of Good Hope tour, and even what is still my only trip to Stellenbosch (which is stupid on my part). It was my first trip up Table Mountain. Of course, this trip to Cape Town came as the first stop on my Round the World trip, which changed me as a person, and I think the fact that Cape Town was an incredible first dish on that trip is a big reason for it.
This was by far the most limited trip food-wise, but weirdly still memorable. At the top of those memories is City Grill, an African BBQ/Steak place taht still holds its busy place in the Waterfront - where I went back to back nights, to where they gave me a free bottle of wine the second night. That sauce for the Crocodile dish is still seared in my brain. As were Fork and breakfasts at Vevo Telo and what not. It was also the most docile trip - I think I got drunk, in the technical sense, maybe once (of course, overdid it to where I drank tap water in my hostel room to sober up... which got me sick...). I look back at photos of this trump and just smile - it was a simpler time, simpler for me and the city. I've seen the city grow up in a way, and in a way that aligned with how I did. As a first trip, it set a good standard that I'm happy to say has been topped half the time.
4.) 2020 (February, 4.5 days)
Lodging: AirBNB on Dock Road
Notable Firsts: Belly of the Beast, Reset, Cause Effect
There's a great irony in this trip in that it was a great reset into how I operate in Cape Town. There might not be a more "important" trip in that sense, but it is also the one that I left my phone in an uber going to Kirstenbosch, so I have very few photographic memories of the trip. But, a quick list of things I did for the first time that would become recurring trends thereafter: first time I visited where Cause Effect was open, cementing its place from Mitchell's as my go-to Waterfront haunt. This was also Cause Effect at its most popular, inventive, and acclaimed. It was the first time I did a tasting menu (excluding Janse & Co), going to Belly of the Beast. It was the start of the move away from Long Street - The Waiting Room still decent at this point, but Fiction closed and the rest becoming too R&B. But in it I discovered Reset, which was an amazing EDM club that was before its time (in location, as has been reborn as a way worse velvet-rope place and there are now bars all around it). Reset was truly amazing. I'm also not really considering the flight to and fro as part of this, but it was the first time I ever took Polaris, and the first time after United starter their direct EWR-CPT flight.
There's also an important "last" in this trip - as it was the last time I went to The Dubliner, such a key part of early trips. It was Sunday Night, looking for a place to go out late (a common challenge on Sundays) but around midnight, at The Dub, there was a guy with a guitar taking requests and playing great Rock music. There was a group of German tourists already there that I got started talking to, and we ended up having an amazing night. It was the capper to the trip, and of course it was a month before the World would go quiet for a while. Already at this point in Feb there were signs around people should not go if they were sick and what-not. It definitely felt like taking a trip while the Titanic was sinking. Honestly, had I not lost my phone and had more physical memories of the trip, it may rank higher. I should say, the losing my phone detriment is just the fact of losing pictures. The actual losing of the phone is my fault alone and not any fault of Cape Town.
3.) 2023 (February, 5.5 days)
Lodging: AirBNB on Vesperdene Road
Notable Firsts: The towns on the Cape of Good Hope tour, Gold
I will say, this is the trip I took with my parents, and getting them to visit Cape Town, and seemingly love it as much as I do, matters a good deal. If this trip was alone, it probably ranks below 2020, and maybe below 2013. I still have a giant smile on my face when I see pictures of this trip of my Mom and Dad experiencing the Waterfront for the first time (on their Anniversary, no less), Table Mountain, Penguins and so much more. It was the longest trip arguably, and probably the most packed. It was, in ways, a perfect blend of 2013 (tourism focused) and 2020 (food, nightlife, vibes focused) - as I did a Cape of Good Hope tour, which was better this time as it was private and included stops at some adorable towns. It was also just the third time I did Table Mountain, which I promised myself that day I would never miss on a trip again. I also blended in hikes when my parents were off doing touristy stuff I didn't want to redo (e.g. Stellenbosch), but also included the most extensive visit to Kirstenbosch yet. The 2020 elements were the nights at Cause Effect, House of Machines, Modular and more - and some incredible meals.
I don';t know if there was a trip I ate better on (other than arguably 2025). We went to Pier that first night (parent's anniversary), but also took them to Belly of the Beast, Pot Luck Club, and more. The only sad part was this was after the V&A Food Market closed (and before it reopened as a fairly soulless TimeOut Market). Another notable part of this trip was staying on Vesperdene Road for the first time, which is a perfect location and is basically my go-to for any future trip to Cape Town. It is 15 minutes to teh Waterfront, two minutes to Woolworths (for sundries), and has some great AirBNBs/apartments. As noted above, other than some new parts of a tour that repeated 80% of the first Cape Horn tour, and a restaurant which is more about culture than teh food necessarily (Gold), I didn't really do anything new on this trip. But, at the end of the day, though, sharing a place you love like Cape Town, with people you love, it gets some extra points. In that vein, I can virtually guarantee that if I am lucky enough to get married one day, the first time i visit Cape Town with my wife, it will likely rank this high if not higher.
2.) 2018 (October, 5.5 days)
Lodging: Protea Hotel in Green Point
Notable Firsts: Long Street (The Waiting Room, Fiction), Modular, The Pot Luck Club, Miller's Thumb, Janse & Co, The Pipe Track, The Contour Path
As that lengthy list of firsts makes it clear, this was a damn eventful trip. And it doesn't even include the first of it being the first I would be with someone, as my friend joined me for the trip. This was a seminal trip to Cape Town in many ways. The first is it was where I first did hikes on the larger rock formation that is Table Mountain - from The Pipe Track (which might be my favorite trail in the world), to the Contour Path (with me learning it is a free way to see Kirstenbosch), to even Maclear's Beacon on top of Table Mountain, this trip was a hiker's paradise. It was also the first time that I didn't stay in a hostel, and while I haven't stayed in a hotel since (all AirBNBs), that itself was a huge upgrade. But most importantly, and why this ranks so highly, is this is the first time I really "lived" in Cape Town.
Other than the trip to come, no trip had better vibes than this one. Cape Town nightlife is great, and while it has changed a bit over the years in location, this was peak Long Street. You had the R&B bars you still ahve today, but you also had the center of the city's EDM/Techno/Rap scene. I can still remember those nights ping-pong-ing back and forth between The Waiting Room and Fiction - the former being "hipper", the latter being at the time the city's main EDM house. Best were both were 2nd floors on Long Street with outdoor balcony areas. Sipping on a drink, with the music thumping on the other side of the doors, looking down at Long Street below - that was an amazing moment. The food also changed on this one - probably from my first trip to Janse & Co (RIP) which had a great "pick 7 of 15 dishes" version of a tasting menu, that I still miss to this day. Cape Town was starting to grow as a city, just as I was as a person, but this caught both things at their inflection point - I wanted the lowbrow fun of The Dubliner and Mitchell's and Miller's Thumb, with the highbrow aspects of The Pot Luck Club, Janse & Co, and in 2018, all of it was readily available. If not for one Covid-related aspect of the #1 trip, this is about as good as it would get.
1.) 2022 (February, 4.5 days)
Lodging: AirBNB at the Docklands
Notable Firsts: Modular (in reality), Pier, Between Us, World of Bids
I'm not going to lie, a large part of this ranking is the fact that it came right as Covid ended. In fact, I was concerned the trip wouldn't happen, as the infamous Omicron variant started in South Africa the prior October. But by February it had washed through both South Africa and the US, and this trip was meaningful in a "the world is open again" way as much as it being an amazing trip. I returned to a changed Cape Town - Long Street less important, Reset dead, Modular alive, but the same foundational elements were still super strong, if anything, it was the start of its rebirth, with it becoming more and more modernized (read: Western) - my other piece details the mostly positive results of that shift, but it is unmistakable - from the buildout of the CBD, to more clean, corporate elements of The Waterfront - seemingly Cape Town became more "mature" post Covid.
As I mentioned earlier, my flights aren't really a part of this consideration, but one moment is - my view as the plane's landing took us across the Bay, with a perfect, truly "birds eye" view of Cape Town in all its glory - it was the brilliant end to a great flight in Polaris, and the start of a new era of travel really. The trip itself also had some notable elements - with my first time trying a super fancy (for Cape Town) tasting menu in Pier, which was awesome. It also included my first (and so far only) trip to the Bird Park that sits halfway from Cape Town to Camps Bay. It is a lovely place that I ought to return to. Mixing in with all of this was some great nights at Cause Effect (still super busy, before the cocktail spots in center city started expanding), great music at Modular, and more than anything just some sensational vibes. The world was coming out of a two-year malaise (admittedly, I did do a Europe trip with friends in fall of 2021, but that was still a time of mask mandates, and curfews). There was no better place to get out of such a malaise than Cape Town. The trip was so good it basically made me think that I need to go every year.
