I've thought about my travels recently. As much as a sports blog, this became a de-facto travel blog a while back. I mean, I still think in pure volume I write about sports more, but ever since my RTW trip, and then love of tasting menus (which coincided nicely at the point where I could afford them), travel writing has been as much a feature.
I wanted to think through which year gave me my best travel experiences. Now, this isn't just about volume of trips, because that has definitely increased the last 3-4 years, cresting with a crazy 2025, an equally crazy 2026 when all said and done. Part of that is again me having more money to spend, but also over-using at this point the company's policy on flying anywhere instaed of home if economically viable - ever since we opened up our Chicago office in 2022, and then had more and more clients requiring some travel, I've tried to maximize weekend trips. But this isn't about just quantity - quality matters here. Some trips are so good they are worth 3-4 trips by themselves. Of course, some of that is just duration.
**One note: I've done quite a few trips that span years (e.g. around Christmas through New Years). For each of these, I am considering the trip solely in the year that started that trip. For instance, in 2017-18 I went to Patagonia - I am considering all of that trip as 2017. Similarly so for The Holy Land trip in 2018-19 (is just 2018), and the South America All Over trip in 2025-26 (2025)**
Tier I - Covid Years...
2020: San Diego, Cape Town, Maine
Look - it was so obviously going to be last. I came back from Cape Town on February 18th, 2020, and then didn't leave the NJ-PA-NY area until September 24th. Where did I go on September 24th? Well, Maine - with friends. That was a fun trip, a rare road trip that I took with my friends (pretty much all of our trips have included flights). Another one with friends was San Diego in January, which was wonderful. Honestly, each of these was great, but it was only three and those seven dark months were damn dark - for travel and for everything else. What really hurts is this was probably the msot forgettable Cape Town trip in a way - though that may be influenced by me losing my phone midway through so the photo memory of the trip is super incomplete. It was my first time flying Polaris (though an older plane) and the Polaris Lounge, so seminal there.
2021 was better than 2020 but marginally. The Arizona trip in April represented my first time taking a flight in 13 months, which is insane given I took about 120 fligths in the preceding 13 months to that. However, some seminal stuff here - this was my first time as an adult to Phoenix, a city I now swear by - that cool air that first night at The Theodore is a damn cool memory. Same is my first time in The Black Box in Denver - to date my #1 EDM club. The Spain & Portugal trip was a wonderful one with friends, finally retracing a bunch of things I did when I was much younger with my family, like seeing the Alhambra with the ability to take it in. Finally, that India trip was a lot of fun as I timed it perfectly just as some Covid restrictions were being lifted - not fully mind you, but at least some potential for nightlife. That said, the Covid restrictions did impact nightlife capital in Spain & Portugal, which was extremely constrained. In the end, traveling during Covid was a relief because it was possible, but still far from ideal.
Tier II - The Pre-Covid Fun...
2019: Bangkok/Gaggan, Italy, Calgary, Taiwan & Vietnam/Laos, Mumbai, Azores
It's weird since as we will get to, in sheer numbers I've traveled more these recent years, but at the time I really thought I milked 2019. That is still the year where I took more flights than any other (121 - v 104 in 2025, 101 in 2024) but I guess a lot of those were just work related. For the actual travels, this was me taking my short trips far away to its natural conclusion - doing the (at the time) longest fligth in the world twice on my trip to Bangkok for four days - which of course doubled as my first time going to Gaggan and probably setting me up for a lifetime of tasting menus trying to chase that high. Calgary was a super fun trip that won't ever get replicated pureley because a couple of my favorite spots there have since closed (Habitat Living Sound mainly - Banff is still very much open...). Azores was forced on me by my sister but was wonderful. But a lot of this is Italy and that Asia trip. Italy was with friends but was probably the least memorable of my friends trips (a bit too staid). The Asia trip however was awesome - my first real time in Vietnam, a great time in Luang Prabang, and those magical few days in Taipei. The only thing keeping it down a bit is the lack of business class flying (yes, I am that vain) and that if anything my experiences in Vietnam have only improved.
2017: San Diego, The Balkans Trip, Nashville, San Francisco, Portland, Patagonia & Santiago
This was a fun year, my first time really taking advantage of the "spend a weekend wherever you want" logic of consulting, as for much of the year, I was flying somewhere - from Toronto at the start, to San Francisco by the end (changed jobs, and obviously then, projects). San Diego was fun as it was my first time in that perfect little spot. Nashville, San Francisco and Portland were all whirlwind of weekends, where I really got my AirBNB love going (I still maintain if you are a solo traveler, a good AirBNB beats a hotel). But this year is defined by those two main trips, both super high up my list of favorite trips period. The Balkans one is probably my favorite trip to date taken with my friends - a perfect confluence of age, ability to live it all out, and see some cool stuff. Finally, the year was capped brilliantly by the Patagonia trip, which probably still remains my favorite single trip I've ever taken - a mysterious brew of brilliant places, great cities, great food, great sights - all of it. Obviously, quantity isn't huge here, but quality so much is.
Tier III - Some Great Years...
2024: Turkey & Cape Town, Santiago, New Orleans, Budapest & Talinn/Helsinki, Denver, Salt Lake City, Las Vegas, India All Over, South Korea + Bangkok/HCMC
Sometimes, quantity just beats out quality - not that the quality was low here, but there's an interesting contrast with the one right ahead of this, which had fewer trips. Anyway, there was a whole lot to love. The only reason this isn't higher isn't a fair one - my one two-week vacation Summer/September trip (something I've done 2018-19 and 2022-26) was traipsing around India - fun but probably the weakest of those specific segment of trips. The time in India was graet but ultimately I fall in teh camp of someone who just doesn't think tourism in India is all that great. Tourism in Istanbul or Cape Town or Budapest or Talinn however? That is great. Those dual one-week (two weekends each) trips in Feb and April were wonderful, as were returns to Salt Lake City, and of course my trip back to Santiago where I really learned to love that city. Finally, with my parents on a cruise during Thanksgiving, it gave me an excuse to book this weird SE Asia + Busan trip which was a bit scattered but ultimately lovely. Actually finally, the New Orleans and Las Vegas were both Bachelor Parties which probably came at the last time that would be a graet thing - they were both excellent, gave us tons of stories and will live in infamy. The fact that I have five years ahead of this says more about how lucky I've been than any reflection on 2024.
2018: Mexico City, Montreal, Vancouver, Salt Lake City, Egypt & Cape Town, Mumbai, Paris, The Holy Land
This is quality over quantity point, but it hides some truly meaningful, important and wonderful trips. First, that Egypt & Cape Town one - probably still to date my favorite trip I took alone. Egypt gets a lot of hate, but I loved it and still think the feeling of floating down the Nile is one of the coolest feelings. That was also probably one of my more meaningful, important Cape Town trips. The Holy Land trip was also super meaningful, as much for the religious pilgrimage of Jerusalem (which yeah, even as a sometimes Catholic, was damn powerful...) as the incredible back to back days of Wadi Rum and Petra. Those two trips are really high up in my view, which elevates the rest of the year, which is also quite strong. Mexico City was my first Birthday Trip to Latin America with my friends, and my first real time seekign out Michelin Star cuisine (at Pujol) which has become something of an obsession (for better or worse). Montreal was a brilliant Bachelor Party that has led to so many running jokes in my firend group. Salt Lake City was one of my more important trips of my life, starting a so far continuing love affair with not only that city but that part of the country. Finally, Mumbai was my first time doing a crazy far away trip for a stupidly short amount of days (left on a Wednesday Night, arrived back Monday morning), which is something I've repeated now a few times, including once more to Mumbai, and this was probably my favorite Mumbai trip. Every one of these was just awesome - including the Paris weekend which was to watch my Sister get engaged. Just a wonderful year, even if I didn't travel for work too much which limited the local trips.
2026: Mexico City, Denver, Phoenix, Vietnam & Thailand, San Diego, Salt Lake City, Spain, Minneapolis, Japan, OKC, Cape Town
It's hard to judge the most recent year, which probably has come close to maximizing my pace, primarily with loading up on weekend trips - the Denver, Phoenix, San Diego, Salt Lake City, Minneapolis and OKC of it all. All of these were fun, and I will always stan for the Western half of our country, however hard to say that any of these were better than earlier trips to those same locales (only OKC was a new location). That might be the reason I don't have this higher up to be honest - so many of these were repeats. Now, most were repeats in a great way where I did some new thigns - from Xochimilco in CDMX, to watching Lucha Libre in CDMX to eating at The Wolf's Tailor, to eating at Demi, to discovering the greatness of Convoy in San Diego, but a lot of it was replaying the hits - determined not to do as much of that in 2027. The new places are those ain trips from seeing Chiang Mai and Danang, to seeing Kyushu and giving my parents the joy of visiting Japan. That last bit will be hard to top - my second real trip to Japan met every expectation, if not exceeded some. A quick word for Spain, which was me workign during the week but seeing Toledo, Zaragoza and Bilbao during it - great trip but also one that can open a world of such "work in Europe for a week" trips to come, which is important. In the end, the new stuff was incredible, but a lot of reptition - fun in the moment, but doesn't elevate it above the years to come.
Tier IV - The End of Covid
2022: Cape Town, Lima, Zion, Minneapolis, South Korea Trip + Bangkok/HCMC, Phoenix
Objectively, I did more traveling in the years I just covered than this one. That is true. I didn't travel too much for work this year, so my domestic trips especially were minimal. That said, this year will be relatively goated because it was the year the world went mostly back to normal, and that was such a thrill. The best example of taht is the Cape Town trip - Cape Town in the country where the Omicron variant started, the variant that to some degree ended the pandemic. I went on that trip and ironically caught Covid there, but the trip itself was wonderful - including my first long haul fligth in proper Polaris with a window seat landing in front of Table Mountain. The rest of the yaer was great - from luxiury (my only real First Class flight to Seoul, my first time at Anan, my first time to Gaggan when he was there a lot) to fun (hiking the Narrows, discovering the brilliance of a Birthday in South America) to just inexplicably brillaitn (the sculpture garden in Minneapolis). The South America one is important - the success of this short trip to Lima begat a lot of other trips and me really tripling down on that Continent, a truly seminal trip. There's a reason why my pace of traveling incraesed right after this - part of that is more work travel, but mostly because each one of these trips both short or long were brilliant and really reinvigorated my love for travel in a world where that was now much more possible than before.
Tier V - My Peak
2023: Palm Springs, Victoria Falls & Cape Town, Buenos Aires, Scotland, Lima, Japan + Bangkok / HCMC, Phoenix
Now we are really talking. This year had everything. Multiple trips with my main friend group (Palm Springs and Scotland), just legendary trips with my family (Vic Falls & Cape Town), trips with my work friends (Buenos Aires) and trips with just me (Japan + SE Asia). All of these iterations were lovely, and then throw in a weekend to Lima to experience Maido and Central at their best for fun. Hard to know where to start - I don't think there was a single year where every trip graded out so highly. The Vic Falls adn Cape Town one is the standout - just the extra points for watching my parents fall in love with Cape Town the way I did so long ago. That was worth so much of this by itself. Seeing Japan in reality for the first time was so high up as well, a country I have grown to love, and seeing it in about as good conditions as possible (in retrospect, got SUPER lucky with weather). It may have been my favorite HCMC time as well - the best mix of fun and sights. Let's not underrate the Scotland factor, a lovely short trip with friends in the middle of that all. In the end, those two main tentpole trips really drive this year up in my grading, including the fact that every other one was just perfect in its own way, albeit shorter. Much like 2018, this is quality over quantity, but the true apotheosis of that maxim - every one of these was a 9/10 if not outright 10/10, and the 10/10s grade amongst my favorite trips ever.
2025: Tampa, Brazil + Santiago, Phoenix, Salt Lake City, Minneapolis, India & Australia + Auckland, Oaxaca, Cape Town, South America All Over
It's weird that looking back, I didn't feel this level of love for the travel this year in the moment, until in reality that Cape Town trip which was my favorite time in Cape Town in a while, from it being first time at Fyn, and maybe more importantly first time in non-Feb since 2018. But looking back, all of these were insane. The local trips (Tampa, Pheonix, SLC, Minneapolis) were all excellent, including discovering Walter's Wherehouse (Pheonix) or re-discoering the brilliance of The Loft (MSP), and hiking through snow in Cottonwood Canyon. Oaxaca was its own dream - a great little trip to Mexico to experience foodie and mezcal heaven. But let's be real - the reason this is #1 is the long trips were all just brilliant. I still don't know why I resisted going to Brazil for so long, but every bit of that trip from Rio to Iguazu to tagging on my favorite South American city on the backend, was great. That is probably my favorite single one-week trip ever. India & Australia was not the best two week trip, but the relaxed nature of it was super fun and memorable. Finally, what to say about teh South America trip - the longest of my life (granted, worked the first week). The most complex - so painstakingly planned, but so darn successful as well. The magic of the Atacama is worth a 10/10, but add to it things like Colca Canyon, or hiking up Cotopaxi (to an extent), to the seals in Lima, to so much more. I don't know if I will have a year like this again. No year combined this level of quantity of trips and quality of all of them. Some definitely came close, but if I have to be honest with myself, this is nearly as good as it can get. Already 2026 was slightly lesser, but let's see if 2027 can top it...
