Here are the places I’ve been, ranked not necessarily in order of how much I overall enjoyed the cities in general – but in terms of how Holiday-ey they felt as a “Holiday Season Destination.”
17. Shanghai
Technically this was a work trip I took to Shanghai in December 2010, so I wasn’t really going there for “Holiday Season” purposes. But to be fair, I travel for work – so a handful of these trips were actually work trips. What do I remember Christmas-ey or Holiday-ey about Shangahi, China? Nothing. I don’t remember a single Christmas tree decoration. I do remember “Colonel’s Fried Chicken” and other copywrite-violative stores on the streets. This trip could have been in July and there would have been no difference.
16. Abu Dhabi
Another work trip. I mean there is no real reason for a Muslim country to get too much into the Christmas spirit – but I do recall my hotel’s lobby at least having a Christmas tree up in it in December 2022. Which is more than can be said for Shanghai.
15. Buenos Aires
I was around Buenos Aires in December 2018 and I do recall a few Christmas decorations on the streets, especially around that big obelisk thing that sort of looks like the Washington Monument. Still, beyond that I don’t really recall any major “Christmas vibes” from this trip.
14. Philadelphia
To be clear, “visiting family” doesn’t count as a “Holiday Season Destination.” I’ve visited extended family / in-laws in Philly a lot of years around Thanksgiving, but this isn’t what I’m talking about. I’m talking about the one time I went to Philadelphia around November/December back in 2009. I know this place is famous for having the oldest Thanksgiving Parade in the US (older than Macy’s in New York) – but other than that… meh. Can’t say anything makes Philly a top Holiday Destination.
13. Valetta, Malta
No offense to Valetta or the nation of Malta – I loved it here and this was a great trip I took in December 2017. And I do recall some pretty Christmas decorations lining the streets of Valetta. But again, when I think back on this trip I don’t think much about it being a “Holiday Season” trip. I do, however, think A LOT about drinking until I was shitfaced at “The Pub” (the same Pub where Oliver Reed died filming “Gladiator”) and going on a Game of Thrones filming tour around the island the next day while absolutely hungover.
12. Seattle
Around Christmas/New Years 2015 (turning into 2016) I’ve visited Seattle. It was a good trip. Did the Space Needle on New Years Eve and saw the last sunset of the year from atop it. Then I missed the fireworks because of a fairly late dinner reservation, followed by being unable to navigate to the waterfront in time to get a view of them. Like Malta, a fun trip where I did a lot of fun things – but none of it felt too “Holiday Season” focused, and I feel like this trip would have been about he same any time of year I visited it.
11. Bangkok
This was intentionally an anti-Christmas trip I took on Christmas. I went to a warm, topical destination and hung out at a luxury hotel eating the most amazing mangoes I’ve ever had in my life for breakfast every morning. I went to temples and took daytrips to ruins. I literally cannot remember anything Christmas-ey at all about this trip, but since I was purposefully taking it as an anti-Christmas trip on Christmas, I suppose it’s ironically a great Christmas trip? I dunno.
10. Hong Kong (and Macau)
This was in December 2010 – the same month and year I went to Shanghai. Yet it was interestingly enough a completely different trip. Flew out to China for work, flew back home, then like two weeks later flew again to Hong Kong, which at the time was still China Lite with little bits of democracy and freedom in it. Hong Kong ain’t like this anymore, that’s for sure. Unlike Shanghai though, I do remember some Christmas decorations, as the legacy of it being a UK territory was still lingering at the time. Like Bangkok, sort of an anti-Christmas trip to get away from traditional Christmas stuff, but surprisingly a little more Christmas-ey than I had imagined because I do remember jazzed-up Christmas lights on the sides of buildings, and hotel lobbies with pretty displays.
9. Honolulu
If I recall right, this was a little closer to Thanksgiving than Christmas in 2011, but still Holiday time. There is something cool about the tropical version of Holiday season decorations with Santa riding a surfboard rather than flying around in the snow. Still, eating at a Japanese BBQ for Thanksgiving instead of having Turkey? Highly recommend.
8. Brussels
I’ve been to Brussels a million times for work, and I think twice (2008, 2011) were around Christmas. It actually might have been more and I’ve lost count, but let’s go with those. Yes, they put up a good holiday display and a tree in the Grande Place, but the real reason Brussels is a nice little Christmas city is all the Christmas beer that Belgium has. Belgium is an ale country, and all the nice spiced ales are wonderful. Basically, that’s all I need to confirm this as a fairly cool Holiday destination.
7. Chicago
I’ve actually been to Chicago around Christmastime twice – in 2009 and in 2021. I really enjoy the Second City and it’s certainly a city that puts up large Christmas displays. It also feels like a good place to visit during cold weather times. But man was it cold here the first time I went. Like VERY, VERY cold. Super cold. Cold I would never feel again in my life until… well… I guess we can talk about that a little more later. Still, I think I’d rather go to Chicago during St. Patrick’s day and re-create scenes from The Fugutive. Not that I didn’t do that when I was there for Christmas. Because I did. Nothing like going to the Hilton, finding the ballroom, and re-creating that “All so that RDU-90 could be approved and Devlin McGregor could give you... Provasic!” scene.
6. New Orleans
I went to the Big Easy in Christmas 2014 and then again for Thanksgiving 2015. If I remember right, it was all based on an initial Google search of “top cities to go to for Christmas.” It was a good choice because New Orleans is typically a humid armpit, but at least over the winter it’s mild and pleasant. And as a fairly Catholic city, NOLA fit the bill pretty well. There were Christmas-decorated old houses that you could visit, the famous cocktail bars were all dressed up. My one complaint might be that it’s so Catholic a city that on Christmas Day itself basically everything is closed. Which I suppose might be common in a lot of cities but still… sort of sucks that you’re there on Christmas Day and can basically do… nothing. All the other days around it though? Solid.
5. London
Last year I took a Christmas-to-New Years trip to London. This is one of my favorite cities, and of course London is famous for shopping and it many of those famous shopping streets were decorated for the Holidays (I actually did a Christmas lights tour too atop a double decker bus). But I suppose the highlight of this “Holiday” season trip was more New Years than Christmas, as I stayed to watch the fireworks shooting out from the Lonon Deye over the Thames which were AMAZING. Great trip, lots of Christmas markets in many of the famous squares and parks, and it definitely felt like the Holiday season when I was there.
4. Berlin
I said that I considered the “Holiday Season” to begin Thankgiving-ish (stress on the -ISH) because this trip I actually took in early-to-mid November 2011. Despite that, the Christmas markets were already open. Is Germany a fantastic place to visit during the holiday season with Christmas markets? Yes, it absolutely is. I do have very vivid memories of the Christmas Market at Potsdamer Platz (technically “Winter World,” I believe) that had a big snow slide, snacks, mulled wine, and handmade crafts. Again a work trip, but I was pleasantly surprised about how much it already felt like the Holiday season… a little early.
3. New York City
I’ve been here once on a work trip coincidentally during mid-December, and then another time on a holiday trip specially to be there at Christmastime. And what’s not to love? The Macys windows and all the window displays along 5th Avenue. The skating rink by Rockefeller Plaza. NYC is TOTALLY a great Christmas destination. If you can afford the hotels in Manhattan that are fairly damn pricy at normal times, let alone Christmas.
2. Quebec City
When I was talking about Chicago, I mentioned the cold. But Chicago cold has nothing on Quebec City cold. Like New Orleans, it came up on a list of “great cities to visit for Christmas.” Like New Orleans, the list was correct and this WAS a great city to visit for Christmas. Like New Orleans, it is a very Catholic city and therefore basically everything on Christmas Day itself was closed so there was little to do on that day. But unlike the Big Easy, Quebec City was cold cold cold cold. Unbelievable cold. I’ve once been to Mongolia in February and while Quebec City wasn’t THAT cold, it was close. Still, if you want to feel like you’re actually visiting Santa at the North Pole… well… Quebec has that vibe. And the Christmas decorations… the Christmas markets… the special Christmas activities and toboggan races (outside the gorgeous Fairmont Le Château Frontenac hotel) , etc… all amazing. But whatever winter wardrobe you think might be appropriate to wear… it’s not enough. This is literally “your phone will stop working” cold. This truly was a Winter Wonderland.
1. Munich / Saltzburg / Vienna
Is it sort of cheating or unfair to lump all three of these amazing Austro-Germanic cities together as one ranking? Maybe. It is also lazy! However, in 2016 I went on a three-city trip to these three places at the end of November and beginning of December and it was incredible. Everything I said about Christmas markets under the Berlin entry apply here times ten. All the cities were amazing and incredible to visit during Christmas, and I highly recommend. I was also there for the Krampus run night (remember in the alternatives to Santa Claus ranking where I talked about them beating you with sticks? Yep… this is from that trip). Christmas markets. Decorations. Food. Drinks. Snow. There was even a quick day trip to Hallstatt on this trip, which sort of looks like a fake Christmas card painting in December… but it was REAL and I saw it with my own eyes.
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