My Personal “Most Fun Cities” List

Recently timeout.com made a list of the most fun cities in the world. This list included 18 cities, and I’ll admit, I’ve only been to about a quarter of those places.

Still, I don’t really agree with some of their choices, and while I sadly have to limit my list to North America and Europe, I can’t pretend that I’ve yet been able to satisfy my dreams of visiting Great Britain, Norway and Sweden, Turkey, Israel, Egypt, Morocco, Japan, Australia, and Thailand…at the VERY least. That said? I know I’ve been lucky to travel as much as I have. Privileged, even. So this Thanksgiving, I’m thankful for the chances I’ve had to explore this world and I hope that I’ll have more of them 🙂

But I still have my own opinions about the most fun cities out there, and I also don’t think 18 is a high enough number…even if I were to include every city in the Time Out article. Again, this is coming from someone who has been to many Caribbean islands, almost 3/4 of the states in the U.S., and a dozen European countries. I’m sure there are likely Asian, Scandinavian, Middle Eastern, African, and/or Australian locations that should be added…but I stand by my personal North American/European selections for now.

While I do believe that some of these cities are more fun than others, I couldn’t possibly put them in any order that I’d be 100% satisfied with, so instead I’m just going to list them alphabetically 🙂

Amsterdam, The Netherlands
My sister and I spent several days in Amsterdam in 2007. It was a long time ago, but on my first day there I knew that this was one of those cities I would be obsessed with returning to at some point in my life. We experienced art, we experienced history, we experienced food, and we experienced partying…partying in ways that can’t be described, ways that you can only experience in Amsterdam.

Most Fun Cities Amsterdam

Berlin, Germany
Berlin was one of those places that I considered a stop on the way to somewhere better, and to be honest, even after spending several days there I was ready to move on. (It didn’t help that a lot of our time was spent doing things like walking up and down the Berlin Wall, visiting a nearby concentration camp, and other such unhappy historical things.) Anyway, what’s important is that after I moved on, I couldn’t get Berlin out of my head. I still can’t. It is, like Amsterdam, one of those places I’m dying to visit again.

Most Fun Cities Berlin

Boston, Massachusetts, USA
I’m from New England, so I had to include a New England city, of course! While I’ve had amazing times in Providence, Rhode Island and in many little New England towns scattered throughout Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, and Maine…Boston is always the place that stands out. The breweries, Boston Common, the Freedom Trail, Cambridge but also its *nightlife*, and of course Fenway (especially if you can see a Red Sox game). And honestly, combine the breweries and a Red Sox game and some of that nightlife and you can’t help but have a great time.

Most Fun Cities Boston

Budapest, Hungary
There’s a lot to love about Budapest. The crazy public transportation, the confusing money, the castle on its hilltop (and the cellar wine tastings that can be found up there), the thermal baths, the beauty combined with a lively vibe that you almost wouldn’t expect…add all of that together and I can’t imagine not having a good time in this gorgeous city.

Most Fun Cities Budapest

Charleston, South Carolina, USA
There’s literally nothing better than a random weekend in historic downtown Charleston. I’m not big on shopping, but doing it here is a total blast, mostly due to the open market – but there are also some great art galleries/stores spread throughout the historic district. There are carriage tours, walking tours, even tours by car that will tell you everything you want to and more about the city…and at the end of the day, there’s “The Original” Pub & Brewery Tours of Charleston, which offers the best historical pub tours and brewery bus tours in the city, as well as other events throughout the year. I’ve been on three of their tours and I can’t speak highly enough of them! (P.S. Charleston has great beer and don’t let anyone tell you otherwise!)

Most Fun Cities Charleston

Chicago, Illinois, USA
After several trips to Chicago the best thing I can say is that I still don’t feel like I’ve experienced enough. The museums, the lakefront, and the Miracle Mile are all great; but that’s nothing compared to a Wrigleyville party, a pizza pot pie and some wine or beer paid for in cash at Chicago Pizza & Oven Grinder, a night at Second City, or a baseball game. Chicago is easy to navigate and there is something for everyone and I know I’ll return again and again.

Most Fun Cities Chicago

Denver, Colorado, USA
Denver is another place that surprised me when it came to mind as I made this list. But then I realized that it’s close to a major airport, close to amazing skiing, and has its own fun draws as well. If you’re up for a toke, for instance, pot is legal…but the last time I was there the most fun thing was to map out a brewery tour that left from my hotel and circled back around to it. The best thing? This tour allowed me to walk no more than a half mile at a time (and even that longer distance only happened twice between stops), visit (in the end) half a dozen Denver breweries, and just generally lead me on a fun tour of the city. There is so much to do in and around Denver that I can’t imagine anyone not loving this place.

Most Fun Cities Denver

Dublin, Ireland
I’ll admit, I visited Dublin just once…and it was over 16 years ago. But the fact that it hasn’t faded from my memory even after all this time is what says a lot. I was awkward and shy in high school, and I’d only just started coming out of my shell when I ended up in a college that shoved me right back into that shell…only thankfully, around that time I had the opportunity to go to Ireland for spring break as part of a study program (including a scholarship that paid for most of the trip), and I fell in love with Dublin the moment I stepped off the bus from the airport. It was March, it was dreary, and it was beautiful. The Guinness brewery was a ton of fun, the Temple Bar area was great, and everywhere I went, people wanted to talk to me. I don’t mean for that to sound stuck up; I was used to being in the background, feeling awkward at the least and anxious at the worst. But suddenly, in Dublin, I felt *alive*. I felt like I was part of things. And that memory has never left me.

Most Fun Cities Dublin

Greenville, South Carolina & Asheville, North Carolina, USA
I think I would be remiss if I didn’t include Greenville, because despite growing up in Connecticut and living in Massachusetts, Virginia, and the Orlando area off and on, Greenville is the one place I always go back to. Sadly, while I can’t admit that it deserves an entry all its own, by combining it with Asheville (which also doesn’t deserve an entry all its own), everybody wins. Greenville has some great restaurants, bars, and breweries – and if you’re a Red Sox fan, seeing their farm team (The Greenville Drive) at Fluor Field is a must. Combine that with even more breweries in Asheville, the Biltmore House (which has a winery and a tour that includes samples), and the generally picturesque surroundings, and you can have an amazing long weekend and still not experience everything that this area has to offer.

Most Fun Citites Asheville

Most Fun Cities Greenville

Key West, Florida, USA
You know what the most surprising thing about Key West is? Technically, you’re *not* supposed to have open containers on the streets! But you know, just don’t be stupid and you won’t have to worry about that 😉 That said, there are tons of other awesome things to experience here…the Southernmost Point, the Hemingway House, Blue Heaven for brunch (great Bloody Marys!), Cuban Coffee Queen if you need a pick-me-up, Sloppy Joe’s or the Green Parrot for late-night bars, and Fort Jackson if you want a good beach. Most of the historic district is walkable, there’s plenty of other stuff to do, but let’s not lie – Key West is mostly about the party.

Most Fun Cities Key West

Las Vegas, Nevada, USA
Does. This. Even. Need. An. Explanation?
I could say gambling, clubs, great restaurants, no open container laws, champagne brunches, shows, and more, but…
The answer is no. You really only need pictures. (And I’m only going to include one picture each from my last three Vegas trips – just FYI, I’ve been twelve times!)

Most Fun Cities Las Vegas

Most Fun Cities Las Vegas

Most Fun Cities Las Vegas

New Orleans, Louisiana, USA
I’ve been lucky to have not one but two amazing trips to NOLA. The first time was during Mardi Gras season – not over the holiday itself, but as it happened we were there when the Saints won their first ever (and so far only) Superbowl…and the second time was for Halloween, which was a complete blast, if not quite as epic as my trip there in February 2010. Regardless, there’s so much more than Bourbon Street (although that’s quite a party) and the French Quarter…there’s Frenchmen Street if you want some great music, the Garden District if you want to see gorgeous houses and other historic sites, Tipitina’s for even more great music…and one more quick French Quarter shout out, Napoleon’s for the food and the Pimm’s Cups. The people are friendly, there’s history and nightlife…what more could you want?

Most Fun Cities New Orleans

Orlando, Florida, USA
Walt Disney World. Universal Studios Orlando. Church Street. Lake Eola Park. Some of these things surely sound familiar to you while some of them may not, but all of them are amazing. Is Orlando historical? No. Is it beautiful? Not really. But if you want to have some fun, you can drink around the world in EPCOT at Disney, try brews in Diagon Alley and Hogsmeade at Universal, hang out in the Church Street Station area, or even just take a walk around Lake Eola Park and check out some of the bars and restaurants in that vicinity. But hey, let’s not lie, you’re more likely to come here for the theme parks qwe454or a convention 😉

Most Fun Cities Orlando

Most Fun Cities Orlando

San Francisco, California, USA
I think the best part about San Fran is that you can visit all of the touristy places and also fit in a few less likely stops in just a few days…and in those few days, there are plenty of fun options that don’t involve the touristy stuff. But really, how can you convince yourself not to visit Haight-Ashbury? Or if you’re a geek, find George Lucas’s house with the faux robot out front? And don’t even get me started on hanging out in Alamo Square to get a picture of the Full House house in the background. If you’re a baseball fan and can afford the drinks, the Giants stadium is gorgeous (with a great view) and they keep the alcohol flowing. Then there’s the usual stuff like Fisherman’s Wharf, Alcatraz, and of course the Golden Gate Bridge. I honestly can’t even imagine visiting this city during Pride; it would probably be the most amazing experience of my life. Everything about San Fran is fun and welcoming and there always seems to be some sort of party going on.

Most Fun Cities San Francisco

Vienna, Austria
There’s these sausages you can buy. They hollow out a small loaf of French bread, pour some sort of life-changing mustard sauce in it, and then insert a cheese-infused sausage. And it’s the best thing I’ve ever tasted. It’s the perfect late-night snack, or hey, you can have it for lunch (with a cold beer) in the middle of the day…all while exploring the gorgeous sites of Vienna. The Spanish Riding School, St. Stephen’s Cathedral, and the Schonnbrunn Palace, just to name a few. There’s also the infamous Vienna Schnapps Museum, and, if you’re looking for nightlife, the area they call “The Bermuda Triangle“. I sincerely believe that there’s something for everyone in Vienna, and when I explain it to people I call it “the other Paris” – where people are more friendly, accommodations are cheaper, and you can actually experience the local festivals without fighting to be there in every way possible.

Most Fun Cities Vienna

Maybe this is too little too late, and above all please excuse me for using so many pictures of myself. One never knows how one’s friends will take to being featured in a blog entry, after all 😉

I’d love to hear some input on the best Middle Eastern, African, Asian, and Australian cities, so please feel free to leave a comment. There are a lot of places on my “to visit” list, but it can’t hurt to make that list longer and hope for opportunities! For instance, I didn’t list any cities in Alaska or Hawaii, which are both must-sees in my opinion, but sadly don’t include a “most fun city” (at least in my opinion). Like I said, though, I’d love to hear your thoughts!

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