What are amazing cities to visit for ONLY 1 or 2 days?
November 2, 2016 6:14 PM   Subscribe

So I've got this round the world ticket. And I've got a little over 3 weeks to use it. So I want to see as much as I can in the time. But I don't want to blow through places that clearly deserve more time to see. I did that in Vienna and regretted it. So what are the best cities in the world to see for just limited times. As in, VERY worth seeing but spending MORE than two days seems excessive.
posted by rileyray3000 to Travel & Transportation (53 answers total) 36 users marked this as a favorite
Sintra, Portugal.
posted by googly at 6:20 PM on November 2, 2016

Heidelberg, Germany.
posted by praemunire at 6:26 PM on November 2, 2016 [2 favorites]

Antwerp, Belgium
posted by knile at 6:27 PM on November 2, 2016 [2 favorites]

Reykjavik... though I guess you'd want to spend more time in Iceland as a whole. Also, Bruges, Belgium.
posted by gemutlichkeit at 6:27 PM on November 2, 2016 [4 favorites]

I know it's very touristy but Vegas is a two day trip. Gives you the right amount of time to see the sights and get the feel of the city.
posted by GilvearSt at 6:29 PM on November 2, 2016 [4 favorites]

Where do your parents and other relatives live? Maybe that kind of thing would be a good use for this.

Also, you could go to a special concert or art exhibit you're interested in, or to view a particular event.
posted by amtho at 6:32 PM on November 2, 2016 [2 favorites]

Seconding Antwerp. Well worth a visit!
posted by Threeve at 6:37 PM on November 2, 2016

Weirdly enough, Lyon, France. Maybe it was because I was living in France at the time but a dinner at Bouchon des Filles, a walk around town and some cheese for the plane and you're set. (Bonus points if you can make it for Fête des lumières)
posted by raccoon409 at 6:39 PM on November 2, 2016 [1 favorite]

Bologna, Italy
Venice, Italy (I know many will disagree with me here and say that Venice requires more time)
Bergen, Norway
And seconding Sintra, Portugal
posted by tango! at 6:40 PM on November 2, 2016

I think you could reasonably do Sofia, Bulgaria, in two days, should you find yourself in that part of Europe.
posted by mykescipark at 6:55 PM on November 2, 2016

Arles in France.
posted by mskyle at 6:57 PM on November 2, 2016 [2 favorites]

Toulouse, France
Valencia, Spain
Strasbourg, France
Cordoba, Spain
Delphi, Greece

You probably could do Athens in 2 days too.
posted by clarinet at 6:58 PM on November 2, 2016

Pisa is a one-day trip. See the tower, take a funny picture, go somewhere else.
posted by Elly Vortex at 7:01 PM on November 2, 2016

Porto, Portugal. Haarlem, the Netherlands. Bonus: near the airport!
posted by Valancy Rachel at 7:09 PM on November 2, 2016

In researching a Greek vacation, the general consensus was spend 1 day in Athens and then get out.
posted by tatiana wishbone at 7:18 PM on November 2, 2016 [1 favorite]

Dubrovnik--beautiful city, but very compact.
posted by carrienation at 7:18 PM on November 2, 2016 [1 favorite]

Tbilisi, dear god Tbilisi.
posted by Cosine at 7:20 PM on November 2, 2016 [2 favorites]

You could do Hong Kong in 2 days. It would be short but not criminally so.
posted by ch1x0r at 7:25 PM on November 2, 2016 [2 favorites]

Venice Italy yeah
posted by greta simone at 7:31 PM on November 2, 2016

Also Nice
posted by greta simone at 7:31 PM on November 2, 2016 [2 favorites]

Oh, and Genova, Italy
posted by clarinet at 7:33 PM on November 2, 2016

Salzburg, Austria
posted by Neekee at 7:36 PM on November 2, 2016 [5 favorites]

Dubai. 1.5 days is perfect.
posted by trialex at 7:50 PM on November 2, 2016

Fairbanks, Alaska: visit Circle Hot Springs, see the northern lights (epic this year I've heard), and visit a sled dog racing kennel. Done.
posted by fshgrl at 7:58 PM on November 2, 2016 [2 favorites]

I'm with amtho on this. Rather than trying to "do" two day cities, pick the cities you want to go to, and give yourself a two day goal in each. I used to do "find the cool used bookstore the cool kids visit" when I traveled or visited. (In a round about way, that's how I met my wife.) So, don't worry about doing what should be done in any given place. You do what you want done (bookstore; find local hero artists; get the best local baked good; see how they do your favorite food; whatever), and in the process you will get down into some nooks and crannies and you won't feel bad about missing anything.

Whatever you decide, you're going to have a great trip, and I'm really envious.
posted by notyou at 8:00 PM on November 2, 2016 [5 favorites]

Krakow, Poland. Visit the market, hear the trumpet, and take a day trip to Oswicem/Auschwitz. You could do this in one day.

Also, plan to spend a day or two in Prague.
posted by bendy at 8:07 PM on November 2, 2016

Anthony Bourdain's Layover kinda fits this city in a day theme. His Singapore and a Taipei episodes were fun!
posted by inevitability at 8:30 PM on November 2, 2016

Dubai. Abu Dhabi. Halifax.
posted by jessamyn at 8:35 PM on November 2, 2016 [1 favorite]

You might be interested in watching the TV series "Travel Man" with Richard Ayoade. The entire concept of the show is 48 hour visits to different cities.
posted by kickingtheground at 8:43 PM on November 2, 2016 [2 favorites]

Dubrovnik, Croatia
posted by Mr.Know-it-some at 8:46 PM on November 2, 2016

We did Lyon in 2 days, but could have used a couple more just to eat more of the delicious foods available.
posted by matildaben at 8:55 PM on November 2, 2016

I wonder if you wouldn't have a better time if you spend less time in transit? That said, there are so many dreamy possibilities with something like this. What I'd do is try for an itinerary of several close-together cities in one part of the world, then several more in another. I'd also be conscientious about picking places with similar weather, so you're not stuck bringing snow boots and a bikini on the same trip. Anyway, here's my own dream-trip, with much too much for such a short amount of time:

New York [I'm assuming that's your starting location]

Lisbon, Portugal
Rabat, Morocco
Athens, Greece

Colombo, Sri Lanka
Yangon, Burma
Bangkok (or another major hub in SE Asia)
Hong Kong, Hong Kong
Taipei or Kaohsiung, Taiwan
Hiroshima or Osaka, Japan

New York

I don't know about Havana, Rabat, or Sri Lanka, but everything else except for Yangon shouldn't require a visa if you're a US passport holder. Yangon now has a type of e-visa for visitors arriving by air, though it costs $50 and requires you to apply online a few days in advance if I remember correctly. India has visa-on-arrival for thirteen of its largest airports (be sure to double check!) if you'd rather that than Sri Lanka. I believe Vietnam is the only country in SE Asia (besides aforementioned Burma) that isn't visa-on-arrival.
posted by tapir-whorf at 8:59 PM on November 2, 2016 [2 favorites]

You can hit the highlights of Edinburgh in 1-2 days.
posted by Eyebrows McGee at 9:37 PM on November 2, 2016 [1 favorite]

Nobody mentioned Barcelona. It has maybe the best restaurants in Europe. If I had the money I'd fly there tomorrow just to get lunch at Quimet-i-Quimet and dinner at Tickets.
posted by dis_integration at 9:41 PM on November 2, 2016

If you're going to Sri Lanka, spend the time in Kandy, not Colombo would be my suggestion.
posted by peppermind at 11:21 PM on November 2, 2016

Athens, Greece - visit the ruins and beachside coffee houses by day, walk around the plaka at night, eat the most delicious grilled meats and salads at Thanasis.
Kuala Lumpur, Malaysia - temple tours, street food, jungle walks, markets.
Singapore - the zoo, Jurong bird park, chilli crab, afternoon tea at Raffles, shopping and dining in Little India (love the Mustafa Centre).
Venice, Itay - ride the vaporetti and walk around for 2 days eating gelato.
Trieste, Italy - beautiful architectural and park walks.
Stresa and Lake Maggiore region in Italy - mountain-biking or walking, sunset cocktails at the Lido Palace hotel, walks along the lake, mansion gawking.
The Champagne region in France (you could do one night in Reims, and the other in Epernay) - drink all the Champagne cellar doors and bars, and eat all the cheese from La Cloche a Fromage.
Adelaide, Australia - one day in a wine region (you can do the Adelaide Hills and the McLaren Vale in one day), then relax on a southern beach.

(YMMV: I thought two days was plenty in Vienna!)
posted by travellingincognito at 12:31 AM on November 3, 2016

Cardiff, Wales. One day for the castle and arcades, one day for the bay (and Dr. Who experience, if that interests you).
posted by penguinicity at 2:31 AM on November 3, 2016 [1 favorite]

Bergamo, Italy, and for se Asia I would not do Bangkok- it's too big to get a handle on in 2 days and you'all probably just end up stuck in traffic. Luang Prabang, Laos, would be my se Asian pick.
posted by jojobobo at 2:42 AM on November 3, 2016

Seconding Cordoba, Nice, Valencia, Pisa, Bruges, Porto, Bologna and Edinburgh.

For me personally, Barcelona is like Vienna -- you could certainly spend a wonderful two days there, but you'd leave feeling like you hadn't seen half the stuff you wanted to. Venice is kind of on the edge. You could see the specific big-name tourist sites in a day or two but I think it's worth having three or four days there just to leisure wander around.

I would also add:

Bath, England
Cambridge, England
Carcassonne, France
Arles, France

Also, if I were planning this kind of trip, I'd spend some time looking at the list of UNESCO World Heritage Sites.
posted by yankeefog at 3:18 AM on November 3, 2016

Budva montenegro
posted by chasles at 4:19 AM on November 3, 2016

Beware of jet lag, stick to one main region and try to pick places near airports otherwise you will burn time in planes, buses or trains.
posted by epo at 4:48 AM on November 3, 2016 [1 favorite]

Travel time is a big consideration if you've only got 3 weeks to get round the world. Darjeeling would be amazing but you'd spend another day getting there from the airport and back. Your round-the-world ticket also presumably has practical limits on which airports are easily accessible.

I'd second Porto, Bruges, Athens, Tbilisi, Dubai and Luang Prabang. All worth seeing.
Also Malta: it's compact and you can see Valletta and Mdina in 2 days.
Not convinced by Cardiff or Genova (though the Cinqueterre is a possibility)

Although it would dictate a decent chunk of your itinerary, you're probably not going to make it out to Easter Island without a round-the-world-ticket.
posted by doiheartwentyone at 4:53 AM on November 3, 2016

Check out the New York Times' 36 hours series in such and such a location. That said, realize you're going to spend at least two traveling days to and from each city. This is likely to be exhausting process which may turn the mini-trips into blurs. It takes a certain amount of time on day one just to get oriented. Make sure you book lodgings in the prime location of the city you're visiting, so you can do most of your sightseeing on foot. Scope out restaurants and sites before you get there. Bon voyage(s).
posted by Elsie at 6:41 AM on November 3, 2016

Singapore -- it's got AMAZING food, good shopping, and some interesting architecture and gardens, but I think you can do it in two days and leave and feel satisfied. As a bonus it should be very easy to fit it on any RTW trip as it's a huge airline hub.
posted by andrewesque at 6:55 AM on November 3, 2016

I second Elsie's recommendation to check out the New York Times' 36 Hours In... column. It is designed for just this kind of trip and often focused on emerging/second-tier-but-still great places, and centered on one part of town or a new cool neighbourhood for bigger/first-tier cities. Many of my links are from this column because I've found it so useful. Some autoplay video - beware.

My list of cities that this would work in is mostly European and Asian; I do little vacations all around Asia a lot being based in Hong Kong and I used to live in Poland. Remember that you'll get back to lots of these places later in life, so don't panic if you don't see it all!

Overall advice:

- Pick a theme in megacities: record shops? mosques? coffee? plants and flowers? Give yourself a focus and keep coming back to that, like a little meditation, when it's all a bit overwhelming.

- Pick a neighbourhood in megacities and take time to savour street life; if you can stay a bit, but not totally, off the beaten path/out of the main hub of town and find out what locals are up to (Asakusa or Meguro, not Shinjuku, in Tokyo, Sai Ying Pun or Prince Edward, not Central, in Hong Kong, Thonglor or Ari, not Siam, in Bangkok).

- Add all your airline apps to your phone so you can check in easily/without a printer.

- Add the MyFlights app and get flight changes pushed to your phone before the airlines tell you. Here is a review from a miles/points blogger.

- Invest in a better or more expensive guide or tour, especially since your travel is paid for and your accommodation costs are minimal given the short length of your stay.

- Invest in faster transport around town - don't wait 45 minutes for a bus if you can afford an Uber or a taxi.

- Don't overlook first flight in/last flight out day-trips, especially in urban East Asia and northern Europe; for some city pairs with very low-hassle airports like Hong Kong and Taipei or Zurich to London City, this would work quite well. For example:

1) You could leave Taipei at 0600 on Cathay Pacific flight 643, spend the whole day here in Hong Kong, and then fly back on Cathay flight 408 at 2245, getting back to Taipei about a bit after midnight.

2) Swiss will fly you from Zurich to London City at 0640, landing you at 0730. They'll check you in both ways that morning! Spend the day in London and fly back at 2005 (you only have to check in 20 minutes before for European destinations because there are no gates and all the planes are small!), landing back at Zurich at 2245.

- Pack very light; avoid checking a bag; you may land and then start exploring hours before you want to bother finding your hotel.

- Don't forget to eat, and make restaurant bookings to guarantee you get in where you want to go; for places like Tokyo this is important

- Milk this ticket for all the points and miles you can earn to pay for future travel.

- If it's trivial, take the ten minutes to pick up a SIM card at the airport - you'll definitely make up the time/hassle in terms of maps/calling and booking things later (your phone is unlocked, right?). Check out this great wiki: http://prepaid-data-sim-card.wikia.com/wiki/Prepaid_SIM_with_data

OK! The cities...


- Hiroshima/Miyajima is perfect for this. A day for the Peace Museum and okonomiyaki, and a day for the Miyajima hike.

- Kanazawa is like a mini-Kyoto and you can do a daytrip of the main sites, including a fantastic garden, in a long daytrip by bullet train or a flight from Haneda (to Komatsu).

- Takayama/Shirakawa-go (go in the winter and stay in a ryokan!).

- a glimpse of Kyoto is possible in two full days (though you'd fly into/out of Osaka, so budget travel time in).

- Any one part of Tokyo (here's one NYT 36 Hours article of many on the city on the eastern side of the city).


- Seoul is huge but a tightly-planned visit would be rewarding for sure. (And Korea has AMAZING socks! Trust me on this.)

China, Taiwan, Hong Kong, Macau:

- Taipei is fantastically organised for the casual traveler, and has both hot springs and incredible food and markets, but I think it's hard to justify for more than a few days unless you're really into the culture - though the National Palace Museum is probably the world's best collection of Chinese art and makes the whole trip worth it. Don't miss Wistaria Tea House, either.

- Macau is tiny - just 800,000 people - but has a truly unique Portuguese/Chinese heritage and is a window into the twenty-first century given the insane Vegas-like vibe in Cotai to spend two days, and you can fly there from Taipei/most cities in China, but not from Hong Kong (though there are fast one-hour ferries from HK ever ten/fifteen minutes). There's also some comparatively inexpensive five-star hotel experiences available if you travel midweek - you'd pay half for a more luxury-oriented property like a JW Marriott or a Conrad that you'd be paying in HK. If you're a points/miles collector/user this is worth considering.

- Hong Kong is a bit like Tokyo - so dense and ever-changing that a visit of any length is great. Stay somewhere on the Island or Tsuen Wan lines; I tell tourists to stay in Tai Hang, Sai Ying Pun or Yau Ma Tei/Mong Kok. Just walk around - the city rewards exploring on foot - or shop your brains out; there's no sales tax here. If you come to one place in this region, come to Hong Kong.

- Mainland China, sadly, is hard to justify for a weekend unless you already have a visa. US passport holders can get ten-year tourist visas for around $150 USD, but you may not have time to sort out the visa before you leave (it's hard to tell if you're already on the road from your question!). HOWEVER, Beijing, Shanghai, and a number of other cities let you do a 48/72-hour transit visa if and only if you are flying on to a third country (so Japan-Beijing-Hong Kong is fine but Japan-Beijing-Japan is not; Taiwan, Hong Kong and Macau have separate immigration and for all intents and purposes for the tourist are separate countries). That said: Beijing and Shanghai are the best set up for this kind of visit. Xi'an is also probably doable in 36-48 hours but you'd need to enlist a bit of help without Mandarin skills, and be prepared to take taxis more.


Definitely excellent value here, and travelling around by budget airlines like Air Asia or Vietjet is perhaps worth making some changes to your RTW ticket for.

- Luang Prabang - an incredibly well-preserved French colonial old town and the best handicrafts and weaving I've seen in all of the region - check out Ock Pop Tok

- Siem Reap (really, though, three days might be better for Angkor Wat and surroundings!)

- Hanoi - see Ho Chi Minh, have great Vietnamese food, wander around the old town - it's my favourite non-Bangkok city in ASEAN (sadly you definitely don't have time for Bangkok!).

- Hoi An - a gorgeous port town midway down Vietnam's coast, also near Hue, the old imperial capital; fly to Da Nang.

- Yangon - Myanmar's crumbling colonial former capital; has to be seen to be believed! Do a walk with Yangon Heritage Trust - it's the best single excursion I've ever done in an Asian city.

- Penang - Malaysia's island food capital.

- Bali - yes, two days is possible! Especially works well if you're flying from northern bits of Asia to Australia and just want a beach and some sunshine for a bit, and perhaps some jungly time in Ubud. Pick one bit and stay there (Canggu is my favourite laid-back beach area in south Bali; Seminyak much more dense but also doable when I want a bit more access to coffee and better restaurants) and have your accommodation arrange to collect you/drop you off, or get Blue Bird taxis. And get a massage at Jari Menari!


- Delhi is overwhelming but you could hit some of the highlights in two days, for sure. I stayed at the budget-chic Bloomrooms near Jangpura metro station, which saved me a load of hassle. I loved the Mughal architecture of the old city most of all - don't skip Humayun's Tomb, the Qutb Minar, or the Red Fort and Jama Masjid. I also did an Urban Adventures food tour with these folks and it was fantastic (and I didn't get sick!).

- Mumbai is definitely on my list after reading this but I have no first-hand experience.

The Middle East, Caucausus and Mediterranean:

- Istanbul is an obvious choice for a trip like this. Spend one day on each side, Asian and European. Or pass through a few different times. Stay in Cihangir (Europe) or Kadikoy (Asia). Eat all the mezze, and have breakfast at Van Kahvalti Evi (which I would fly to right now if I could).

- I loved Esfahan and its incredible assortment of mosques, squares, parks, gardens and other wonderful monuments. You'd need three days, really, to see the best of it, but in a taxi I think you could hit the highlights in just two. It's much smaller than Tehran and mostly walkable in the centre.

- Athens was fantastic this past spring and deserves a much better reputation. If you can tolerate some grit and dust it's well worth seeing for the classical ruins, and for food from all over Greece. The National Archaeological Museum is also a destination in itself.

- I'm not sure on safety these days, but Alexandria was jewel-like with incredible light at dusk in the old colonial parts of town, and such a rewarding excursion from Cairo (also worth a flying visit! - spend a day at the Pyramids [there's a lot more than just the famous three in Giza - Saqqara was my favourite] and a day wandering in the Old City).

- Tbilisi was stunning and absolutely delicious, but the old centre is very walkable. It is also astoundingly inexpensive compared to the rest of Europe.
posted by mdonley at 7:30 AM on November 3, 2016 [5 favorites]

Response by poster: Some help with the guidelines if you're interested in REALLY getting into it. It's a round the world star alliance ticket. Here's the specifics:

* A business class round the world ticket gets me 39,000 miles.
* Your journey has to start and end in the same country, but not necessarily in the same city.
* Make sure that your journey follows one global direction only (East or West) and crosses both the Atlantic and the Pacific exactly once. You may zig-zag to some extent within each continent.
* Your trip must include a minimum of 3 stopovers and a maximum of 15 stopovers. The number of stopovers and the total mileage flown affects the overall cost of the journey.
* You can include up to 5 surface sectors using the car icon to the right of the city name. The first crossing between continents cannot be a surface sector.

And here's the link if you'd like to play along at home.

As you can see, since I'm only going one direction (no offense to Zayn) then I think the jet lag SHOULD be a little limited.
posted by rileyray3000 at 7:47 AM on November 3, 2016 [1 favorite]

Ah, amazing. Business class is the way to do a trip like this: no queues, comfy seats, loads of luggage space, lounges, and sometimes fast-track immigration. Awesome.

Some specific advice on Star Alliance RTWs:

- Check out Flyertalk's Star Alliance forum. The archives are deep and it's a pretty friendly community. All the specific airlines have their own forums too.

- Flying in business class will earn you, perhaps, quite a bit more than 39,000 miles, since many airline frequent-flyer programs credit more than 100% of the miles flown for premium travel. Checking Where to Credit is important, since it will tell you which airlines will give you the most miles for your buck. Here's what you'd earn with a C class ticket on Scandinavian; note that other airlines' programs may be more generous than that of the airline's you fly, and that the booking class will vary for each flight.

- Use seat maps, review sites and forums to determine which routes will get you the most comfort for your buck. Would you rather have TAP's meh-but-still-nice business-class service from New York to Lisbon and arrive early on day 1, or fly from New York to Frankfurt on Singapore Airlines in their *amazing* business class on the A380, sleep like a log, and then transit via a Lufthansa lounge and flight in their only-ok European business class down to Lisbon, taking longer but perhaps doing it more comfortably? What if you did this trip only using *first* and not just business seats? Or what if you did this trip in economy, with no lounge access?

- Consider a positioning flight to your initial starting point if the RTW ticket price is much cheaper starting from somewhere else (for some reason Colombo, Sri Lanka always comes up; so does Cairo).

- Think about what you'd like to use the miles you earn for later. A round-trip redemption on miles I earn on my program, Aegean's Miles and Bonus, costs 25000 miles within the Asian region, be that flight from Tokyo to Osaka or Tokyo to Bali; this is good value for me since I live in Hong Kong. But is that good value for you? I'm happy to call Greece; other people want the convenience of instant redemption bookings online.

I cobbled together a route on the calculator you linked, but didn't price it out flight by flight, that was something like New York-Lisbon-(break journey, taking a train to Porto then back to Lisbon)-transit in Munich-Tbilisi-transit in Istanbul-(break journey and visit Istanbul)-Cairo-(train to Alexandria then back to Cairo)-transit in Istanbul-Delhi-transit in Bangkok-Luang Prabang-transit in Bangkok-Taipei-Tokyo-Auckland-Vancouver-New York.

That's 15 nonstop flights, and if you cut out Auckland and Vancouver and replaced Luang Prabang with Singapore you'd save a few flights/miles; it may actually be impossible to do all this in three weeks. You'd get to fly in business class on every route except Thai Smile's services to Luang Prabang, which might not offer a business service.

A more sane itinerary would be something like a red-eye New York-Lisbon-transit/visit Istanbul-Delhi or Mumbai-Singapore-Tokyo, and then back to New York. You'd still have a comfortable ten days-ish of on-the-ground time in Lisbon, Istanbul, an Indian city, a southeast Asian city, and an East Asian city, plus enough time to relax in business class lounges, not worry if your flight is delayed, and maybe be flexible enough to take the next day's flight if you want to stay a day longer. The last sectors would be on EVA Air, Asiana, Singapore and/or All Nippon Airways, all of which offer very polished business-class products for people used to the US airlines.

The best time of year to do this trip, I think, would be early spring or late fall (now would be good, actually!), though Thailand/mainland Southeast Asia would be absolutely roasting in late March/early April. You'll want to dodge the worst of Asia's typhoons and the desert heat of Cairo!

Good luck!
posted by mdonley at 9:53 AM on November 3, 2016 [1 favorite]

One benefit of a RTW ticket was as a relatively cheap way to get to very out-of-the-way places. Granted that you'll have several connections for these, but when else will you ever get to visit Svalbard (Home of the Polar Bears)? Two days is probably the right amount of time for many of these anyway.

Here's some places that fit that mold and are Star Alliance stops:
- Longyearbyen, Svalbard, Norway
- Ulanbatar, Mongolia
- Papeete, French Polynesia
- Mauritius in the Indian Ocean
- Galapagos Islands
posted by John Frum at 10:44 AM on November 3, 2016 [2 favorites]

posted by ibakecake at 11:43 AM on November 3, 2016

Kathmandu. I think you can hit the Monkey Temple and Durbar Square in 1-2 days and then head out to Pokhara, which all the Nepali folks in KTM recommended that I do instead of spending a week in the city.
posted by so much modern time at 11:46 AM on November 3, 2016

Boston. It's got some interest but after more than 2 days it's just more of the same.
posted by Miko at 7:15 AM on November 4, 2016

Dublin. San Francisco. Auckland.
posted by sideofwry at 8:54 AM on November 6, 2016

In the US: New Orleans.

Outside the US: Edinburgh.

I think you need to find a place that is a) small enough that most of the important stuff is within walking distance, or at worst a short cab ride, of each other, b) has a limited number of big-ticket sights, and c) has charms and culture that are immediately apparent, and easy to digest. Other possibilities include Quebec City, and perhaps Seville.

You could spend more than two days in most of these places without getting bored (maybe not Quebec City), but you could certainly cover the big stuff in two days while still having some time to relax and wander around, and leave with the sense that you've gotten a feel for the place.
posted by breakin' the law at 8:16 AM on November 8, 2016

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