Where Should I Go On Vacation?

I try to get out of the country at least once a year, and I haven’t been out since last summer. So, I’m thinking about a trip for two weeks in late October or early November, but I don’t know where I want to go yet. Help me decide!

I’m only going for two weeks, and I want this to be part relaxation and part exploration, so I don’t want to try to cover too much ground. I also don’t want to go anywhere I’ve been before, which rules out most of Italy, Southern China, Laos, Cambodia, Vietnam, Malaysia, Morocco, and Amsterdam. Other than that, I’m game to go pretty much anywhere. Here are a few on my shortlist (really leaning toward the first two):

  • Prague
  • Barcelona
  • Bogota
  • Lima
  • Costa Rica
  • Croatia
  • Greece

Where do you think I should go? Open to destinations not on my list.


  1. Barcelona.
    Costa Rica.

    Haven’t been to Costa Rica but heard it’s beautiful (my family has been there).
    Barcelona I’ve been to. I would love love love to go back. Great food, great sights.


      1. Thanks!

        I really want to go to Lisbon, but since it’s become the “new San Francisco” for Automattic, it’s possible I’ll get to go to a work meetup there sometime.

        I’ve always wanted to go to Barcelona. That’s high on my list. Costa Rica, too, but I feel like Costa Rica is more of a holiday destination for Americans and now that I live in the Southwest, I suspect I might have opportunities to go with a group at some point.


  2. Barcelona – I would combine with Madrid – Madrid is totally underrated and has so many amazing museums and great culture and neighborhoods and you can do great daytrips out of both cities (Segovia, Montserrat, Girona…). Should be good weather and two weeks will be jam packed but you will get a good sense of both places and get to stuff your face with awesome food at very reasonable prices.

    Prague – meh. too touristic and kind of unfriendly. I’ve heard much better things about Budapest and Krakow if you are in the mood for Prague-like ambiance without the Disneyfication and disaffection and crowds.

    Bogota – honestly, a dangerous dump and nothing much to see. some of the other stuff in Bolivia is cool and I can give you awesome tips if you are going to do Bolivia but I wouldn’t go alone. I was strangled and left unconscious in the street in Copacabana (Bolivian side of Lake Titicaca) and I heard of lots of people this happened to all over Bolivia – in broad daylight, even to not solo travelers, etc.

    Lima – if you are going to do Peru, then do Macchu Pichu and Cusco and Ollantaytambo. Similar issues as Bolivia though in terms of stranglings. I would combine the two countries at some point when you have more than two weeks.

    Croatia – really best to do as a sailing holiday 😉

    Happy to discuss any of the above – just call Sumi…


  3. You mentioned Prague and Barcelona, but 2 weeks in each of these cities is too much I think. Plus the weather is not that nice in Prague at that time of the year.

    Greece is a nice idea; the weather will be better there, and you could get to go around a few islands during the 2 weeks, I’d vote for that!


    1. Good call on the weather, I always forget to think about that. 😛

      I’m more worried about doing too much than too little, because I have this idea I’ll spend some of the trip writing.


    1. Yes, I do really want to go to Istanbul, but I went to Morocco last trip, which is rather similar architecture, etc. So, I think I’ll save that for next year. 🙂


  4. I went to Bogota about 10 years ago; it was very nice, and I hear that it’s even nicer now, cleaner and organized.

    As for Barcelona, that’s high my list of future meetup destinations, but you won’t get to see as much on a meetup compared to going 2 weeks by yourself.


    1. True – I never want to “waste” personal travel on somewhere I might eventually get paid to go, but it’s true that work meetups don’t leave as much time for heavy exploration. 🙂


  5. I’d say that if you’re considering Spain that you skip Barcelona and head to the South. Cities like Granada, Sevilla, and the “white towns” like Ubrique and Benocaz is where the real Spanish culture is (in my opinion.)

    Barcelona is really nice, but it’s more like a European city than a Spanish one.


      1. That’s because Spain is the best. If you need to bring a translator, I’m happy to come in exchange for food and lodging. And beer. Just putting that out there. . .


    1. Ignore what Alx said and go to Barcelona. Best city in the world! 😉 And you can take side trips to interesting places like Girona, Cadaqués, Montserrat, …

      But really, it does depend on what you’re looking for in your trip. I’m sure you won’t be lacking for ideas on what to do, wherever you decide to go. 🙂


  6. I actually just wrote you about WordPress support, then came across this by clicking your display name. (Sorry to mix business with pleasure). I did just come back from Spain though, so I thought I’d comment…

    I did a much shorter, one week trip. Barcelona for a few days, followed by a cross country drive (5.5 hrs nonstop) through Olite and Pamplona to San Sebastián. Barcelona was a great city for food, culture, and architecture. San Sebastián is great for a more relaxing beach scene in a beautiful small town. Much less to do than Barcelona, but LOTS of charm. Loved it. Hope that helps! 🙂


  7. I think you’ll have to go to NYC for an obligatory bachlorette party and shower. It’s your damned coupled friends ruining any possible moment of singleton joy.
    (Does your tumblr still exist?)


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