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An Indecisive Traveler Decides Where to Travel

My website name is very fitting. Even though I have always been a meticulous planner and an organization enthusiast, I always struggle to make decisions. Whether it be what to order for lunch or where to travel – it’s just a real problem for me.  I left Argentina and moved back to the US earlier this year for many reasons. One of those reasons was so that I could travel in North America more often. In case you haven’t noticed, North America is a big place. I’ve gone on a few trips already this year, but I always had friends in the locations, which made the decision pretty simple. The problem came when planning a trip with my boyfriend, Pedro.

Too much flexibility is a bad thing

So free! So lost!

Now that I am a freelancer, I can take off basically whenever I want and go wherever I can afford. That may sound wonderful, but it actually made planning a vacation rather difficult. At first, Pedro and I were planning on going to Puerto Rico, where he is from. However, in the end, we decided that would not be much of a vacation for him, so we began looking at other options. We moved on to New Orleans, then Miami, then New York, then back to New Orleans…but maybe Miami? We couldn’t decide.

All of the cities on our list sounded great. They all had their pros and cons. We could drive to New Orleans – fun road trip! Miami is close to some of his family and may be somewhere we want to live someday – a chance to preview it! I’ve never been to New York – crossing a must-see destination off my list! Then came the cons. Driving to New Orleans would take an entire day there and another back. We have already been to Miami once. New York is expensive. The pros and cons lists always left the cities more or less even. We really wanted to take our vacation in August and time was running out. We couldn’t book hotels, flights, or plan activities if we didn’t have a destination!

We chose New York

Honestly, since we had been to Miami before, we kind of knew it had no business being on the list. As for New Orleans, as much as we both want to see it, it’s a Southern summer there right now, and compared to New York, there shouldn’t be much contest. The whole time, I was just worried about money. I kept checking prices on flights, hotels, activities, and food in all of the destinations. I wasted my time stressing over three hypothetical vacations instead of one real one. Once I said the words “I want to go to New York” aloud, I was able to focus my excellent research abilities. Within the day we had found amazingly cheap accommodations. Within the week we had found an incredible flight deal. We planned some activities and started getting really excited. We even realized that we had booked the trip over out 1 year anniversary without even meaning to. Everything fell into place.

Oh New York, I can’t wait to meet you! Photo Credit: @Travelyourself

So here’s my tips on deciding where to travel

  • Don’t be too flexible. Having a thousand options is not going to make choosing very easy.
  • Narrow your options down to 3-5 locations.  Think about your choices for a few days. Try to see if one of them pulls at you more than the others at this particular time.
  • Go with your gut. If one of your options is the one you want most, go with that one. Don’t over think it.
  • If you still can’t decide, pick something trivial. Do you know someone you could meet up with in one of the cities? Is there a particular thing you want to see in one of those places? Choose your location based on that single thing! You’ll find other reasons to be there.
  • Pick a city first, plan the rest second. – The problem with having multiple cities on your list is that you try to plan whole itineraries for each one. You begin comparing flight and hotel costs, weighing activities against each other, and all other sorts of nonsense. Let’s be real here-  if the city is on your list, it’s probably worth visiting. You don’t need to convince yourself of that. What you need to do is decide where to travel this time. Like I said in the last point, you can just pick one thing. If you find an awesome flight deal to one of those cities- perfect. If an awesome event is going on in one of them – go there. There will be other vacations. Choose one city now and plan accordingly.

I don’t think I have cured my indecisiveness when it comes to travel (which is kind of a good thing, because I’m can’t change website again) but I definitely took some baby steps towards learning how to decide. I’m am thrilled that Pedro and I are going to New York together next month. I am going to eat from food trucks, go to awesome museums, possibly convince myself to shop even though I hate it, and use my people weaving and speed walking skills on the busy sidewalks. Take that indecisiveness!

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