How to Plan a Trip (and Feel Somewhat Organized)

Hellooooo and welcome to another day of travel tips with me!! I got a lot of planning and finance-related questions from your comments on social media, so I’ve broken it up into two days so I can answer it all the best I can! Today we are focusing on my planning process and what works for me. I’m going to start out by saying that I am very right-brained (creative and all over the place) and that I am the most disorganized ORGANIZED PERSON that you will ever meet. This is the system that works for me and I am going to show you actual documents that I am currently using to plan our trips for 2020 so far!!

My trips fall into one of two categories:

  1. I fall in love with the idea of seeing one specific thing in a city/country and then plan the rest of the trip around that. One example is when we went to Okinawa (the “Hawaii of Japan”). Mase and I love aquariums and found out that one of the biggest ones in the world is on Okinawa! I didn’t know anything else about the island, but I found more to do so we could see that one thing. We discovered some amazing beaches, historical sites and museums along the way, but I never would have gone without having seen that aquarium!
  2. I fall in love with the idea of a city/country in general, and later find specific things to see and do. I think that is how a lot of our trip to China was; it was a place that was so different and foreign to me and I was so intrigued by its culture, especially after studying parts of it in art history classes. I didn’t have one specific thing in mind that I wanted to go to China to see, I just wanted to experience the country itself. We ended up going to panda sanctuaries and camped on the Great Wall and wandered through golden temples, but none of those were the driving force to go on that trip.

Once I decide where I want to go, I start brainstorming. I will start a document on my computer with all the things that I would love to do on this trip. if you know me at all, you know that I am not the biggest fan of tourist attractions. There is a reason that the tagline of my blog is “travel like a local”! My goal with every trip is to gain a better understanding of the culture, the people, the language, and just what LIFE is like there. I don’t want to have the same experience as every other tourist who visits that city; I want to feel like my experience is unique and gives me more understanding on how to empathize with people.

A lot of you wanted to know how I find places to go on my trips, so I’m going to make a quick list of my go-to resources for authentic experiences around the world!

Resources for authentic experiences and travel inspiration:

  • Pinterest! I have started to break my travel pins up into parts of the world, such as “europe”, “asia”, “south america”, etc. When I start planning a trip to Chile for example, one of the first places I’ll go is to that board. Then I’ll repin the posts about Chile on a different board that is dedicated to this particular trip that I’m planning.
  • Another obvious answer… Instagram! People on Instagram are so creative and inspiring and I love that we can connect with people from all over the world with all different experiences so we can share them with one another! I use Instagram basically the same way I use Pinterest. I have a Europe board and a South America board and so forth. When I see a post of a place that I’d love to visit someday, I always save it for future reference! That way, I already have a lot of information saved before I even plan a trip. I personally love Sage Stephens and Zoelaz.
  • Travel blogs. Of course! A few of my favorites are The Blonde Abroad, Aggie, HBGoodie, Tara Milk Tea and Leonie.
  • Travel advisor. You can search top things to do in almost any city in the world! I love to read people’s reviews and advice about buying tickets, transportation, and overall experience at any place.
  • Google. If you type “things to do in ___” it will come up with a lot of good ideas. This is also a great way to find
  • Airbnb Experience. Their platform isn’t just for places to stay anymore. They have experiences led by locals in cities all over the world, ranging from bike tours to photoshoots to personal shopping trips to food tours of the city’s cuisine. I haven’t done one personally yet, but I have heard amazing things!
  • National holidays & festivals. I always make a point to search for the national holidays and festivals of the country I’m visiting to see if we can adjust our trip by a few days to make it or plan to experience any cool local events. There is NO WORSE FEELING than flying into Hong Kong 2 hours after the Chinese New Year festival ended. I have learned this one the hard way too many times — doing your research pays off!!
  • I’ll add one more resource to your list… yours truly. I love answering questions so leave me a message or comment on this post or Instagram!

Getting Your List Organized

Now that we have brainstormed some things that we want to do, it’s time to get a little more organized. I usually start by looking things up on my map and grouping things together by location. If it’s a big space, such as an entire country, I will usually do this process twice.

Below is a screenshot of a trip we did a couple of years ago (China) and a screenshot of a trip that I recently started planning (Paris). For our China trip, we knew we were going to the country but not necessarily what part we were most interested in seeing yet. I listed out random things in China that I had found through the resources listed at the top of this post and then went on to group them into the north, east, south, or west side of the country. Then I broke it down even further once we had decided which side of the country we are going to. I am also currently using this process for our Paris trip this fall. I don’t want to spend a lot of time traveling back and forth, so I plan which things we will want to do on the same day because they are located close together. You can see that I’ve identified what is located on the (east), (north), etc. sides of the city so I know which things to do on the same day.

*Note: as you can see, I like to include links so I know where to buy tickets or get more information!

Find Your Prices and Formulate a Budget

We have a pretty solid plan so far! Now let’s figure out the details. At this point, I’ve usually been gathering links to buy tickets and pricing information along the way, but this is where I comb through it all to make sure I have all the info I need, including how much all this is going to cost so I can be prepared. I’m still in the process of planning, but here’s a screenshot of where I am at so far with my Paris plans coming up:

* I am writing a lot more about planning for a trip financially in tomorrow’s post, but this is starting with some basics!

The Last Step: Making Your Itinerary

At this point, I take my grouped “things to do” and schedule them out day by day in an itinerary. This is so important because :

  1. You don’t want to wake up one morning in Puerto Rico, look at your itinerary, and say “shoot! I don’t know what else to do for these last 2 days!” I speak from experience.
  2. This is also a great time to assess how long or short you want your trip to be.

Matching things you want to see/do to how many days you have is like trying to match your cereal to milk ratio — it’s almost impossible to get it exactly right. I think it’s also important to find a good balance between planned activities and time to be spontaneous! You don’t want to have a rigid schedule or you might miss the once-in-a-lifetime festival going on right down the street, but you also want to avoid having absolutely no direction for an entire day. It’s all about balance.

Sometimes I’ll see that I only have activities planned for 5 days for a 9-day trip, for example, in which case I’d go back to step 1 to find more amazing things to do. On the other hand, I’ve also had too many things that I am dying to do, so I decided to extend our trip by a few days to have time for it all. You just don’t want too many unexpected surprises and have to miss out on something you were counting on!

Last comment on this topic — DO make some time to be spontaneous! On some itineraries, I’ve even ordered things from most important to least important. That way, if we don’t have time for everything because we discovered something along the way, I know I made it to the most important things on my list.

Hope this helps you plan your next trip!!

xx

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