Trip Planning

Before we cross a border, Andrea and I always take at least a few hours to get our bearings and plan for the next country. Over the past several months, our methods have evolved, but here’s our process:

  1. Think about your goals. Before anything else, it’s helpful to think about why you’re traveling and what kind of experiences you’re looking for. A lot of people take vacation to relax and take things slow, but others are looking to shake up their regular routine and see lots of sights. Andrea and I tend to focus on cultural experiences, food, lots of walking, and a dash of adventure. No matter your goals, knowing ahead of time if you want to prioritize museums or bars will help you narrow things down later.
  2. Nail down a timeline. For us, this can be a bit tricky as we try to keep things open-ended, but it’s always important to know when and where your next commitment is. For most people, that’s a flight back home. For us, it can be a WorkAway commitment or a friend flying in to visit. In any case, your timeline and your ambition will determine how quickly you move between places and what type of transport you use.
  3. Learn the basics. We always check visa requirements, look up the currency and exchange rate, get a general idea for price level, research transportation options, understand the safety situation, and read a little of the history of each country we visit. We use the Triposo app, WikiTravel, and other travel blogs. Having this information at the forefront of our minds helps us make sense of what we see on the ground.
  4. Identify the highlights you can’t miss. Is there something you just have to see? If so, prioritize it and dig into logistics to make sure it happens. We don’t typically have a lot of big must-dos, but Machu Picchu is a great example of something you need to plan out in advance because tickets sell out. After all, it is one of the new seven wonders of the world and just about everyone else wants to go too. Make sure you carve out time and research logistics to make sure you don’t miss out on anything crucial.
  5. List out other destinations. We like to make a quick list of potential destinations and include notes about what each place has to offer and how to get there (roughly). We rely on other travel blogs, online guides, and word of mouth. From there, we try to divide our timeline up to give ourselves at least a couple of days in each place. We use Rome2Rio to get an idea for transport.
  6. Book a night in your first destination and go! For your first day on the road, it’s always good to know where you’re going to sleep. We typically compare prices between Hostelworld, AirBnb, and things we’ve heard from other travelers. After the first night, we keep it more flexible.
  7. Put your ear to the ground and ADAPT! Time and time again, Andrea and I learn that you just can’t beat local knowledge. You may have the best plan in the world based on your research, but you never know when you’ll meet a friendly bartender, a taxi driver, or a fellow traveler with better advice. Although it would have never occurred to us a year ago when we were counting up our precious vacation days and trying to cram as much fun into our days off as possible, we’ve come to enjoy travel improvisation. We still do our research online and learn about where we’re going, but we’re relying more and more on word of mouth and local advice.

It’s important to note that, much like the Pirate Code, these are more like guidelines and we adapt them to fit our situation. If we have a visitor or an upcoming flight, we’ll plan things out a little more due to time constraints. If it’s just us and we have nothing big coming up, we take it a bit more slowly and leave lots of room for improvisation. Learning to embrace that ambiguity and leave space for new ideas has become one of our favorite strategies and has brought us some of our coolest experiences.

  • When we were in Medellin, Colombia, we had planned to spend about two days in the city since we were on a pretty tight schedule to get to Quito, Ecuador and meet up with a friend. Our first day in the city, after a grueling night bus from Cartagena, we decided to stretch our legs and see Parque Arvi, which is an ecological nature preserve and archeological site just outside the city. We ended up on a guided hike through the park with a big group of Colombians and Venezuelans. Just as we rounded a corner in the path and a beautiful mountain lake revealed itself and one of the other hikers stopped the group and proposed to his girlfriend. The whole group whipped out their cameras and became a flurry of smiling, photographic energy. On the way back down the mountain, we all buzzed around them, congratulating them on their engagement. A big group of us made plans to have dinner and some celebratory drinks, so later that night Andrea and I found ourselves enjoying a delicious bandeja paisa surrounded by a new group of Venezuelan friends. We spent the next three days exploring Comuna 13, Boston Park, Nutibara Hill, the University District, and even the nearby city of Guatape with our “Medellin Parce” (Buddies). Meeting these friends was completely unplanned and our schedule flexibility allowed us to have a fantastic time with them.
  • When we first arrived in Costa Rica, we spent a couple days in the northwest of the country visiting an old friend in Liberia and getting our beach on. We knew we had our first WorkAway coming up in a week or so, but left ourselves a few free days before we needed to travel there just to see what would happen. One day we were sitting at Playa Tamarindo having a drink when two college friends walked up and sat down at our table! We hadn’t seen them in years, but they just happened to be at the same bar on the same beach at the exact same time. We’re always open to these kind of serendipitous encounters and spent the next several hours catching up, swimming, and swapping advice on places to visit in Costa Rica. Although we had planned to visit Monteverde the next day, we pushed those plans back to hang out with Connor and Becky. We all hopped into their rental car the next day and visited the Lomas de Barbudal Biological Reserve and a waterfall called Llanos de Cortes, where we got to jump off cliffs into big pools of water! Before running into Connor and Becky, we hadn’t even heard of the place, but it ended up being one of the big highlights of our time in Costa Rica!

Andrea and I have been on the road for about 7 months now and we’re constantly surprised by how plans shake out. Sometimes we can figure out exactly what we want to do through online research, but other times we throw all those ideas out the window and just take the opportunities that present themselves. We’re constantly re-learning to keep our minds open and our ears to the ground. The world is full of surprises and we receive them with open arms.


5 responses to “Trip Planning

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