Sean and Mittie | To Plan or Not to Plan: The Question 9

To Plan or Not to Plan: The Question

To most people, the idea of having a planned trip is essential. Arriving somewhere with a set idea of where you’ll stay and for how long often feels necessary to relaxing and enjoying your trip. But what if you left some of those plans open ended? How would it change your experience of the place?

The decision to plan or not plan a trip is different for each person. Here’s a brief guide to finding your travel equilibrium.



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It’s hard to know what something will be like from afar. Though research and recommendations help inform your decisions, you never know till you get there. What if the place you were recommended isn’t the right fit for you? What if the destination you’ve landed in is mediocre, or worse, you’re not enjoying it at all? When your travel schedule is flexible you can test the waters before deciding how long you want to commit to a place. Having hotel reservation for the duration of the trip isn’t advisable, unless its high season or you’re 100% sure of your destination. Otherwise it can limit your possibilities.


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Last minute changes in plan can be of the necessary variety, which may leave you changing a plane ticket and paying for it or stuck in limbo because of lost luggage, or they may be more of the spontaneous variety, like hearing a great recommendation and choosing to follow it. Either way, too tight of a travel plan can box you in, leaving you unavailable to take opportunities or go with the flow. One of the best travel experiences, in my opinion, involves spontaneous decision making based on recommendations and ideas on the road.


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When you’re plans are flexible you can connect more deeply with local people, take advantage of opportunities to follow their suggestions, eat at their tables, stay at their homes, or embark on a completely unexpected adventure.  These things can and will happen, if you allow enough flexibility in your travel schedule. Often pre-planned hotel stays and packaged tours offer non-authentic cultural experiences, leaving you without the true taste of the culture or destination.



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Planning means a sure place to stay and transportation leaving at a certain time on a certain day. I recommend planning the travel to and from the region, but not within the area, and booking transportation similarly. The major exception is if you are traveling somewhere to a large scale event, like Day of the Dead, or during high season (think beach during spring break). During average travel conditions, the worse-case scenario includes delayed travel dates or times and the need to get creative with housing, which may result in a house stay or camping. If the plan is flexible to begin with, changing plans by a day or two won’t matter, and you may have the opportunity to experience something new and unexpected.


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Of course, we feel safer with a plan. Whether it makes us any safer depends on the destination and type of experience we’re seeking. By planning the arrival and departure transportation and lodging, we feel confident to arrive, take stock and plan from there. It’s important to research the areas to be avoided in any location, avoiding dangerous zones, and planning ahead when entering potentially dangerous situations. It’s also helpful to share destinations and dates with friends, in case the unexpected were to occur.

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To determine your ideal travel planning style, consider each of the elements above in relation to where you’re traveling, how long you’ll stay, and whether you plan to move around the region or stay put. Generally, the longer your trip, the more exploring you’ll be planning to do and the more flexibility you can afford in the planning. Shorter trips and trips to a specific city or town don’t require as much flexibility as your home base won’t be changing, or if it does, it will be minimal.

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For example, a month in Guatemala during low season and with a car meant the possibility for many destinations, many routes, ample time to get around, and the ability to capitalize on any opportunity that came our way. We planned when we would leave San Miguel de Allende and the first destination in Guatemala, but little more. Beyond that, we listed out the places of interest and brought our trusty atlas. A month in Cuba, on the other hand, required slightly more planning. We had our flights in and out, and an ordered list of places we wanted to see with speculative dates, as well as intended transportation. We didn’t reserve any rooms or buses in advance, however, which was smart since there was so much delay in getting anything done there. We were able to be flexible without losing money from canceled tickets, etc.

What kind of balance works for you when it comes to planning a trip? Do you prefer more planning or less? Why? Please share your comments below! 

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