In many ways we are all different. We have different interests, different histories, different ideas of fun and different expectations for ourselves and the world around us.
Yet, at the same time, we are very similar at the core. We want to find happiness, we want to be fulfilled in life, we want connections and love, and when we travel, we want it to be great.
So, how do we have great experiences traveling? That road map can vary from person to person. There are many excellent guides out there that give advice about how to travel, where to go and what to pack. But they often make the assumption that all people are alike, and want the same thing. This isn’t necessarily bad, as long as those reading the guides don’t take it as a 100% right answer.
Unfortunately, there is no right answer. It all depends on what you want. There is a recurring theme of all guides telling you to pack as little as possible, and typically I agree with that, especially if you are newer to traveling. Start with less than you think you need. But, like everything, that doesn’t necessarily work for everybody.
I once traveled with a friend who carried a massive backpack, twice the size of what I travelled with, and he was absolutely content with it because he always had everything he needed. He had all his little gadgets and things that made his travel experience better. My back hurt just looking at it, but having all of those things brought him comfort.
I have also travelled with people who have lived with a small 20L backpack for years and were happy living as simple as possible. Neither is right or wrong, you just need to discover what makes sense for you.
This article attempts to help get you closer to understanding what you may want and need before you get out on the road so that you can travel in a way that works for you.
For example, if you are the sort of person that likes to be in control and have all aspects of your life organized down to the tiniest detail, you probably aren’t going to enjoy showing up in a new city on the other side of the world, where you don’t speak the language, and you haven’t booked a hotel or researched anything at all. But for some people, that is the exact experience they are looking for, and to travel with everything booked months in advance will make them feel trapped and restricted.
Before you plan a trip, no matter how big or small, you can set yourself up for success and be more likely to have an experience that aligns with your personality, interests and expectations. Just because it sounds badass to land halfway around the world with no plan doesn’t mean you will enjoy doing it.
I have traveled very spontaneously, with minimal planning, and I have traveled with things booked in advance with less room for improvising. I get enjoyment out of both, and I’ve had good and bad experiences with both.
For who I am and what I enjoy, there is a time and place for both types of travel. I am pretty easy going, and an experienced enough traveler to go with the flow when everything turns to shit and you have to improvise and hope for the best. But sometimes people panic or breakdown, and while sometimes it’s unavoidable, sometimes it is avoidable.
In 2011 I was backpacking through Peru, Bolivia and Chile for two months, where the only accommodation my girlfriend and I had planned was for our first three nights in Lima. We had a general route in mind, and I had a return flight out of Antofagasta, Chile, but everything else we would figure out as we went.
The second day into the trip I got the worst stomach bug of my life. I could barely move, was vomiting and had diarrhea all day. I couldn’t even drink water without it coming up 10 minutes later. Because we didn’t have any hotel, tour or plane reservations we were able to extend our stay in Lima a couple days until I felt well enough to travel what would be an almost 24 hour bus ride to Cusco.
I felt awful on that long bus ride, and clutched a bag to vomit in the whole way, but I did survive. Unfortunately I was still sick for several more days in Cusco, but by having nothing set in stone we were able to change our plans so I wouldn’t have to spend a full day on a bus exploding from both ends.
After I had fully recovered and we went to Machu Picchu, we continued on to Puno, the largest Peruvian city on Lake Titicaca. After an eight hour bus ride we then had to trek around the city with our backpacks searching for a place to stay. Many of the places were all booked up and the few options left were pretty awful and overpriced.
Fortunately, my girlfriend is from Chile and obviously fluent in Spanish, so that helped not getting ripped off when asking around for prices in person (the less you seem like a foreigner the less likely you are to get ripped off). Yet, we still spent hours walking around trying to find a place before settling on an absolute dump.
It was one of those times I wished we had just booked something in advance, instead of wasting time and ending up with some place disappointing. Our plan was to spend a night on the floating islands on Lake Titicaca, which I highly recommend, and from there journey on to Copacabana, a small town on the Bolivian side of Lake Titicaca.
After our disappointment in Puno, we did a quick search for lodging on Hostelworld and found a beautiful place to stay called Las Olas. At about $40 USD per night it was a little more expensive than our budget allowed for, but it was way too cool to pass up, and also a great deal for what it was. It ended up being the coolest place we stayed the entire trip. In fact, I still think about that place frequently and fantasize about returning for an extended stay.
Those couple days taught me a valuable lesson about the time wasted searching for a place when you don’t have somewhere booked. Also, the likelihood of ending up paying more and getting less.
When you book ahead, even just a few days, you are at least aware of your options, how much things cost, and the best areas to stay in. So instead of ending up in a dump you can end up somewhere amazing, or least acceptable.
Tip: If you don’t want to book things ahead I still recommend doing a little research so you are aware of the options that exist and the general price range things fall into so you aren’t completely ignorant of the market. That being said, you may also be the sort of traveler that doesn’t care in the least about the quality of your accommodation as long as there is a place to rest your head.
I have stayed in enough crappy places that if I can pay the same price for something twice as nice, I tend to prefer that option. I’m also a sucker for good design and cool architecture, so I gravitate towards visually appealing places, and if it comes with free breakfast, even better.
As you begin to wonder how your personality and your interests will affect how you travel, ask yourself these questions:
Do you want to travel fast or slow? – Is it more important for you to see somewhere new at your own speed, without rushing? Or, do you want to see as many places as possible so you can say you’ve been to 4,358 countries? The experience you have in a city for 1-2 weeks will be way more in depth and relaxed than it would be in two days. You don’t get to know a city in two days. You don’t get to know a city in one week either, but you can experience and absorb significantly more.
Tip: I recommend no less than four days in a destination. It always goes too fast, especially when the first and last days tend to be travel days and you really only have two full days.
Are you relaxed and easy going? Or, do you get anxious if things don’t go your way?
What do you do when things don’t go your way? Are you quick on your feet and calm, or do you get stressed and freeze up?
Would you rather travel with only the bare necessities? Or, does it make you happy to be prepared for everything, and have little comforts that others may deem unnecessary?
Are you quick to adapt to any situation? Or is it hard for you to break out of your comfort zone and go with the flow?
Do you get FOMO (fear of missing out)? If you discover something new on your trip that you can’t do because of a tight schedule, will it bother you?
Do you like to discover random restaurants while you explore and are ok with the occasional bad meal? Or, do you prefer to do your research and make every meal as great as possible?
What is most important to you? A cool place to stay? Great food? great activities? Relaxing and taking everything slow?
Sit back and take a moment to live the following experiences in your head. Ask yourself how you would handle them, and how you would feel. Try to hone in on what you feel more than what you think. Many of us are guilty of wanting to believe we would handle all difficult situations with grace, but the truth is that maybe we won’t, and that’s ok. The more honest we are with ourselves, the better we can prepare.
Situation 1 – You arrive in a new city. You don’t speak the local language, you dont have a place to stay and as you start asking around you realize everything is booked up. After four hours of searching, you end up in an absolute dump in a neighborhood far from everything you want to do.
How do you feel? Do you care? Are you mad? Sad? Or will you have a beer and forget about it 20 minutes later? Do you shrug it off as an inevitable part of traveling, or do you curse the experience and feel like a fool? Do you get anxious going from place to place feeling like you won’t find a room at all? Will you ruminate about how crappy the room is for the next three days, or as long as there is a bed you don’t care?
Situation 2 – You have planned a month of travel across Italy. Every day is booked with accommodations, activities and even lists of restaurants. But you arrive for your four days on the Amalfi Coast and every day it rains, crushing your plans of boat tours, hiking and hanging out on the beach. Plus, you meet some locals who talk about this incredible party in the hills the day after you leave that only locals know about. And of course, the weather is going to be perfect.
Will you kick yourself in the ass for not being able to stay a few extra days? Or will you shrug it off and be happy moving forward, even though you didn’t get what you wanted out of the Amalfi Coast, and you are missing a once in a lifetime opportunity to do something cool and spontaneous?
Situation 3 – You packed for a three month trip across Southeast Asia as simply and lightly as possible. You are carrying around a backpack that is small and convenient. But you frequently find yourself needing things you didn’t pack. So you have to go out and shop for random items on occasion. But your bag is so small you have to throw out an item to replace it with what you just bought. Sometimes you can’t find what you need and then have to get by without things you typically would want.
Are you ok spending the time searching for those extra items you need, or do you not want to waste time doing mundane tasks? Can you sacrifice basic comforts in order to travel more simply, or do you prefer to have everything you need regardless of the extra weight you need to lug around?
Situation 4 – You are planning to travel around Europe for three weeks. It’s your first time there so you want to see as much as possible. You plan on eight cities in four countries having only 2-3 days in each place. A week into the trip you realize how little you can do and see in each place, especially when factoring in travel days and time spent on trains. You don’t have time to do most of what you want in each place and have to settle for rushing through a couple main tourist attractions. You find the constant moving exhausting as well.
It’s fun, but it all starts to feel like a blur. Is this style of speed traveling fun? Or would you rather have the time to see more in each place and get to see more of the local culture?
Having asked yourself these questions and figuring out what is important for you on a trip and the things that may or may not bother you, what does this all mean? Hopefully it can help point you in the right direction about:
What to pack for your trip, and what to leave at home.
Whether to travel spontaneously, book everything in advance, or something in the middle.
How much research to do, and how much to leave to chance.
How many destinations to visit on your trip, and how much time to spend in each place.
Where to focus your time and money – lodging, food, shopping, activities or a combination of everything?
Remember that not all travel guides apply to all people, and that by asking yourself questions about your personality, interests and expectations you can set yourself up for success in your adventures.
Just because most guides say to pack as little as possible, doesn’t mean you can’t bring that random luxury item that will make your trip more enjoyable. Just because it sounds cool to travel with no plans and live spontaneously doesn’t mean you will enjoy it. And just because it sounds impressive to say you have been to 245,956 countries, doesn’t mean you will know anything about them. But then again, if these are the things that make you happy, then by all means go for it. All I hope is that you find the way of traveling that works for you, because for me it certainly took some trial and error.
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