How I Choose My Destinations & Prepare For Each Trip

How I Choose My Destinations & Prepare For Each Trip

By |2016-07-01T15:34:52-04:00June 12th, 2013|Travel Tips & Advice|35 Comments

Choose My Destinations

How do you choose your next destination when you have the ability to choose almost anywhere in the world? Then, once you decide where to go, what do you do to prepare for your travels? And finally, for those who don’t have a limited number of days for their trip, how on earth do you decide how long to stick around each place you visit?

The above questions were asked in the comments section of my last post when I asked all readers of the blog to specify what you want me to write about. They are great questions because, if you’re planning on spending a significant amount of time traveling the world, you will have to answer them over and over again. And since I’ve needed to ask myself these questions all the time over the past 14 years as I’ve moved around the world from place to place, always trying to figure out where I should go next, I figured it would be a good idea to provide my answers in a post.

Let’s begin…

Choosing a Destination

Very rarely do I know where I’ll be more than one month in advance. I’ve never been much of a planner and with the current lifestyle that I’ve carved for myself, it is almost impossible to make future plans without having to change them once, twice or several times.

So, I don’t plan.

I prefer to use that simple method of ‘going with the flow’, making decisions last minute whenever I feel the inspiration or need to move on to a new country. Sometimes I’ll choose to visit a country because of something I read recently, other times I’ll choose based on something I want to learn or people I want to see. All I know is that if I were to wake up tomorrow with this burning desire to traverse the remote plains of Mongolia as soon as possible, I’d start looking for flights…and chances are I’d be in Mongolia relatively soon, even though the thought of going to Mongolia was nowhere to be found in my head today.

Choosing my next destination really is quite random for me.

With that said, I do believe that traveling must have a purpose. Without a purpose or goal, traveling can get boring quite quickly (hard to believe but it’s true!). As a result, I try not to choose destinations just for the sake of seeing a new country. Instead, I choose destinations because there is something I want to do there, some goal I want to achieve.

An example would be my recent trip to Yemen. That trip materialized in about two weeks after the thought of really visiting Yemen came to mind. And my reason for going was to visit a country that sees very few visitors so that I could hopefully shed even a tiny bit of light on this land and its people. I also wanted to visit Socotra Island because I had a feeling that it would be an incredible place to organize a Wandering Earl Tour and of course, I wanted to see it first-hand before organizing such a trip. (And yes, I’m still working on the details of that tour. Should be finalized very soon!)

Again, purpose. Travel needs a purpose. This doesn’t mean that you need to spend years thinking of some grand goal you’d like to achieve and which country would be the most ideal for you to achieve that goal, but having a goal, any goal, in mind certainly helps narrow down your options. I certainly wouldn’t go to China in order to learn Spanish and I wouldn’t go to Mexico to learn about European history.

Think about your interests in life and that will help you choose your travel destinations. Do you want to learn a language? Do you have friends somewhere in the world you want to visit? Is there a particular sight you’ve always wanted to see with your own eyes? Do you prefer to spend some time surrounded by nature or in a big city or on the beach?

Ask those kind of questions, which is what I do all the time, and deciding where to go next won’t be as daunting of a challenge.

Preparing to Visit a New Country

This is an easy one for me because I really don’t prepare much at all. Since I do choose my destinations at the last minute, I just don’t have time to do much research before I land somewhere new. And since I no longer use guidebooks (nothing against them, I just prefer to travel without them these days), I typically land somewhere knowing very little beyond what I already know just from being a traveler who is interested in the world in general.

If I know of a travel blogger who has recently been to the same place, I might check their blog or send them a quick email before I begin my trip in the hopes of finding some good recommendations, maybe for a place to stay or perhaps a location/experience that was particularly memorable. And on occasion I’ll head over to the WikiTravel page for the city I’m landing in and have a quick read, maybe to get a list of a few budget hotels to check out when I arrive. But that’s about it.

Overall, the reason I prefer this type of minimal preparation is because it allows me to travel with as few expectations as possible. If I don’t read a ton of stuff about where I’m headed, I feel that I’m more open-minded as I travel around. Filling my head with too many details, stories, news articles, etc. before I arrive would diminish my ability to treat every moment without prejudice.

On the other hand, doing almost no research can often lead to a longer adjustment period upon arrival. I will certainly need more time to figure out ‘how things work’ and there will be more surprises along the way, some potentially unpleasant. It can be a harder to find accommodation, find places to eat, learn how to get from one point to another or anything else you need to do while traveling if you need to learn it all as you go.

My recommendation is to do what you are most comfortable with. And if you’re just starting out traveling, definitely do some research before visiting a new country. I certainly did when I first started out. I had a guidebook in hand almost everywhere I went for the first few years. Then, once you become more experienced, you won’t feel the need to rely on a guidebook as much because you’ll have gained a travel confidence that is hard to explain until it happens. Strange situations just won’t seem strange after a while and the fear and worry that you once had when traveling to new destinations will eventually disappear, leaving you feeling as if you don’t need to conduct as much pre-trip research as you once did.

Brasov, Romania

How Long Do I Stick Around?

Deciding whether I should stay in a particular country for a day, a week, a month or even longer is, unsurprisingly by this point, something that I also don’t plan out in advance. As I seldom have somewhere to be, I am able to just show up and see how things go. If I enjoy a town, city or country, I stick around until I’m ready to see something new. If I don’t enjoy a place so much, I move on much sooner.

However, these days, I am not the same traveler I was in the beginning when I would strap on my backpack and set off for months at a time in a particular region of the world. Now that I work online and have things I need to get done in order to earn a living (more details on this in a future post), I can’t keep up that same pace. I need to travel slowly at times so that I can get things accomplished and sometimes slowly even means staying in one destination for a few months or more.

So, what I started doing (when I first began working online) was alternating between periods of normal backpacking where I would visit a few countries for a couple of months and periods when I would stay put in one particular destination for a month or two. This allowed me to continue working online, to put some real energy into this blog and to still see more of the world in the process.

It also helped keep my costs down because whenever I do stay in one place for a longer period of time, I am able to rent an apartment quite cheaply, making it much less expensive than staying in a private room at a hostel, guesthouse or budget hotel.

Eventually, though, my travel style changed once again and became what it is today. Now I prefer to have a long-term base, a location where I can really be comfortable and somewhat ‘settled’ while also being in a convenient location so that I am able to jet out for weeks or even a month or two at a time to new places. This ideal setup allows me to create stronger friendships, gain a deeper understanding of the local culture and of course, get more work done while at my ‘base’. I also have a comfortable and familiar place to return to after spending some time away.

The first place I used as a long-term base was Playa del Carmen, Mexico and now it’s been Bucharest, Romania for the past 18 months. I’m still traveling all the time but having a place to return to, a place where I can leave my stuff, has made a huge difference in helping me maintain my excitement about this traveling lifestyle. It’s just too difficult to build a blog and to really work on anything while constantly moving around the world from new country to new country.

How did I end up choosing Bucharest? It was actually completely unplanned. I showed up in Romania towards the end of 2011 as part of a Eurail trip I took around Europe and my plan was to stay for about 10 days before moving on to Bulgaria and Istanbul. But after a week in Romania I had met such wonderful people and had really enjoyed every place I visited that I simply made a sudden decision to stop and throw down my bags for a while. And I chose Bucharest because that’s where most of the people I met were living.

I certainly never imagined that I would end up spending so much time in Romania but that’s the beauty of travel – there’s always surprises and you never know what will happen once you cross the border into your next destination!

Any questions about choosing a destination, preparing for a destination or deciding how long to stay in one place? Let me know in the comments!

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  1. Karina August 15, 2015 at 1:48 am - Reply

    Hi Earl!
    Soy husband and I have been living/working in Australia for 5 years (New Zealanders so need for a visa lol) but after many overseas “holidays” we now want to do something a little longer/more permeant, but seeing as we are both over 30 working holiday visas are out of the question now…looking at Costa Rica for a month and Mexico for a month (at least/approx times, longer is better of course lol) and really
    Just need some inspiration on these destinations…any advice would be great!!!
    Regards from an avid travel dreamer

  2. Michael November 18, 2013 at 11:07 am - Reply

    I’m getting ready for a extended travel and have almost no plans beyond Thailand then boracay. I always get worried that I will not find a room where ever I’m going. I feel the need to book at least a couple nights in my destination before arriving. There lies the problem of where online to book my stay and all I read is horror story’s of people who book and lose there money with no reservation being booked… I will be traveling with my fiancé as well so that exasperates my worries. Can you maybe shed some light on whether to book ahead a little and maybe what website to use? (I’m going to boracay for New Years and am still having problems booking a room as they seem to all be booked or the website seems sketchy to book with….)

  3. Chancho June 27, 2013 at 11:47 am - Reply

    Hey Earl, in 3 weeks I leave for Guat and then travel overland to Mexico to stay for at least several months! I have the same Redwing 50 as in your airport picture above… do you carry 2 bags now? I ask because it looks like I’ll have to take a separate backpack for my laptop and a few other things. Should I just make sure to always have my little backpack on my person (planes, buses, etc.) during travel days? I’ll have the laptop locked in the Kelty when I’m settled in a spot.

    Love your blog and I’ll let you know in a few months if your apartment saving tips work for me in Guadalajara. That was an awesome post, man!

    • Wandering Earl June 28, 2013 at 4:18 am - Reply

      Hey Chancho – Everything I travel with does fit into my Kelty 50 but when I’m on buses or trains or taking a flight, I put my valuables in my daypack and carry that with me at all times. And then, once I arrive, I often put that daypack inside my Kelty and carry it all together.

      Enjoy Guadalajara!

  4. Jonas June 25, 2013 at 1:25 pm - Reply

    Almost booked a ticket phew.. . What countries would you recommend then in terms of making money so I am sure NOT having to go back home(my BIGGEST FEAR!).

    Thank you so much once again Earl it really means allot


  5. Jonas June 24, 2013 at 4:58 pm - Reply

    Almost booked a ticket phew.. :P. What countries would you recommend then in terms of making money so I am sure NOT having to go back home(my BIGGEST FEAR!).

    Thank you so much once again Earl it really means allot 🙂


  6. Jonas June 22, 2013 at 2:07 pm - Reply

    Regarding being actually able to stay there for as long as I want(jobs), which one would you choose of the two:)?

    • Wandering Earl June 23, 2013 at 6:08 pm - Reply

      Hey Jonas – Well, finding work in Mexico is not easy in any location, simply because it is a developing country after all and as a result, the jobs go to locals. But I guess Mexico City, simply because it is a massive city of 20+ million people, would provide more opportunities overall if you are able to find some work.

  7. Alex June 19, 2013 at 6:03 am - Reply

    Hi Earl,

    I’ve read your blog a few times and it is very interesting. Just found out that you are now in Bucharest so i was wondering if i can buy you a beer some time. I would really like to have a face to face chat with you. Please let me know if you are available. Thanks

    • Wandering Earl June 20, 2013 at 8:55 am - Reply

      Hey Alex – Sounds great…send me an email through the contact link above and we can make a plan!

  8. Julie June 18, 2013 at 7:47 pm - Reply

    OMG, I am such a Planner! Down to the nat’s ass, as they say. I leave NOTHING to chance! I want to know the when, the where and the how, so I can enjoy everything to the upmost! Planning my next trip is a lot of what I enjoy about traveling. Planning gives me the confidence I need to travel and know I am ready for anything.

  9. John Mayson June 17, 2013 at 12:18 am - Reply

    Crazy question. The backpack in that picture, the one on the ground. Is that the same on you mention here? namely the Kelty Redwing 50? I’ve been looking for a backpack like it, but I’ve had trouble identifying it.

    • Wandering Earl June 17, 2013 at 9:57 am - Reply

      Hey John – Yes, that is the Kelty Redwing 50, the new one that I mentioned in that post and I still love this pack!

  10. Terry Cameron June 14, 2013 at 12:21 pm - Reply

    Thanks, I never thought of that!

  11. Kristin of Be My Travel Muse June 14, 2013 at 1:33 am - Reply

    I’m the exact same way, I don’t plan a thing. The few times I have, it ended up being a flight I decided I didn’t want to take or a place I just wasn’t ready to go to yet.

  12. Stephen June 13, 2013 at 7:08 am - Reply

    I should definitely consider Romania for a digital nomad base in 2014. Thanks for the good idea.

    • Wandering Earl June 17, 2013 at 10:05 am - Reply

      Hey Stephen – I highly recommend it 🙂 If you have any questions about Romania that might help you decide, just send me an email of course and I’ll give you some more of my thoughts.

  13. Helen June 13, 2013 at 6:03 am - Reply

    Exactly how I like to travel too! Great post!

  14. Jonas June 13, 2013 at 4:43 am - Reply

    Thank you so much for all your help Earl, you have made me decide to travel away and never come back in the end of august :). The only question I have is whether I should go to Playa del Carmen or Mexico city as my first travel and hopefully stay there for a year or so. What would you recommend? I am looking for things there that can keep me there (such as work etc).

    Thank you so much for the answers 😉

    Regards Jonas

    • Wandering Earl June 17, 2013 at 10:06 am - Reply

      Hey Jonas – That’s a tough call as those two places offer completely different experiences. Maybe it would be best to choose one, travel there and test it out first. Maybe you will love it and want to stay for the year, maybe you won’t like it so much and then you can move on to the other option. Seeing both in person is probably the best way to decide. I love them both and I’m not sure how to choose one over the other!

  15. Megan June 13, 2013 at 12:44 am - Reply

    I like to travel in a similar way, Ryan! I find that since I basically want to go everywhere, its pretty easy to pick a place based off of traveller tips or “just because.” It’s all exciting and wonderful.

  16. Wil @ Where's Wil June 12, 2013 at 11:40 pm - Reply

    I travel plan-less as well. It’s a great feeling to just travel with the wind.

    The only issue I’ve run into is not being in a place where you can get a visa for the next place you want to be. (Though so far it’s just limited the time I can spend in the next destination rather then preventing my travels there)

    Such a freeing lifestyle.

    • Wandering Earl June 17, 2013 at 10:07 am - Reply

      Hey Wil – There are definitely a few obstacles to traveling this way, with the visas being one, but like you’ve figured out I’m sure, it’s not the end of the world and still worth the freedom of plan-less travel!

  17. Aaron June 12, 2013 at 4:47 pm - Reply

    Earl – I have a logistical question on your style of travel. How do you manage to travel affordable with this style of travel? It seems like you can get good deals close to departure for short distance flights, but that doesn’t tend to be the case for long distances. Pricing out flights from the U.S. to Europe you will often have to pay more for a one-way flight than the cost of a round trip ticket. Not to mention booking flights close to departure always seems to dramatically increase prices. Do you have a different strategy for long distance travel from travel within a single region?

    • Wandering Earl June 17, 2013 at 10:13 am - Reply

      Hey Aaron – It’s interesting because I never really find flying, even long-distance, to be that expensive these days. Of course, it helps if you are completely flexible, which I am most of the time. So if the route/dates I’m looking for are too expensive, I’ll simply choose another destination or another date and go from there until I find a reasonably priced fare. And yes, sometimes roundtrip tickets are cheaper and in those cases, I will sometimes buy a roundtrip ticket. I’ll try to estimate when I might be heading back to a certain place in the future and choose that as my return date. Sometimes I don’t use that portion of the ticket and other times, it somehow randomly works out and I am on that return flight.

      It’s the flexibility that matters though. If I want to fly to Europe and every destination seems to cost a lot to fly to, I might start looking at Asia or Central America instead until I find a ticket that is in my price range.

  18. Moeby Rush June 12, 2013 at 4:05 pm - Reply

    This is helpful, because I’ve been in South America 9 months and have spent about 6 months of that happily in Lima, Peru. I’ve been feeling anxious that I am missing out on the rest of the world by staying here.
    It is helpful to know that sometimes it’s good to just stick around somewhere if it’s working and also how you are using a base to operate from also. I am tenatively planning, until I have the ticket in hand and board the plane, plans could change, to go to Europe and wander for the next 4-9 months.
    thanks for the fun info

    • Wandering Earl June 17, 2013 at 10:09 am - Reply

      Hey Moeby – As long as you are happy with your travels and how long you spend in each place, that’s all that matters. It doesn’t matter if you stay in Peru for 10 years and never see anything else in South America! Everyone’s travels are different and again, if you are happy with your decisions, you’re doing it all perfectly 🙂

  19. Amelia June 12, 2013 at 3:37 pm - Reply

    You live a truly inspiring lifestyle. It must be wonderful to to unconstrained in such a way. I can’t wait to travel the world and hope one day, like you, to have a career that can fund and create this kind of life style. I just wish, I was less of a planner and more of a just do-er! Wouldn’t want over planning to hold me back!

  20. I’m a lot different in that I plan at least 6 months in advance where I’ll be heading, but that’s also because I do the long term immersion travel route, staying in countries for months at a time. So I like to plan things far out.

    Apartments, 100%, all the way. I still haven’t done house-sitting, although Cris and I are looking into that for the travels we have planned in 2014. Seems to work for a lot of people, so we are going to try it on for size. In which case, planning the trip in advance is a requirement because you somewhat need to go where the housing is as opposed to just picking up and going like you can with an apartment rental.

    As far as sticking around goes…I’m like you in that regard. Sometimes it’s only for the initial three months I get on my passport. Other times, if I like it enough, I stick around for longer…such as in Bulgaria for close to three years, and now Mexico for close to three years (hitting the mark in September).

    Great post, as always!

  21. Reka June 12, 2013 at 1:30 pm - Reply

    Is that Nagyszeben on the picture?

    • Wandering Earl June 17, 2013 at 10:14 am - Reply

      Hey Reka – I don’t know where Nagyszeben is (sounds like it would be in Hungary?) but the photo is Brasov, Romania 🙂

  22. Janet Wehrer June 12, 2013 at 1:29 pm - Reply

    Thank you for answering people’s questions on your post. I am enjoying reading your answers. I used to think I had to have everything planned but am doing less and less.
    I have done a couple of trips with a friend that is an extrovert. She will ask anyone
    anything. Local people are always happy to tell you about their favorite places. Going through Maryland, people had lots of opinions. You just have to listen to them all and figure out what works for you. Although, they persuaded us to try a beach with
    only one hotel. Thank goodness it was open. You have to watch out for information from the day trippers. I am always learning. Always.

  23. Terry Cameron June 12, 2013 at 12:56 pm - Reply

    Just wondering, in the spirit of not planning how much time to spend somewhere, how do you get around the fact that alot of countries won’t let you in unless you have a ticket out? Do you somehow convince the immigration officials that you truly are not going to overstay your welcome?!

    • Wandering Earl June 13, 2013 at 12:30 am - Reply

      Hey Terry – I’ve never been asked by any immigration officer in any country for a ticket out. What normally happens is that the airline staff (when I go to check in for my flight to a particular country) won’t let me on the plane unless I show proof of an onward ticket. So to get around this, these days, I usually buy a fully refundable one-way onward ticket. Once I land in the new country I simply hop online, cancel the ticket and get the refund.

  24. Ryan from Jets Like Taxis June 12, 2013 at 12:13 pm - Reply

    Great post, Earl! While we’re not as last-minute as you are, most of our destinations are completely random, based on a notion or a vague reason that could be as simple as ‘they have good beer’ or ‘we talked to someone there once’ or ‘we saw it on the map’.

    It’s certainly not for everyone, but we don’t have ‘bucket lists’ or ‘destination goals,’ and we like to go with the flow. We also understand that everywhere can have the potential to be great. Something new is something new; and for us, it’s always rewarding.

    As always, thanks for being the best at what you do!

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