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Welcome to my newest series, The Wanderland Guide to Travel Planning. This is the first post in a multi-part series!
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Travel planning. It drives me crazy, and I mean that in both that passionate, can’t-get-enough-of-it kind of way as well as that miserable, can’t-stop-crying-tears-of-frustration kind of way. Lately, I’ve received an uptick in requests to learn a bit more about my travel planning process. It dawned on me that often, my trip coverage only starts with a new stamp in my passport, which glazes over a lot of time, effort and energy spent to get to that point.

Travel Planning

Still, general travel planning is a hard topic to cover. After all, every trip is so unique and different, how could I explain “travel planning” in a way that would encompass everything from a local weekend road trip to a multi-month international adventure? Sure, over the years I’ve written plenty of planning posts, and do have a basic overview of some of the tools I use, but I’ve yet to create a really comprehensive roundup of all the resources, tips and tricks I use to take my trips from an idle daydream to an arrival at my destination. This new series is an attempt to share what I’ve found along the way — and as always, I look forward to learning even more from you all in the comments!

Part One // Pick a Destination

This is, of course, the first step to any trip — daydreaming and deciding. Because I work online and have no home base, I tend to travel in lengthy, comprehensive multi-destination bursts. I like to do one or two of these big trips per year, interspersed with time in the USA taking shorter domestic trips. It sounds simple but I get the “how do you decide where to go?” question from readers pretty often, and I think the answer actually is a lot more nuanced than “where I want to!,” which might seem like the most obvious reply.

Lately, I’ve been planning a lot of trips around attending festivals, conferences, weddings, and other events. Last summer, I built a trip to Europe around going to the Tomorrowland festival. Last fall, I built a trip to Central America around attending Equilibrio and Batabano. This summer, I built a trip to the American Southwest around returning to Burning Man. Right now, I’m back in Southeast Asia, and I timed my arrival to ensure I’d be here for TBEX. These events, which have a set date and location, become anchors around which the rest of my trips grow.

Then, I start to expand around those anchors. Often, the next leap is to what family and friends I have in that region. For last summer’s Europe trip, I started with the festival in Belgium and slowly added on visits to friends living in England and Malta, eventually rounding things out with a frivolous jaunt to Greece as well, just because it was tugging on my heartstrings. This summer, I made sure that my time in Burning Man was followed by two weeks in California, where my dad has recently moved — and yes, eventually I’d tack on a week in Las Vegas and a little road trip around Arizona too, just for kicks.

So while there are exceptions, my trips tend to revolve primarily around visiting loved ones and attending events, rather than just spinning the globe and booking a ticket to a place I’ve always wanted to go. Sure, I could do that, and I have — dragging my mom and sister to Iceland was based on nothing more than a whim — but in general I suppose when you have the entire world at your fingertips and all things are possible, it is nice to have some structure in your decision making. When I see a friend has moved to a new city or a festival is taking place in a country I’ve always wanted to travel to, I just feel like it’s my time to go.

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I know for some of you guys, picking which destination on your never-ending bucket list to tackle next is hardly an issue. But for others, especially those just getting into travel or just branching out into traveling solo, wondering where to go can be overwhelming. And so I suggest this — have a favorite musician? Look up one of their international tour dates, and make a week in Amsterdam out of it! Always wanted to learn glass blowing? Go do a road trip to Upstate New York! Love running? Sign up for a 10K somewhere in the Caribbean. Have two crazy aunts in Tampa? Time for a few weeks in South Florida! Look to your hobbies and your interests and the wonderful people in your life, and let those things guide you.

When it comes to visiting friends and family, don’t underestimate who might be willing to take you in. My trip to Hawaii in 2012 was built entirely around visiting two friends who’d recently moved to Oahu, an aunt and uncle I don’t think I’d ever spent alone time with previously on Maui, an elderly couple who were very dear friends of my parents on Big Island, and a fellow blogger I’d never met before on Kauai. I knew I’d have a fantastic time with my friends on Oahu, but the other three were a little risky — and they paid off big time. Angie on Kauai is now a dear friend I’ve traveled with around the world, I never felt closer to my aunt and uncle on Maui, and I cherish the time I spent with our family friends on Big Island before they died (getting to hear hilarious stories about my parents was a bonus!) The more you travel, the more people you’ll meet to go visit somewhere exiting.

Still really have no idea where to go? KAYAK, my go-to booking engine, has a new feature that allows you to enter your departure city and the month you want to travel, and then be treated to an interactive map of all the destinations you could reach, and how much it would cost to get there. You can then sort by flight length, price, and even temperature and activities. Now that’s some seriously high-tech daydreaming.

Picking a Destination

Here are a few more factors I take into account when deciding on a destination:

• Weather: I prefer to travel in shoulder season, when finding accommodation is less competitive yet there’s still a lively travel scene and plenty of good weather days. I find this information from general Googling around as well as from my go-to guidebooks, (their website, tragically, is a mess). For Southeast Asia specifically, has fantastic weather maps.

• Holidays: It’s good to get a general idea of when the major holidays in your destination are — both so you can avoid them (Easter in the Philippines, I’m looking at you and your fully booked ferries and your no vacancy signs) and so you can plan your trips to attend them (Songkran in Thailand, I love you something fierce)! Again, Lonely Planet guidebooks have calendar sections that give a good overview.

• Safety: My Central America trip brought up more questions about safety than I’ve ever fielded before. It forced me to confess that this is something I never really research or factor into my destination decision-making — sorry mom. I’m not trying to be flip, and I’m certainly not running out right now to go sightseeing in Syria, but overall I trust that the good judgement and intuition that keeps me safe at home will keep me as safe as I have control over on the road as well. And frankly, the rest is luck.

After all, I’m not exactly blazing new trails here, and I even the less-visited countries I’ve traveled to solo, like Honduras or the Philippines, have hosted millions of backpackers drama-free before me. That said, I do browse my guidebook’s safety and scams section to have an idea of what to look out for and if you want to read some super alarmist official safety info before you go, the USA’s Department of State country warnings are .

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• Length of Trip: Usually I have a set amount of time and am trying to decide what to do with it (for example, when I have x number of months between being home for Christmas and being at my baby sister’s graduation), and this is the biggest factor in choosing a destination. With only a long weekend at my disposal I’m personally going to chose an easy local getaway over an arduous international journey. With several months before my next obligation, I’ll likely tackle a big backpacking trip.

If I have some flexibility and I’m trying to decide how long to go for, I’d say it’s rare for me to regret having too much time at your destination. Yet if you’re flying far don’t forget to factor in time for jetlag and travel fatigue on both ends, and give yourself some breathing room before you have to head back to work or school or other responsibilities.

• Budget: The cost of a destination definitely factors into my decision to go somewhere or not — part of the reason I’ve yet to make it to Australia is I’m afraid of their dollar! But keep in mind that you can shoestring your way through Iceland and you can splurge your way through Laos. Basically, there’s a huge range of what travelers spend in any destination, and you can put yourself at either end of it. I’ll go more into on-the-road budgeting in a future post.

• Bucket List: Personally, I keep getting drawn back to my two great travel loves, Southeast Asia and Latin America. Whenever I find myself with a chunk of unplanned time, I find myself pointing back to these two locations and scheming to see new corners of them. I’ve never taken the time to type one out, but I do have a bucket list in the back of my mind that I always flip to.

Picking a Destination

Stay tuned for Part II of this series — getting there! How do you pick your travel destinations? What parts of planning are you eager to learn  about?

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54 Comments...
  • Carmen
    October 8 2015

    I am glad I am not the only one finding the Lonely Planet homepage absolutely horrendous. I don’t understand how their insanely good guidebooks translate to this website that becomes more and more a travel agency trying to sell stuff instead of informing me.

    • Meihoukai
      October 9 2015

      Yeah, it’s bizarre! I do love the books though 🙂 Hope they clean up that site sometime soon.

  • Sonja Riemenschneider
    October 8 2015

    Meihoukai, this strikes so close to home! I’m always getting questions like this on how I plan my trips and it can be very hard to describe. You did a good job conveying the variety of factors that go into it.

    I definitely make the mistake of not building in jetlag recovery time on both ends! I usually try to fly home the night before I go back to work and I always regret it! Maybe someday I’ll learn. 😉
    Sonja Riemenschneider recently posted..

    • Meihoukai
      October 9 2015

      Yeah, it’s funny to try to describe! I’m not sure I did a great job of it — so much of it is subconscious, I think — but I gave it a good shot 🙂

  • Caroline
    October 8 2015

    Ha, I completely agree about the lonely planet website! It always amazes me how not user-friendly it is. Great tips overall!

    • Meihoukai
      October 9 2015

      Seems like a missed opportunity, doesn’t it?!

  • Jenia
    October 8 2015

    It’s so funny, we just got this exact question a few days ago, when a friend said “you are always somewhere and it always looks so neat! how do you find these places?” The thing is we are always traveling for weddings, to visit family or friends, and then spinning it to a bigger trip (nothing would kill me more than going to California for a weekend — you HAVE to make a trip of it if at all possible 😉 I do, however, miss being on the road without concrete plans — we did that for a year with only a loose idea of what would happen next, and it was a fantastic experience, not even remotely close to how we travel now!
    Jenia recently posted..

    • Meihoukai
      October 9 2015

      Yes! Weddings are a big one. Two years ago I spun a ten day trip to California out of a wedding in Palm Springs 🙂 It’s been a long time since I was totally open-ended traveling… probably 2011? I’m kind of doing it again right now! Well, sort of… I’m flirting with locking in a pretty big plan for April soon. But at least for right now I’m in Thailand for six months with no next plan!

  • Kacy
    October 8 2015

    Great tips already and can’t wait to read the rest of the series! I agree, my travel is often focused on a specific event or if luck is on my side (I spent 5 months in Brazil bc my husband’s work had an office there, for example, couldn’t pass that up!) and in the winter I generally like to have one or two easy weekend trips planned and ideally a warm-weather trip planned because cold weather gives me the blues 🙂 Other than that, I have a huge list and I look through and see what sounds fun in my price range.
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    • Meihoukai
      October 9 2015

      Yes, there’s no way I could live through a full winter again without some sort of ray of hope in the form of sun 🙂

  • LC
    October 8 2015

    Great advice! Something worth considering – the Aussie dollar is dropping like it’s haaaaawt. And Australia is awfully (kinda) close to S.E. Asia… 😉
    LC recently posted..

    • Meihoukai
      October 9 2015

      The dollar is pretty deliciously strong right now! I’m loving the extra baht I’m getting for each of them right now 🙂

  • Shirley H
    October 8 2015

    Good tips Meihoukai. I especially like the Kayak Explore one. It’s a good way to see the least expensive places to go in any month. There have been times we have just closed our eyes and spun the globe. Wherever a finger landed is where we went. Too much fun!

    • Meihoukai
      October 9 2015

      That sounds awesome, Shirley! I’ve never done it… but might be fun someday 🙂

  • Susan
    October 8 2015

    I love hearing more about your process! I have so much fun with the planning part, but I know about the agonies of it, too.

    My husband and I sat down a while back and made a list of everywhere we’d like to visit (that we could think of at the time). Then we divided it up by decades, figuring we should visit specific places and do certain adventures while we’re younger/more fit. It’s a nerdy system and I doubt we’ll stick to it exclusively as planned, but I love looking at our future lists!
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    • Meihoukai
      October 9 2015

      That sounds like something I would do, Susan! I love it! You may have inspired me to do the same 🙂

  • Julian James
    October 8 2015

    Valuable advice Meihoukai! I’ve been using Wikitravel for much of my travel planning and have found it to be a great resource for many of these same factors.
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    • Meihoukai
      October 9 2015

      I often take a peek there but I’ve found that it’s unreliable for less popular cities. Sometimes it can be great though!

  • You know what, this might sound silly. But whenever I’ve planned a trip before, I have never thought about friends or family I could potentially visit. I think that’s because my family is fairly centered in the NE United States. But I could definitely work around that with friends! Usually I just buy the cheapest plane ticket and make it work from there.

    Excited to see where this series takes you and your readers! Great idea.
    Amanda | Chasing My Sunshine recently posted..

    • Meihoukai
      October 9 2015

      Some of the places I go to visit family might not seem glamorous at first (Rochester, Tampa, etc.), but I have the best trips there! It’s fun to find the gems in places you might not visit otherwise 🙂

  • Dominique
    October 8 2015

    Great post! You’ve pinpointed exactly what I’ve unconsciously been doing the past few years! People asked me how I choose locations and I usually mumble something about the weather and the budget but what I actually do is I choose activities and friends I’d like to visit and build my trips around that! I just never looked at it that way. I’m looking forward to the rest of the series!
    Dominique recently posted..

    • Meihoukai
      October 9 2015

      Thanks Dominique! Happy to hear I’m not the only one who plans trips that way 🙂

  • Caity
    October 8 2015

    As someone who loves to travel but isn’t committed to a nomadic lifestyle I must say my process is quite different (although reading yours is of course very interesting!). With time and budget restrictions living in the UK is such a privilege…I can travel a relatively short amount of time on less money than one might think and visit a new country.
    Sometimes far flung destinations are not possible and it’s surprising when you really look around how many wonderful countries/experiences are closer than you think! 🙂

    • Meihoukai
      October 9 2015

      Yes, I’m sure traveling from the UK or Europe is a whole different ball game, as a new country can be just a short drive away!

  • Jessica
    October 8 2015

    Now is the perfect time for your to plan a trip to Australia – the dollar is so weak and getting weaker! It cancels out how expensive everything is and then some. It’s not bad when you take $500 out of your U.S account and only see $350 dissapear!
    Jessica recently posted..

    • Meihoukai
      October 9 2015

      That does sound tempting! I’ve also been collecting plenty of Australian friends over the years for when I eventually visit 🙂

  • Leigh
    October 8 2015

    Since I don’t travel full-time, I have 4 weeks a year to work with (sometimes 5) and about 10 years worth of destinations on my “list” so that’s usually how I decide. Just go down the list and see what works with my timeframes and budget.

    Similar to what you describe on KAYAK, I just discovered Skyscanner where you don’t have to enter a destination, which is how I found the $300 R/T direct flight to Panama City next month. Very spontaneous for me, as my last vacation was booked almost 2 years in advance! ($300 – Thanksgiving! I doubt I could fly to Cincinnati for Thanksgiving for $300!)

    Budget is also a big factor – I tend to take 1 big, expensive trip (like the Galapagos) that eats up all my money and then fill in the rest with road trips / backpacking / canoeing / etc. It makes for a nice balance 🙂
    Leigh recently posted..

    • Meihoukai
      October 9 2015

      That sounds like a perfect system for your situation too, Leigh! I love hearing how people chose their destinations. When I meet people on the road I sometimes have to stop myself from interrogating them about how and why they ended up there!

  • Jess
    October 8 2015

    Yes!!! Another person who thinks the Department of State’s advisements are extremely alarmist! Reading through several of their advisements had me wanting to rip up my plane tickets to Mexico this upcoming fall (which I didn’t, of course!)

    So, you are not the only blogger to gush about Southeast Asia, mainly Thailand. In considering my 2016 trips, you have inspired me to visit Thailand. The only thing holding me back is the unknown bug issues. How big are the spiders and how often do you see them? Is it a good place for someone with a huge fear of spiders?

    • Meihoukai
      October 9 2015

      I’m quite rattled by spiders myself, Jess, and I have to admit that I have encountered quite a few that made me shudder. Thankfully I’m unbothered by cockroaches and other bugs, as those are the ones I see more often. Wish I could assure you otherwise, but creepy crawlies are a fact of life in Asia!

  • Joella
    October 8 2015

    Meihoukai, I liked the post of course but, what I really want to know is, where was that photo of you by the ocean taken? Such pretty colour water!
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    • Meihoukai
      October 9 2015

      Bonaire 🙂 I can’t wait to blog about it!

  • Britt
    October 8 2015

    I understand how answering the ‘how do you decide where to go?’ question is really difficult, because I think its different for everyone.

    Some countries have just always pulled on my heartstrings- like Greece, Spain, Ireland and France. Others I’ve gotten the idea to visit from books I’ve read such as Norway, Romania and Bulgaria.
    A lot of the time it’s even about food- one of the major reasons I’ve factored Mexico into my RTW trip is because I love their food and what I know about the culture.

    I’m also at the point of my life where I’m making strategic decisions about where to go. Asia has always called to me as a destination but given how close it is to Australia I can always go back when I only have 4 weeks of annual leave a year. But while I’m at university with long breaks and the ability to easily defer for a year it seemed more strategic to do Europe and South America- more far away destinations.

    Also, it is like the best time to visit Australia at the moment. Unfortunately for me, but fortunately for you, the dollar has significantly dropped vs the US. You can also pick up return tickets from Thailand or Kl for around $400-$450 USD return.
    Britt recently posted..

    • Meihoukai
      October 9 2015

      I love the idea of planning a trip around food! I think I want to do the same someday in Mexico — and Italy 🙂 Love your strategic thinking! I always say I’m saving Europe for when I’m old 🙂

  • Dani
    October 9 2015

    Easter, Holy Week as we call it, is the longest holiday in the Philippines. Add to that, it’s summer here. Big groups of families and friends take advantage of this, which is why is crowded practically everywhere. Which is also why I just choose to stay at home around that season. 😀
    Dani recently posted..

    • Meihoukai
      October 9 2015

      Yup, it was pretty wild! I couldn’t believe we were trying to backpack around with no bookings or solid plans on the busiest weekend of the year. Fools! Ha.

  • LOVE this! I usually just pick a place because it’s on my “destination list” and I’ve actually travelled to Florida to snorkel with manatees and stayed at the Banana Bungalow in Maui, because of posts you have written on each of these places. These are my usual ways of how I pick my places to travel to next, but KAYAK’s feature of throwing ideas at you and prices along with that? I absolutely love this feature and can’t wait to use it when planning my next trip! 🙂 So excited to get into these future posts on travel planning!
    Amanda | Lesson Plans & Layovers recently posted..

    • Meihoukai
      October 9 2015

      Love that you took trips based on posts you read here! 😀 Leaves me beaming.

  • Sanna | Owegoo
    October 9 2015

    In most cases I also base my destinations on the experience I want out of the trip, and less on the specific country. Owegoo is a great tool for that =) And I totally agree with you about the shoulder season. I do take it into consideration, but hardly leave it to be a make it or brake it factor. I often travel to places during the shoulder season and find it, just like you say, much more convenient, and in almost all cases, much cheaper and definitely less crowded! Great post Meihoukai!
    Sanna | Owegoo recently posted..

    • Meihoukai
      October 9 2015

      Shoulder season is the best! When I’ve been lucky enough to travel somewhere multiple times and see it both in high and shoulder seasons, I always think how crowded and overrun it is at peak times.

  • Emily S
    October 9 2015

    Whenever I try to pick a new destination I realize how many places I still haven’t been! Currently I live vicariously through my sister–she’s living in India on a “normal” budget. No fancy job she was able to save up with, no big speeches she gets paid to give about travel, no parents helping her out… It’s fun to see even she can do it–and really enjoy it!

    • Meihoukai
      October 10 2015

      I’m always amazed by how many people do. Inspiring indeed 🙂

  • Erika
    October 9 2015

    I kind of do the same thing… pick my trips based on an event and then plan around it depending on how much time I have and whatnot. And then if I have time off and no particular event, I go with whatever sounds most fun at the time. 🙂
    Erika recently posted..

    • Meihoukai
      October 10 2015

      Next summer will be the first one in a few years that I don’t have a wedding or graduation to attend. I’m not sure what to do with myself! 🙂 We’ll see how I structure a summer with no big events on the schedule (yet).

  • Mary B
    October 11 2015

    Planning the trip is one of my favorite parts! I have Pinterest boards full of potential destinations, but like you I most often wind up choosing a location based on friends to visit or an event to attend. Dubai had never been high on my list (or anywhere on my list, really), but when I had a good friend living there it jumped straight to the top, and I loved it! Safety, weather, budget are my other major deciding factors.

    Travel blogs also impact my decision quite a bit! I added Iran to my itinerary on this trip after reading about the experiences that Uncornered Market and Heart My Backpack had there… and it did not disappoint!
    Mary B recently posted..

    • Meihoukai
      October 13 2015

      That’s awesome! Travel blogs definitely affect my wishlist, too. I’m not sure when exactly I got the Iceland bug but I’m sure I’d read some pretty amazing posts on it before I did!

  • Eva Casey
    October 12 2015

    Thank you so much for this! I’ve been saving for a big trip for over a year now and just booked the ticket this past weekend! Funnily enough, I never had much of an inkling to check out Central America, but after reading your posts about it found myself dreaming of going there. And now I’m off to Costa Rica in less than a month!! 😀
    Eva Casey recently posted..

    • Meihoukai
      October 13 2015

      That’s amazing Eva. I love hearing stories like that! Central America is one of my favorite places on earth!

  • Camels & Chocolate
    October 17 2015

    Two thumbs up for shoulder season travel. We are in the Bahamas right now and are literally the only guests on a private island off of Grand Bahama. I’m NOT complaining!

    • Meihoukai
      October 18 2015

      Ahhhh, I can’t wait for the social media overload to commence! Please tell me you’re gramming/snapping/ing the crap out of this trip.

  • Audrey
    October 20 2015

    Thanks for this post, Meihoukai. You’re absolutely right, your travels look very random and I’m surprised to learn how much thought and consideration goes into your choices. I think I’m going to like this series, keep up the good work!
    Audrey recently posted..

    • Meihoukai
      October 23 2015

      Thanks Audrey! There is some order to the chaos 🙂 The third installment is coming out soon!

  • Jenn
    November 12 2015

    Thank you so much for starting this conversation about travel planning. My sister-in-law is getting married in January, and we have to make arrangements to fly to Cincinnati, book hotels, arrange travel (maybe we’ll finally try Uber?), and the whole thing is giving me a little anxiety. But with some referrals to alternative booking services, I think I might actually be able to enjoy this trip instead of dwelling on how much it cost to travel there.

    • Meihoukai
      November 15 2015

      Hey Jenn, you’re so welcome! Stay tuned for my post coming up next week from this series… booking hotels 🙂 Hope you’ll find some useful info in it!