The Wanderland Guide to Travel Planning: Picking a Destination

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.

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.

Photo by Zoe Norvell

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 Explore 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.

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, Lonely Planet (their website, tragically, is a mess). For Southeast Asia specifically, Travelfish 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 here.

Photo by Kristin Luna

• 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.

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?