How To Start Planning A Trip in 2019

Watching people be awesome on kiteboards isn’t an attraction in a guidebook.

Pick a place, any place. How would you go about planning a trip there? What if no one you know has been there before? How much should it cost? What should you do? Where should you stay? How long should you go for? In what season?

These are incredibly intimidating questions to answer and it doesn’t matter if the destination is Napa Valley or Nepal. If you’ve never done it before, it’s uncharted territory.

I remember when we decided to go to Malaysia, we felt in over our heads: none of our friends had been, we decided to go there because some random dive guide told us to, and the breadth of places to visit and things to see was significant. The only thing we knew we were going to do was dive for 8 days…but that left some additional days. Days we didn’t quite know how we were going to fill. And the old options of figuring this out…they were hopelessly outdated AND hopelessly not for us.

Once upon a time, there were guidebooks. I know because I bought them. For our 1999 trip through Europe, I bought an astonishing number of them, and I learned an important lesson: guidebooks are written for the plurality. Yes, there are guidebooks for luxury travelers and guidebooks for budget travelers, but the guidebook is hoping to reach the greatest number of people with its content…and therein lies the problem. If the guide’s research tells it that a statistically significant portion of its audience will want to know where to get pizza in Morocco, it’s going list a pizza place in its dining section. Space constraints of the guidebook suggest you’ll get a small handful of lodging options where the budget option is a hostel, the mid-range option is a hotel by the train station, and the upscale option is either wildly more than you’re willing to spend or not nearly upscale enough for your tastes. I’m willing to say that the internet killed the guidebook.

But the internet isn’t, necessarily, much better. Scroll through tripadvisor reviews and you’ll find it nearly impossible to find what you, personally, are looking for. Don’t believe me? The 5th most popular attraction for Penang, Malaysia is…a teddy bear museum. More galling, though, is that in Penang, ONE OF THE GREATEST FOOD TOWNS ON EARTH, the second most popular restaurant serves French food and the third most popular restaurant is a fucking Irish bar.

Yeah, TripAdvisor, I totally wish I were eating bangers and mash instead.

And this is why travel planning takes time…lots of time if you are a type-A weirdo for whom a disappointing vacation ranks up there with a tree falling through your roof. I don’t plan my vacations down to the last hour – I actually like when we can “go where the day takes us,” but I do like having an outline and some things to slot in that have been researched, vetted, and approved. This way, if the day doesn’t take us anywhere in particular, we’re not left with nothing to do. I like knowing where I’m going to sleep simply because not having a place to sleep meaning I’m using “vacation time” to work on logistics (and I can use “office time” for that). I like knowing that if I don’t pass a place that smells so good, I have to stop and immediately consume whatever I’m smelling, that I have a list of places I can eat – places I’m looking forward to eating. Planning, for me, facilitates spontaneity.

So here’s the first step in how I plan a trip. And it’s good timing too since I am starting to actively plan one to a place we’ve never been before: Sri Lanka. Sri Lanka is pretty big, pretty weather-dependent (hi, monsoons), and pretty awesome looking. I want to do it justice.

How much time do I need? What should I not miss? What am I getting myself into?

I originally tried to shoehorn this trip into 10 days. That was stupid. I’m now looking at 2 weeks. And how did I determine that? I googled: “sri lanka itinerary,” and read results until one resonated with me. I realize that is entirely subjective, but in order to find the things you want, you have to wade through a lot of people you don’t want. From Malaysia on, I’ve found that travel blogs are my best friends…provided that the travel blogger’s ethos accords with my own. This is incredibly time consuming and incredibly worth it. Because I found these people, and now I have a much better jumping-off point for this trip. How do I know I can trust them?

More outdoorsing, less shopping is where we fall on the spectrum

This introduction to the itinerary was certainly heading in the right direction: “To be honest, Colombo isn’t really worth spending a lot of time in…” which led me to think that these people weren’t going to suggest I visit a shopping mall or eat wood-fired pizza. The itinerary I found (which will form the basis of our own) doesn’t seem, on the surface, to differ much from what you’d find in a guidebook…but it kind of does. Aside from the tea museum, there’s not much that feels hokey. There’s a strong preference given to things that can be done outdoors (our preference as well). Their budget for lodging dovetails nicely with our own (nice, clean, comfortable, but now fancypants). The only thing that’s missing is where I should go for the best chow…but that will be a discovery for another blog (as I said, I’ve only just begun this planning).

What reading the Finding the Universe post has done is lower the intimidation factor significantly. I don’t know those people, but they seem to know me – or the kind of traveler I am – and now I have a jumping off point. From here, I can get really excited about transit, diving, and eating all the things! I’m more excited now than I was when Sri Lanka was merely one of the places on my top 20 list, so I guess I’m arguing that finding someone on the internet who has gone where you want to go and who talks about it the way you’d want to talk about it, is the essential first step to planning any trip.

And if touring the world and eating wood-fired pizza is your jam, I assure you there’s a blog for that too!



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