Travel Tips & Tricks

My Travel Planning Process: Inspiration, Research, & Realism

November 28, 2018

I don’t brag about many things, but one thing I will consistently toot my own horn about is my travel planning process, and more importantly the outcome—I have a knack for planning EPIC TRIPS.

And one of the most important things about “epic” is that it all depends on what it means to YOU. Both a weekend jaunt to Chicago and a sailing trip in Sweden can be epic, if you do it right!

This is part of a series on how to plan epic trips. I’ve linked to the others at the bottom of this post, and you can also download my free e-book for dozens more trip planning tips on flights, housing, itinerary, and more!

What this post covers:

Getting inspired—how to choose your destination
A detailed process for trip research and organization
How to nail down your trip details

My travel planning process in a nutshell: Inspiration > Deep Dive > Reality

Over the years I’ve found a trip planning process that really works well for me. It’s fairly unstructured, so I can easily knock out a simple weekend getaway in the States, or use it to plan an intense two-week New Zealand road trip.

Like many things in life, I start fairly broad just to see what’s out there, and then I slowly filter things out until I have a solid, workable, and epic trip in front of me.

We’re going to dive into the overall travel planning process that guides me below. Then you can do a deep-dive into planning some of the individual elements with these posts!

Not sure where to start?? Key Questions To Guide Your Planning

How to Find (& Choose) the Right Flight For You

How to Pick the Perfect Hotel or Rental Every Single Time

How to Create Epic Itineraries…Whether Weekend Getaway or Bucket List Trip

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Step 1: Get inspired!

This part of the process is hardest for me to give advice on, because only you know why you’re taking a trip and what will make you happiest. Do you already know where you want to go? Well then, you’re set…move on to the next section 🙂

If not, or even if you just have a general idea, Pinterest is one of my biggest tools at the inspiration stage, and here are some of the steps that I then take.

If you know you want to go to the beach but aren’t sure where, start by Googling “best beaches to visit in [month]” to start getting some ideas.
Then search those on Pinterest to see what photos catch your fancy.
Here’s one of my absolute favorite tips: If you know you want to go *somewhere* and have timing but not a destination in mind, I’d recommend going to Google Flights, entering your dates, and then using the map to see what fares cost to different destinations—it even lets you enter something as broad as “Europe” or “Caribbean” to see what’s out there. This is how I’ve booked my last few trips, from Iceland to Colombia…just entered dates and then dragged around on the map.

While it’s not time to get *real* yet, I do recommend a slight reality check at this point…

While you’re not booking anything right this second (unless you find a KILLER flight deal, in which case lock that crap down!), it’s important to check the weather and flights at this stage, and have a sense of what housing would cost, too.

I’ve gotten down the path of picking a destination, and then realized that flights at that time of year are obscenely expensive, or that I’ve inadvertently picked the rainy season for Costa Rica.

Do a bit of Googling and scan some flights for placeholder dates—examples or estimates of what you MIGHT be looking at (make sure to consider day of the week too!)—to make sure that you’re on the right track before you head into real research.

Step 2: Research deep dive

This part is all about gathering as much information as you can get your hands on, then figuring out how to organize it. Save a brand-new Word doc or Google doc with your trip destination as the name, and start copying and pasting all the info you find into it.

Think of this stage of the travel planning process as one giant data dump. It’s messy right now, and that’s okay.

How I use Pinterest (and Google) at this stage

Pinterest is still a huge part of my process at this stage. I create a new board just for the trip, and then go through and do several searches. For my girls’ trip to Portland and the Willamette Valley, for instance, I searched things like “Portland itinerary”, “Willamette Valley wineries”, “Oregon hiking trails”, and many more variations, then saved all the pins that appealed to me to my new board.

If you’re mostly staying in cities, don’t forget to look for popular day trips from that city (search Pinterest & Google “day trips from [city]”). For instance, you’d be crazy to visit Lisbon and not see the palaces of Sintra, or visit Munich and not also visit Neuschwanstein Castle.

I then visited every link in the Pinterest board, copying and pasting any helpful advice from these articles into my ever-growing research document. If the website was extremely helpful, I copied the link as well, to reference later.

The critical role of TripAdvisor

I also start combing through the TripAdvisor forums for the destination to see what questions people are asking, who the most knowledgeable contributors are, and even asking a few initial questions of my own.

Once you have an idea of what landmarks you might want to visit, go to the TripAdvisor pages for each of them and read the reviews in-depth to see what tips you can glean (whether it’s under construction, when the lines are shortest—TA has all kinds of tidbits if you’re patient enough to sift through).

Again, copy and paste everything important into your Word doc.

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Starting to organize the chaos

Once you have quite a bit of information in the Word doc (which can easily be 20 pages long), go through and start to group everything by theme. If you’re visiting multiple countries or cities, start there and then sub-divide by site, neighborhood, or order you’ll visit in.

I almost always have a “basic important info” section at the top (language, customs, currency, sunrise and sunset times, weather, etc.), followed by “transportation” (i.e. ways to get around, train schedules, how to get to and from the airport, common taxi scams), and I always have “housing” and “food/drink” sections at the end of the document.

This document is absolutely fundamental to my travel planning process!

Step 3: Time to get real

Now that you know all 1,723 places you want to go on your 5-day trip, it’s time to talk reality 🙂 Reality = how many days, how much travel time to/from/between, and how much money you have to spend. Now you figure out what you feasibly can accomplish on this particular trip.

I save a new version of my Word doc and then start to edit my research down, cutting out duplication, and then start to highlight the things that are absolute musts, what are “nice to haves”, etc.
Next I choose the most important and just start going down the list, seeing what I can realistically fit into an itinerary.
If they’re not in the same city, look at travel times and schedules between them, to see how much time you’ll lose in transit and what routes and order of visiting would make sense.
The TripAdvisor boards are absolute gold here (mostly). Once I have a list of what I really want to do, I’ll put a post up on the destination’s board providing a little background on myself, my travel companions and likes/dislikes, then the sites I’d like to visit and time I have (and that I hate museums). I usually also caveat that my travel style is a bit more fast-paced than many people like, so fitting in a bit “too much” isn’t stressful for me.
The TA forum folks will provide invaluable recommendations on order of visiting, when to avoid certain areas, or sometimes even if my wish list just isn’t realistic. Take their advice with a grain of salt (when it comes to your preferences), but take it nonetheless.

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What comes next?

There are three key areas you have to figure out—transportation (flights, trains, car, or something else), housing, and itinerary (along with activities).

The biggest challenge is that the order in which you figure these out will vary by trip. Sometimes you’ll nab a great flight and then build your itinerary from there, filling in housing as you go. Other times, you build your ideal itinerary and then book flights, rental cars, and housing based on that.

Hopefully I’ve shown that you don’t need fancy tools or programs to plan an amazing trip. Between Pinterest, TripAdvisor, and simple Word and Excel documents, you already have all the tools you need to develop, research, and fully plan a detailed trip itinerary! I use it every time I plan a trip.

I’d love to hear from you with any questions on my trip planning process, and also if you have tips that always work for you…hit me up in the comments!

Other resources for epic trip planning:

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