My OCD Approach to Travel Planning

Call me crazy, but there is no planning activity more joyous than planning for an adventure. Don’t get me wrong, I love a good party and planning my wedding was okay, but nothing gets the hairs on the back of your neck tingling like searching through travel guides, blogs and Pinterest. A lot of folks that I know approach travel planning with much more ease than I do. They pick a destination and simply go, discovering their locale upon arrival.

Already planning for German Christmas markets in 2017!

Already planning for German Christmas markets in 2017!

The thing is, with a limited amount of vacation, I like to maximize my opportunities to see, do and eat as much as possible. If I’m going from Point A to Point B, I like to know the fastest way to get there (or the slowest and most picturesque) in order to either use my time efficiently or to be part of a magical experience.

Here’s how this OCD gal plans her travels:

Start With a Little Inspiration

Photos are the way to my travel inspiration soul. As such, Pinterest fits my needs perfectly. It’s through Pinterest that I discovered Yi Peng, the Thai festival in October/November where they release thousands of lanterns into the sky at once. Magic. That’s what those photos were. And you know what? I planned our entire adventure through Southeast Asia around being in Chiang Mai for that event. A little inspiration goes a long way.

Go onto Pinterest and plug in your country/city/activity of choice, and I have no doubts that you’ll find some photos to fuel your travel planning.

Pick the Right Dates for You

If you have a limited number of vacation days, perhaps your best option is to plan your trip around bank holiday weekends, giving you a bonus travel day. The downside of that is that holiday weekends are typically pricier on flights and hotels.

Are you going for a specific event, festival or activity that is date specific? Again, your price tag might go up.

things to do in Victoria

Travel to Victoria in the off season didn’t affect how much we loved it.

Are you willing to travel in the off season where you’ll encounter fewer tourists, possibly less desirable weather, but be able to stretch your budget further?

Whatever option you choose will be the right one, provided it fits YOUR needs. Picking the dates and booking your flight can be the hardest part of trip planning, as you’re often outlaying the biggest dollars in one fell swoop. Just make sure you think through your dates carefully, as there is nothing more soul-destroying than having to pay the change fee, particularly if you’re traveling with more than one person.

Find a Home Away From Home

Whether you’re staying in one location or hopping from city to city, your next biggest expense and planning hurdle is to find accommodation. My new favourite thing in the world is AirBnB. I’m almost as excited to stay in this country cottage on the Isle of Arran in 2016 as I am for visiting the island itself. Knowing that it will rain – ahem, Scotland – we picked somewhere warm, cozy and with a conservatory that’s perfect for snuggling up with a good book as the rain picks away at the glass.



In my hostel days, Hostelworld was my best friend in planning. Budget travellers are great at leaving reviews, be they good or bad, so you should have a good sense of what you’re walking into. I find hostel reviews to be pretty consistent, as well, given that most hostel travellers have the same expectations of what it means to be a decent hostel.

God love Expedia, but I’ve had much less luck finding good hotels through their website. Perhaps it’s just the overabundance, but we’ve stayed at some hell holes, which by all other accounts looked gorgeous and had great reviews.

No matter whether you’re on a budget or cashing in your travel points for free accommodation (we did this in Asia for the occasional treat) , repeat the mantra: location, location, location. There is ZERO point in finding a bargain hotel on the outskirts of town if you’ll pay the difference in time and money getting to and from the city centre every day. I’ve learned this the hard way… Google map the locations you’re visiting, then find some central accommodation to help you maximize your time. A little neighbourhood research won’t go awry either.

Begin Your Budget Planning

What’s this all going to cost you? When I did my round the world trip in 2005, I had… a rough idea of the cost. I also had a healthy bank balance at home to make up the difference. Did I overspend? Um… yes. Dramatically. Frighteningly. Since then, I’ve been much more attuned to my budget both before and during travels to decrease stress when I get back home and open that Visa bill.

This is where Excel becomes my best friend. Sigh. I used to hate Excel until I realized how this beautiful tool can keep ALL my information in one easy place.

travel planning

When I start my travel planning I keep a running total of costs, with a column broken down by category. I insert my flight estimates, travel insurance, pet care while I’m away, transportation to and from the airport, etc. Those are the ‘knowns’ before I go. If you’ve booked your accommodation or a car rental, same goes.

Once I know the kinds of places that I want to visit (museums, activities, etc.), I add them into the spreadsheet with their per person cost. After that, it’s as simple as estimating your per diem for food, souvenirs and local transportation. What kind of foodie budget are you on? Will you be hitting up the supermarkets, going the fine dining route or somewhere in the middle? Dig a little into online menus and you’re on your way.

If you’re going on an extended trip (a few weeks to a month), buy a tiny notebook and keep a running tally of what you’re spending. This method kept David and I on track throughout our three month adventures in Asia, and we came in UNDER budget with more experiences under our belt than I can count.

The Fun Stuff

Budgets, flights, accommodation… you guys are probably snoozing, so I left the best for last. What do you want to do, eat, see, etc? I adore digging online for those unique experiences. Google is your friend. Simply add “off the beaten path”, “unique” or “unusual” to your destination search and you’d be amazed at some of the gems you’ll find that might not be in your Lonely Planet guidebook. This is how I came to find many of my favourite travel bloggers. YouTube is another great resource for the visually inclined.

travel planning

Thanks to my crazy research, that’s how I found the opportunity for David and I to ride motorbikes in Laos. David’s an avid motorcyclist, and I got the 101 lesson, enough to get me on the road. It goes down as one of our most memorable experiences in Southeast Asia. Thanks Uncle Tom!

Finally, you can always ask friends, family or total strangers for advice via the joys of social media. Getting advice from locals is always great, so make sure you ask friends to ask friends. Six degrees of separation, anyone?

Okay… I’m starting to realize I’m a bit of a travel planning freak, but at least it brings me a LOT of joy. How do you plan your travels? 

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