Planning for a Trip the Obsessive Way

There are two kinds of travelers: those that flow freely with the ebb and tide of travel, making plans as they go and hoping that everything rolls out for the best. Then there are those that like to have all their ducks in a row, all their roads mapped out, and all their rentals and reservations confirmed beforehand. Usually, if you are of style A, you shouldn't be traveling with someone who leans towards style B, lest frustrated and murderous thoughts lead you to making some poor choices.

Fjaðrárgljúfur Canyon, Iceland. Image courtesy:

As much as I'd like to be someone who just flits along merrily, assuming the universe will roll out a red carpet for me as I go, I'm not. I need to know that when I land at the airport, I know how to find my hotel. I need to know my hotel is expecting me, and that I won't be sleeping on the streets that night. I need to know that when I want to drive through the beautiful countryside, I have a car (or if necessary, a 4x4) waiting with a full tank of fuel and a spare tire in the trunk. With these things prepared and ready, I can then enjoy my time in a foreign country, seeing the giant list of things I`ve researched in advance.

Yup, I'm a travel nerd. An obsessive, type-A-personality, PowerPoint-havin', reservation-callin' travel nerd. And that works for me.

My husband is a bit more free-spirited. He doesn't mind bouncing from hotel lobby to hotel lobby until he finds a free room, even if that free room is a 10-bed dormitory with one shared bathroom. He doesn't like having an itinerary of things to see and do - he'd rather float through the city or countryside and discover things for himself.

Shared dorms are not my style - sorry! Image courtesy:

Now I'm not saying that his style is wrong. But my argument is: a) EW! on the 10-bed dormitory style hostel with one nasty shared bathroom... that is all I have to say about that. And b) when you don't research the country you are about to visit, you will inevitably miss out on some of the hidden gems. Sure, signs and pamphlets at your hotel or the airport will tell you about the major attractions, but what about the little places that, unless you speak the nation's language fluently and can chat openly with locals, you will no doubt miss out on? I prefer to have a plan of attack, thank you very much.

Iceland, here I come! Image courtesy:

In July, we are headed to Iceland. I have been researching Iceland since November when we began tossing ideas back and forth about places we might want to visit in the summer. Six months have gone by, with me doing the following to prepare:

1. Created a Pinterest board with Iceland ideas - big attractions, tips from locals, amazing photographs of waterfalls and geysers, and places I'd like to see and things I'd like to do.

My obsess-much Pinterest page on Iceland

2. Dug deeper into some of those Pinterest photographs and looked up websites on locations, driving distances, costs, hours of operation, and reviews from past travelers and locals alike.

3. Charted a pretend trip itinerary and slapped my must-see destinations in logical calendar order to ensure we'd be able to get through it all in a 12-day trip. Along with this pretend itinerary I made multiple notes about my must-see destinations.

Notes, notes, and more notes on Iceland trip ideas!

4. Pre-booked a rental car, flight plan, and a few hotels, to get an approximate cost estimate before cornering Joey and forcing him to agree that Iceland was the right choice.

5. Researched the national language of Iceland and learned some preliminary necessities (hello, goodbye, how much does this cost, where is the bathroom, can I have a beer).

6. Calculated the conversion rate between the Icelandic krona (ISK) and the Canadian dollar (CAD), and created a budget for the trip.

I love the power of the Internet for research!

After all of this obsessive behavior, my husband realized the trip was most likely going to happen with or without his blessing, and he booked the time off work. This allowed me to do what I had been dreaming of doing since November: I hit 'BOOK IT' on the Expedia website and formalized our trip plans!

Now, I am compiling all of my data and research into a Google Docs PowerPoint (yes I know, here's where it gets REAL nerdy) and am in the process of nailing down the details.

Making travel PowerPoints makes me feel organized and oh-so-excited!
This includes booking the bus from the airport to the Blue Lagoon and then to our hotel in Reykjavik (check).

Headed to the Blue Lagoon in July - yay! Image courtesy:

This includes booking the rental SUV to tackle those bumpy highland roads (check).

This includes booking our tour of the Golden Circle outside Reykjavik (check).

Gulfoss in the Golden Circle. Image courtesy:

This includes booking two hotels for the first six nights of our trip as we drive around the southern lip of Iceland (check and check). 

And this is where Joey stepped in. "Why don't we just see how it goes when we get there?" he asked when I expressed frustration over the fact that most hotels were full or sold out. (On a side note, one of the Icelandic B&B owners told me that big travel companies block out entire hotels or sections of hotels for their tours, then release the unsold rooms in the late spring. If you are having trouble finding rooms on the island now, try again in late May.)

Reykjavik from above. Image courtesy:

Remember that note I mentioned above, about two travel partners having to be similar? I myself need to be reminded of that from time to time. For the second half of our trip, while I still do have a list of things to see and do, I am going to try to flow with the ebb and tide of travel. We will talk to the locals and get their take on what we should experience, and try to find places to stay as we go. I sure hope it works - I wonder how much divorce costs in Iceland? Just kidding!! Wish me luck!


  1. I can see how much fun the planning ahead is, but truly, it is the unexpected that comes on your path that will leave the biggest impact! leave some room for the unexpected! there are so many beautiful little villages to discover, little fish markets, local stores and restaurants...for the Icelandic people it's their normal,so they won't advertise for it, but it will all be new to you so allow yourself some time to be surprised!A bit of both, that's exactly the way to go!

    1. I know, I know - I am trying to get better! That's why I haven't fully planned the latter half of this trip yet. I'm hoping to 'go with the flow' a little more.

  2. This post made me laugh. I'm a bit of travel planner too, so I completely understand the travel planning. One reason why I love travel planning (aside from the fact that it's fun) is that helps me get excited for a trip, and it helps the trip become more "real" than if I just had a ticket and showed up somewhere. I do know that I can't plan everything either. There's going to be something that comes up and changes your plans, so I've learned to roll with the punches in my travel a lot more than I used to. Honestly your trip to Iceland sounds like it's the perfect combination of travel planning and spontaneity. I wrote about my travel planning ways a while back here:

    1. Exactly Alouise! I get so carried away, but like you, planning makes it real and concrete for me. It's like having a dream come true scenario actually coming true! Can't wait to read your post and compare our styles... ;)

  3. I enjoyed reading this post very much. I'm just like you, I have to plan plan plan trips, if its not making endless lists it's researching, reading various travel blogs etc. It's nice to know there's others out there :) I've previously been to Iceland twice and have another trip booked for May so I always love to read about other peoples experiences and things they have planned. The last time I went, my partner and I drove the ring road of the country as I see you are doing too. There is so much to see and do. If you have any questions about our itinerary we took etc then I'd be happy to help. My partner is actually Icelandic (living in the UK for over 10 years) so that helped us a great deal :) Here's a link to some of the photos we took:

    1. Oh yay! I would LOVE to connect with you and get some ideas and details about traveling in Iceland. I want to go up to the northern section and see the Stone Rhino in Hunafloi Bay, but I'm not sure exactly where it is or where to stay. Let's connect on Twitter - my handle is @thewrabbithole I'd love to hear your stories!

    2. Followed you mines @lynscp :)

  4. I prefer planning out my travels as well! Because of various confusing reasons, I ended up going to Tokyo with absolutely no plans and little money. It was really not that fun, because apparently all the neighborhoods close everything down on different days, and we kept going to places on those days by mistake. We had no idea what there was to do, and we had very little money, and the people we were staying with practically refused to give us any tips. Next time, I'm having an itinerary!

    1. Ouch! Hopefully you figured out all of the routines and were able to navigate the city after a bit. I can't believe your hosts didn't help out more! But thanks for helping me to emphasize my point - it's NOT nerdy to plan ahead! :)