On the Fly Planning

Posted by Madeleine Kennedy on

I've come to the conclusion that I am a "do-er". I just do things. Sometimes I get caught up in the cycle of perfectionism and it too can eat me alive, but most of the time, I'm just doing things. Like right now, I'll post this and probably not edit it. I'll write it and done. That is part of my "do-it" attitude. 

This translates into my travelling. Ever since our first big trip in 2010, we never did too much planning. Maybe I should say rather, never too much scheduling. We planned, we researched and we knew things we wanted to do or places we wanted to go. We just didn't know when or for how long and the how behind it. 

I think this has been a blessing and a curse. I think the do it attitude is good in travelling. There have been a number of times it has totally worked in our favour. It worked out on our last trip to Peru, we would have planned an extra flight and city had we gone with initial thoughts but opted instead to chill in the Sacred Valley. That worked out. It also worked out last winter when we spent six weeks in South East Asia. We had flown to Hong Kong and anticipated a trip to the Phillipines, being one of the few countries we have yet to travel to but instead we ended up in Myanmar because of bad weather in the Phillippines! So that totally worked out. 

It has also not worked out. Like the ONE time we had our wicked friends fly across the world to meet us in Koh Lanta, Thailand. We regailed them with tales of walking up to our Beach Huts to find the most perfect accomdation. However, when we all arrived to the Island, turns out it was Chinese New Year and there was NO WHERE to stay. It was uncool. So, it isn't always a fairytale, for sure. 

What I would say is, just wing it. After so many countries visited here are the things to keep in mind: 


1. There will ALWAYS be somewhere to stay. It might not be the most instagrammable, but regardless, you'll be fine and have a cozy bed at the end of the day. 

2. Know where you want to be. Search out the beach or the neighbourhood you vibe with first and foremost. From there, show up and visit your top three spots. Usually a better price is had that way also. 

3. It's worth it to vet a few places. Sometimes one of us will chill while the other goes and checks out hotels. It makes it easier when you split the task. 

4. Always negotiate if you are booking IRL. The longer you stay, the better the deal. 

5. Stay open. Talk to people and find out where they just came from or are headed to. This has worked out for us a million times. My favourite places we've been to were always recommended by another tourist or local while on the road (beach). 


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