Planning That Trip

Everyone has their own methods to planning a trip. Some want everything to be perfect prior to putting a single dollar towards it, others throw caution to the wind and let things fall where they may. I’m the second type, I will jump in feet first and worry about the finer details later.

Below is a quick summary of how my planning goes.

Time Management

Being single, with no real responsibilities, I’m quite flexible with my time. I do have busy periods at work which I try not to travel in, and of course hockey season, but these generally can be worked around. This leaves me open to grab opportunities when they arise.

Bucket Lists

I have a bucket list, not on paper, but in my mind. There are places I’ve always wanted to see or have inspired me, so if someone mentions that they are planning a trip there and ask if I want to go, bon voyage!

Life Events

Let’s face it, I have dropped things to make a short trip to the USA for a friends wedding I didn’t want to miss. That same year I travelled for three weddings, and the one wedding that was in my hometown I couldn’t attend due to attending one on the other side of the world. I try my best not to miss these important occasions, and plan a bit of sightseeing around them. When I do miss a milestone, an engagement, birth etc. I try to send a postcard from where I was that day to say I was thinking about them even if I wasn’t there to share it with them.


The first thing I book are the flights,  generally, these are the most expensive part of travel and what the rest revolves around.  Although,  sometimes this isn’t always the case, and I have just booked a tour through Vietnam without yet booking my return flight (I’m still deciding what I want to do).

Then comes research and compiling a rough itinerary,  then depending on the location and season whether accommodation needs to be booked in advance. When booking rooms I prefer to use simply because you can choose free cancellation in case things change, quite often no prepayment is required and I have never had an issue with any booking (even getting upgrades on occasions).

Also,  check out if there are any must do sites or day tours and save your place early. Generally, I research the day tours and see if I can replicate or do a similar thing by myself. This means I see more of what I’m interested in and less of what I’m not. However,  some sites are via organised tours only or at least pre-arranged bookings, think the Vatican, the Uffizi, Alcatraz in summer, another is Antelope Canyon in the USA. These places generally sell out weeks in advance (depending on season),  so as soon as you know the dates do some research and if needed book your place. Also, some museums and art galleries have free access nights, so check up on these too, as it is a great money saver.


By this time, my savings are probably on the low side so I need to put in an action plan to get some money together to enjoy the trip (I don’t like worrying about money while I’m away).  I have a travel card that is used only for travel and therefore put money into it regularly whether I’m planning a trip or not. Whenever I get some extra cash I throw it into that card.

Late last year I started a different savings plan, of sorts. Acorns is an app which rounds up your purchases and when you reach $5 it will invest it into the stock market; for example, buy a coffee for $4.50 and $0.50 is invested (saved) for you.  Think a term deposit without a minimum deposit or time restraints; you can deposit as little or as much as you like and can access your money whenever you need it (do allow a few days for the transfer though). I’m loving it, the money builds gradually without me realising.


Depending on where or when you’re travelling and what you are doing, you may be required to make specific purchases; that down jacket for cold weather, or walking poles for that hike. I make a list of these “essentials”, do some research and then keep an eye out in my inbox, newspaper etc. for any sales that come up, then just head out and buy. Alternatively, do some research to see if you can purchase once you have arrived at your destination without too much hassle; this works particularly well if you’re after snow gear and live in a Mediterranean climate, where choices are limited and prices are high.

So that’s a bit about my planning process for trips, I hope these help, or if you have any of your own tips let me know.

*** Disclaimer – please do your own research prior to signing up for Acorns, it suits my situation, however, it may not suit yours. ***