Trip Planning: An Introduction to Wandering Like a Weirdo

Hello World! I’m the travel counterpart to the one and only Wandering Weirda and my biggest contribution to our travels takes place before we get on the plane (Spoiler: I’m talking about trip planning). Over the years, I’ve spent a lot of time refining our process to go from looking at pictures of amazing destinations to getting tickets booked and bags packed — and now I’ll pass along my words of wisdom.

Overall my hope is that you might be able to find something from our experiences that enhances your next trip!

So, let’s talk about planning. It’s not everyone’s favorite part of a trip (in fact, the Wandering Weirda was once all but useless at this stage), but it has to be done at some point. Even if you don’t take the time to put together a plan prior to the trip it will eventually become some form of planning on the fly — in other words, this is when you increase your chance of ending up in a tourist restaurant paying double or more for mediocre food. Planning ahead doesn’t mean everything will go perfectly, but planning to a level which suits your travel style greatly increases your chances of having an enjoyable trip. The worst possible outcome of a trip for me is a feeling of having missed out, or coming back saying “I wish I did X.” Having expectations and a plan in place prior to departure has really helped to minimize those concerns and has led to some amazing experiences.

If you already love planning, that’s great! If you don’t, then it is important to remember that different people need different levels of planning. Planning doesn’t have to be a daily itinerary with every meal and activity booked and listed out in 15 minute increments. It really comes down to what degree of pre-planning you are comfortable with. Over the years, our planning style has evolved to include the following:

• Choose destination, dates, and book plane tickets
• Book accommodations and consider travel logistics
• Research activities and restaurants
• Book the must-have activities/restaurants

From here, you can adapt your plan to include more or fewer items, but my rule of thumb is to plan for anything which you would expect to make you nervous or stress you out. One example of this (for me) is figuring out how I am going to get from the airport to my first night’s accommodation. In the US this is usually just Uber/Lyft/Taxi, but abroad it really helps me to know the expected taxi fare or which bus/train I need to locate.

With all of this in mind, I’ve done my best to break down my thoughts on overall trip planning into 5 key areas:

1. Defining your travel style and expectations
2. Picking a destination
3. Booking transportation and accommodations
4. Planning activities
5. Taking the trip!

As you can probably tell by now, trip planning is topic that I am very passionate about: every hour spent on planning or research ahead of a trip is more time that I can devote to exploration or enjoyment during the trip itself. In the next few weeks, I’ll be writing in-depth posts about each of those above topics and am really looking forward to hearing your thoughts on how you prefer to plan trips!