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How To Plan A Trip

How To Plan A Trip

Follow these 10 steps to get the hard part off your plate

By Spencer Selhi

With the busy pace of life we’re all experiencing these days, planning anything can be stressful. Unfortunately, making sure you’re organized for a trip can put a downer on your journey before you’ve even left home.

I follow a 10-step approach when planning my trips, and it hasn’t failed me (yet!). Keep in mind that this is the perspective of a left-brained, male pilot. I know all too well that many people might prioritize differently. If so, please share your approach in the comments.

With that said, here’s what you need to do to ensure you have your bases covered before a trip:

1. Figure-Out Where, When, What, and How

The most basic step, to say the least, but everything starts here. Perhaps these choices are all up to you to make, or perhaps you don't have much control over these things. Either way, you can’t plan anything else without knowing where you'd like to go, when you'd like to go there, what you'd like to do while you're there, and how you'll get there. Everything else can start to flow once these things are settled.

2. Determine Your Budget

This should be self-explanatory. Even if you don’t need to budget for travel, you should create a budget anyway - it’s a good habit that will likely help you in the long run. You don't have to be overly specific when setting a budget, however, it does need to be realistic.

3. Identify Your Travel Window

Are your travel dates fixed or flexible? If you can adjust your dates a little at either end of your trip you might be able to save a little on flights. Also keep in mind that you might not enjoy a shorter trip as much, and that you will incur additional costs for every extra day of travel you decide to add last minute.

4. Book Air Travel

A quick search for “when is the best time to book flights” reveals about 100 different opinions on the matter. My advice is simple: book as soon as you can with as few connections as possible. Your future self will thank you.

One quick note before you complete this step: if you’re traveling internationally, confirm the visa entry requirements of where you’re going. You want to ensure you have sufficient time to get a visa (if necessary), otherwise you will be denied boarding if the country at the other end requires you have it in advance.

5. Identify Key Activities and Where (Geographically) You Want to Stay

This step is an important one. If you’re like me, you don’t want to spend all your time commuting - you’d rather spend it experiencing your destination. Once you identify where you want to spend most of your time, find accommodation options that suit your needs within a reasonable distance.

6. Book Accommodations

Similar to booking Air Travel, you could spend hours trying to find the best price at the perfect hotel. Each travel site will offer different star ratings, prices, and reviews. I suggest you book accommodations with a favorable cancellation policy, and book early. That way, you’ll have the option of changing the booking if you find something better later on.

7. Plan a Rough Local Itinerary and Book Essential Local Travel

Now that you know where you’re staying, you can figure out how you’re going to get around. My last trip to China was seamless because I took a little time to think through travel at the destination. Whether it’s a rental car, transit, or Uber, having a rough itinerary and knowing how you’re going to get around will make life easier at the other end.

8. Confirm Local Climate / Anticipated Weather

Knowing the climate and forecasts helps to minimize weather-related disappointment, and will help you when it comes time to pack. Hot+dry equals lighter outfits; cold+wet means layers.

9. Identify “Must Haves”

Now we’re coming to the end of planning and transitioning to preparation. With what you know about your itinerary, hotel, and forecast you can determine what you absolutely need to take with you. Clothes, credit cards, and identification are a given; this is where you identify items such as equipment or medication that is not readily replaceable, and would ruin your trip if you forgot them.

10. Identify A Worst-Case Scenario and Work Through It

The last thing I’ll do when planning a trip is think about a likely worst-case scenario. I'm not referring to "end-of-the-world" type of scenarios but rather something more along the lines of "what would I do if I lost my passport" or "who would I contact if I missed my connection"? When you have a plan for what to do when things go wrong, you’ll realize there’s a solution to every problem so there’s no point in worrying about things you can’t control.

Finally, if time is on your side, you can create excel spreadsheets and PDF documents to track everything and keep information such as reservation codes handy at all times. I do this for bigger trips where I want to make sure everything runs smoothly, however, most of the time I prefer to just make sure the big pieces are in place and figure the rest out as I go. There are, of course, apps and services that do this as well, but I haven't found the process to be complex enough to automate (yet!).

What do you find helps when planning a trip? Please share your ideas in the comments section below, or send me a quick note:

Travel thoughtfully,


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