Planning: 3 Big Decisions


If you’ve got your passport and the travel bug is biting, you may be tempted to start booking hotels. WAIT! If you don’t want to go back to the drawing board with each decision you make, you need to build your trip a solid foundation. The way to do that is by thinking through your 3 biggest decisions.

1. How much time can you spend?

2. Where do you want to go?

3. What season do you want to go in?

The first question always hits us the hardest. It’s like you can hear your parents in the back of your head yelling “you’re not going anywhere until your room is cleaned.”

Obligations, ugh. Whether it’s family, work, school, or something else, you likely have a limited amount of time you can take away from your everyday life for a trip. We hope it’s a lot, but even if it’s just a little, we’ll help you plan so well, you’ll get the most out of every hour.

So here’s the first thing you need to do. Come up with a hard number of how many days you can be gone. We’re talking the maximum number. Don’t play it conservative now so you can add in some days later. Knowing this number is going to help you set some boundaries on your trip. Write it down somewhere, maybe even on the top of the Trip Brainstormer in the back of this guide.

Now, aren’t you glad that’s over? You’ve got a number. It may not be the number you wanted, but at least you know what it is and now you can fill up that time with some memories that will last a lifetime. And you’re about to feel even better because now you’re going to decide where you’re going. At almost the same time you’ll be considering, what season to go in.

Is the place you want to visit and the season you want to visit in conducive? Maybe a better question to ask would be, will the place you want to go to be the way you want it when you get there? We’re all about seeing places in every season, but if you’re dreaming of ice skating beneath the Matterhorn or dancing on a grassy mountain in the Austrian Alps (which were both Ryan’s dreams) then you’ll need to pick the right time of year.

So you’ve got a trip duration, you’ve got a travel season, and you have a destination. First three decisions are done, right? Not so fast. We want to challenge you to think creatively. Let’s take that destination you have in mind and see if we can turn it into something bigger.

Fire up Google Maps and take a look at where you’re going. Now zoom out and see what’s around it. Are there some cities or natural attractions in the vicinity? Use the directions tool to figure how long of a drive or train ride they would be. For us, we’re good with a three hour car ride or a five hour train ride. Anything more and we feel like we’re missing out on good vacation time. We also like to spend at least two days everywhere go. It’s rare for us to check in one day and check out the next (al- though sometimes it makes sense). So, is there a natural path of destinations that would take you from one major city to another with reasonable travel times between stops?

You don’t have to know how long you’d spend in each spot yet, we’re still just nail- ing down where you land and where you take off. Just treat it like a math problem. If you have 10 days to travel, you want your total destination count to be five or less. Are there five or less places that are less than a three hour car/five hour train ride apart that you want to go to? This is how you turn your trip to Paris into a full on Western European excursion.

We’ll give you an example of a time we did just that. We were going on a summer trip Europe. We had 14 days and we knew we wanted to go to Paris. But we also wanted to add a little diversity to the trip. There was a vague idea floating in our heads of maybe going somewhere in the Austrian Alps. But the Alps are too far for a train/ car ride to be comfortable (for us).

We looked on the map and saw Zürich lying there between Paris and Austria. It’s only a four hour train ride. We started to day dream about chocolates, cheeses and clocks. We pulled up some pictures, like the one on the cover of this guide, it’s amazing. We saw people swimming in the river, cruising on the lake, fonduing all over town. We were sold.

Next, we checked the distance to the Alps. It was only a three hour drive. Perfect. We picked a town out that seemed exciting to us and that seemed to have a healthy selection of hotels (we’re not picking hotels yet, but you always want to pick a destination with options). We wanted to fly out of a major airport to avoid a ton of connections. So we knew we’d be going from the Alps to somewhere else. Vienna sounded ex- citing, but it was a six hour trip. Venice and Milan were both about five and half hours. But Münich, Germany was only three hours away. Beer gardens bratwurst? We approve.

So now we had four locations on our list. Each no more than a three hour car ride or five hour train ride apart. A minimum of two nights in each place would be eight nights and we had fourteen days to work with, so we knew we were good there. Our trip to Paris just became a four country western European excursion.

We’re not saying you should always do this. Some trips don’t lend themselves to multiple destinations. Some times you just want to get dropped off at the Sandals re- sort, work your way through a truckload of Piña Coladas, and fly home six days later. But we do think you should consider it if you want to make the most of every trip you take!

With that said, don’t give in to the temptation to start picking hotels and listing out activities yet. At this point, you have your passport, you know how long you can be gone, what season you’re traveling in, and you know where you’re flying into and where you’re flying out of. The next step is booking your flights!

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Tips, PlanningStephen Reed