Planning Your Trip: Choosing a Destination

Hi! Despite having a LOT of past trips to catch up on, I thought I’d change it up today and give you a peek into how David and I plan our trips. Actually, it’s more how I plan our trips. David mostly hates this part.

And he’s not alone! Lots of people out there get stressed out just thinking of how to plan a vacation. Too many details to worry about! I’m definitely not one of those people who obsessively plans every activity and route. We keep our vacation days pretty flexible. But there are definitely a lot of considerations. Trust me, I get it. So, I’m starting a series on trip planning! I’m hoping these posts will help.

Trip Planning Part 1: Choosing a Destination

Most people won’t need any help coming up with where to go. In fact, they may need help paring down a long list! This is especially true for those people whose vacations are few and far between, for whatever reason. “If these two weeks are going to be the only real break I get this year, they damn better be perfect!”

When are you going?

This is the easiest question to answer for most people. Work and school schedules, family obligations, holidays… all things to take into consideration.

David and I like to take our big vacations during our birthdays. However, David is taking some classes and his birthday will fall in the middle of spring term: not an ideal time to take two weeks off. So, we’re going during spring break! No, not that spring break… we’re not partying in Cabo with the teenagers, thanks very much. We’re talking about the end of March/beginning of April.

So, then we look at our list and narrow down where it is best to go at this time of year. We actually prefer to go in “shoulder season,” which is the time just before or after a place’s “peak tourist season.” So for example, many people want to go to Germany for Oktoberfest. Definitely a cool thing to experience, but you can bet flights and hotels will be expensive and there’ll be tons of people. I’m too poor and too much of an introvert for that! So I would go there in September or November.

However, David has been dreaming of spring in the Netherlands. And since we’re going so far, we might as well see more than place (we call them scouting trips). So we decided to travel down and check out Brussels and Paris as well. I know, there’s a lot to see in that area, but we can always do a return trip later on!

What do you want to do?

Want a chill vacation? Find a beach area or take a cruise. Want an adventure? Check out ski spots, or surfing, or maybe even an African safari. Is it an occasion like an anniversary or a honeymoon? Research the most romantic places in the world and pick one. The kind of trip that you want will narrow down your options and help you choose where to stay and what activities to consider spending on.

Want a combination of some or all of it? Google that!

Read travel blogs (like this! =D) and ask your friends. Sometimes people might mention places you never thought of. For instance, Turkey is generally not a place most of my friends have on their lists, but I love telling them what a wonderful experience I had there. And once, on a plane to Maui, my seatmate told me all about an amazing hike. I’d been to Maui a half dozen times and never heard of it, and it’s the best thing I’ve ever done there.

How much can you spend?

We are not all millionaire celebrities who can spend a month lounging in a private beach on Bora Bora. So, when thinking up a destination, consider a ballpark budget.

Your biggest ticket item is most likely going to be your airline tickets. With that in mind, go on Expedia or Hotwire and scope out flights to your chosen destination around your travel dates.

And take an insider’s word on it: tickets on Tuesdays-Thursdays will likely be cheaper than weekends. Also, book over a month away if you can; most airlines use tier pricing depending on how far in advance you are booking. This won’t work for a popular destination like Hawaii during Thanksgiving, for example, so if you’re going during any holidays, be prepared to fork out some cash for your flight.

Do the same thing for hotels. Or check out sites like AirBnB or VRBO where you can rent places from locals in the area. Remember, we’re not picking out your actual hotel yet (I can be pretty picky about where I stay, so this is usually what I spend the most ‘planning’ time on), just getting an idea of how much things will cost. If you are okay with couchsurfing, then keep that in mind as an option too!

Finally, look at the conversion rate between your country and where you’re going (if your trip is going to be international). You typically will want to go to places where your currency is stronger, but that’s not always possible. Few currencies are stronger than the pound sterling, for example. But you want to find out how much you would possibly spend on food and transportation each day.

After you’ve checked these things out, add up your amounts and see if you are prepared to spend that much. High estimates are okay; in fact, they’re probably better because you’ll end up with more pocket money in the long run. Plan to save that much, or make cuts where necessary. For example, on our upcoming trip to Europe, I can expect to pay about $120/night for a 3- star hotel in Amsterdam, $80 in Brussels, and $150 in Paris. Ouch, that’s gonna hurt on a two-week trip. It looks like I may have to lower my standards when it comes to hotels.

Maybe at the end of it all, you decide you really can’t afford to spend $1700 on hotels for two weeks. Then you might consider an alternative trip. Perhaps Paris will have to wait, or maybe you want to try Eastern Europe like Prague and Budapest instead where things are slightly less expensive. And that’s okay! There’s a fantastic trip waiting out there no matter where you go, and it’s up to you. If you’re worrying about the immense credit card debt you’re racking up, you’ll spoil your vacation.


I hope these tips are useful to you. Maybe you already know them and have more ideas, feel free to share those below! Next month I’ll have more trip planning advice. Stay tuned!

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3 thoughts on “Planning Your Trip: Choosing a Destination

  1. We toss around ideas while eating dinner at night. I try to keep a running list in my head of all the ideas but some times they are pretty vague. Husband said a few years ago, that island in Texas???? What???? Ends up he meant South Padre and it was a great trip, great idea once I figured out what he was talking about. LOL!

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    • There’s an island in Texas?! Haha. Yeah sometimes we’ll run across a photo or something that looks amazing and just say, “That’s going on the list.”

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  2. Pingback: Travel Planning: Where to Stay | World and Time Enough

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