How To Pick Your Next Travel Destination [New for 2019]

Not sure where to book that next trip to? Or do you have a few vacation ideas but don’t know which to roll with now?

Well, I’m glad you’re here now because this article is your definitive guide to choosing your next destination…

Not only will we spark your imagination and amplify your urge to jump on a plan, but we’ll also fill you in on the smart reasons why certain destinations might be a lot better pick for YOU than others (and they’re probably not reasons you’ve considered).  

And remember, one of the best parts of not having any current travel plans is that you have a blank slate… 

…you can go anywhere in the world you damn well please. Or, as Scarface would say:

Everyone’s finances, luxury levels, and reasons for travel are different. So we’ve put together this guide to help YOU choose, based on factors YOU care about. Scroll through and dive in where fitting! 

At its core, this breaks down to five main avenues you can take in choosing your next destination: 

  1. Bucket List It
  2. Experience Based
  3. Friends & Fam
  4. Event Based
  5. Price Based 

To help nail this down, we’ve curated the best resources around each avenue to spark your imagination, make you drool, and open your eyes to new places you may have never considered. 😮🤤 Let’s start with old faithful…   

Bucket List It

Do you have a bucket list? Even if you don’t have one written down, is there a spot that you’ve always dreamed of going? If so, that might just be the destination for you to shoot for REGARDLESS of how expensive you may think it is… 

Life is short. Don’t save the good bottle of wine, eat dessert first, and sure as hell do NOT put off exploring the one place on earth you’ve always dreamed of going (plus, in a couple of days we’ll show you how to travel for a LOT less). 

Need some initial inspiration to get your list rolling, here are 18 Incredible Bucket List Vacations To Add To Your Checklist

(Want a fun way to write and track your bucket list? Check out our Life Listr app.)  

Experienced Based

Maybe there’s not just one place that you’re jonesing for right now, but one type of experience instead?  

Maybe that’s sailing some islands, or snowboarding, or hiking, or history tours. Whatever the experience is that gets you the most jazzed up, think of the best places in the world to do it and go from there. 

We spend a lot of time putting together “Best Of” lists on the blog because they spark a fire in people to travel and our readers love them.  

So, here are some of our “experience” lists, as well as one from another site… all of ’em loaded with ideas for you to daydream over:      

For La Familia

Maybe you want to reunite with a friend you haven’t seen in years. Well, go and see them! Or as I like to do with my Aussie buddies, plan to meet up somewhere new in the world you both haven’t been. 

Or do you want to take the kids to meet relatives, or for them to have a certain experience, see a certain site? Maybe it’s just you and your partner, and you want a romantic, fun place to spend time just the two of ya? 

Or perhaps you’ve got a furbaby and want to know the most pet-friendly spots? 

Whatever it is, traveling for your people will never let you down. To help, here are a few links for inspiration:      

Event Based

Want to throw tomatoes at strangers in an all out, city-wide food fight? Well, La Tomatina happens in Spain only in August every year. 

Want to see an English Premier League game? Or dance for days on end at Trinidad Carnival? Event based trips are a phenomenal choice for a trip too… especially since our best memories are of the experiences we have when traveling. 

Check out these posts for a few ideas:      

Priced Based

Price based travel is a big thing — as it should be — because if there’s any budget involved you can get a LOT more in some places, or at certain times of the year, or even based on how their economy is faring.  

I think we all inherently know this but the idea of this solidified for me a decade ago when I stumbled onto The Four Hour Work Week, by Tim Ferriss…  

… and the timing could not have been more perfect because I was broke as a joke and had the travel bug, BAD. 😬 

The book introduced me to a concept called “geoarbitrage”. It sounds like a complicated term but the premise is simple: take advantage of the fact that your country’s dollar is worth more than other places in the world. 

For example, if you were to pay $2,000/month in rent in a major US metropolis, that same $2,000 could have you living like a king in Bali for six months (I haven’t been to Bali yet but this equation was confirmed by a Canadian buddy who runs a successful clothing line out of Bali). 

Here’s another: $100 USD could get you one night at a decent Airbnb in Reykjavik, or 2 nights at a fantastic hotel in Lima. The same beaner gets you double in a country like Peru than it does in Iceland. 

The same applies to all countries in the world. So, it’s a wise decision to use this to your advantage so you can travel more often, AND up the luxury of your trip. Here are some resources to help:      

I do believe that’s probably enough to explore, imagine, and pin down your next destination. Now, have some fun with it! 

Here’s to you, amigo, for living the width of this life, not just the length of it.

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