Trip Planning: Picking a Destination

Kylee Hayes Travel Planning 2 Comments

How do you choose your destination? This might seem like a silly question, but it’s not. People ask us this all the time. So many people want to travel and explore the world, but don’t know how to begin. When we tell them “Just pick a place,” they often freeze up. Suddenly the world seems much bigger, and trying to narrow down a specific city or country or region becomes a daunting task. So how do you choose where to go?

The easiest way to choose your destination is to start with these questions:

How long is your trip?

How many days do you have off from work do you have? Do you want to use all of those days to travel, or would you like to be back a day before to get everything in order before heading back to work?

If you only have a three day vacation, you likely won’t be picking a place with longer than a five-hour plane/boat/bus/train ride. That is five hours there on the first day and five hours back on the last day. Not to mention adding in the time of prepping for the trip (check in for a flight, pre-boarding screening line-ups, bag drop off, etc.). If you’re determined, it’s certainly doable, we just don’t recommend it.

Of course, the more time you have, the further you can go without being rushed. So that should narrow it down. If not, skip to the next question.

How much do you want to spend?

Are you saving up all year for this one trip? Do you have a set budget in mind? Budget is often the most critical factor when picking a destination. Understanding how much you are able to save and what you’re willing to spend will play a significant part in your destination choice.

Flights are almost always the most expensive part of travel, regardless of your style. So logically, the farther from home you want to go, the more you’ll need to budget. Once on the ground, the general daily living costs are your next concern. Say you’re from North America and have a budget of $2500. Flying to Dubai for a week would be doable, though you’ll be tight on cash. Backpacking Latin America for a month, however, you could come home with money still in the bank!

Check out to get an idea of how much things cost while you are there. Europe is going to cost much more overall than Asia or Central America. So depending on your budget, you can go for a shorter trip to a more expensive country, or a longer trip to a more budget country.

A wooden dock over a lake with colourful houses in the background.

By Backpacking in Latin America, we were able to travel for many months on a very tight budget!

What time of year are you going?

Is it hurricane season where you want to go? Is it a hot, dry season or a wet, rainy season at that time of year? Are you going for a ski vacation?

We love to travel in shoulder season, the one or two months before or after high season for that particular destination. This is because there are usually a lot less tourists, and the prices for accommodation are usually cheaper (or you can ask for discounts.

However, it doesn’t always work out with your travel plans. Visiting Mallorca in the shoulder season was great for car rentals prices, but the water was way to cold to swim, and many of the restaurants were closed. So while we saved a bunch of money and got some great photos, we weren’t able to enjoy those spectacular Mediterranean beaches.

Then again, as cheap as Thailand might be, visiting during their dry season means higher prices and bigger crowds. Sometimes dealing with a little rain is worth it.

What kind of Activities are you Looking For?

What are some of the main reasons for your trip? Are you looking for beautiful architecture and history? Europe should definitely be high on your list. Planning a culinary adventure? You should be leaning somewhere with a well-established and vibrant food scene. Maybe Thailand, Mexico, or Italy. Adventure travel? Bungee jumping in New Zealand, surfing in Costa Rica or paragliding in Medellin.

Think about what you want to do while on your journey and look into some of the worlds best destinations for each. This is a definite way to help you choose your destination.

Also, is it the right time of year for what you want to do? Going whale watching in the wrong season would be a big let down.

And now that you’ve given it all some thought and you have a destination or two in mind, it’s time for the final question:

Is it Safe to Visit?

Political unrest is a real thing. Check out the government websites to see what is happening in the country you are headed to make sure you are making the right choice. Check out these travel advisory sites:


If after you have read this, and still cannot narrow down your results, contact us. We would love to help you pick the perfect destination for YOU! If you have figured out how to choose your destination, CONGRATS! Check out more of our travel resources to see what you need to do next.

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1 year ago

Great tips. I have a list of places I want to visit but usually the decision is based on flight prices. Sometimes you can get them really cheap for a destination you never thought of and you fall in love with it. For me that was Taiwan last year. Never thought I would go there but then the opportunity present itself and it was amazing country to travel.

1 year ago
Reply to  Janja

That sounds like a great way to do it! As Canadians, we rarely find “cheap” flights, but it happens from time to time!

Where are you located? Does this happen often for you?