One of the hardest parts of travel is deciding where to go in the first place.

When the world is so enormous and the destinations so numerous, it feels like we'll never see it all. In truth, we most likely won't see it all. So we are left with picking and choosing what we can manage in one lifetime.

If you're like me, you like to be as informed as possible when making any decision.

So for the thinkers, the planners, the people who used to be indecisive but now they are not so sure, this post is for you. This is your guide to the practical considerations for making the most informed decision possible about choosing your travel destination(s).

Do What's Affordable or Hack Your Way to Affordability

The cost of flights and accommodation alone may determine your destination. And that's okay! Do what is within your means—but also know that travel does not have to cost a ton.

What seems impossibly expensive can be made inexpensive with a few tricks. Use my travel hacks to help you think outside the box and travel on a budget.

For one, airfare costs a ton. Unless you live in the USA and have followed my guides on earning and using airline frequent flyer miles, you are probably like most others who have to pay in full for airfare. If that is the case, then you'll want to find ways to make your trip more affordable all around.

A view from the window on my flight over New Zealand

Start by signing up for flight alerts on websites like Airfare Watchdog. This site will tell you when flights to a destination you have your eye on is at its lowest by industry standards in a given timeframe.

Alternatively, use Google's ITA Matrix Airfare Search to identify the least expensive flight options for your travels. I also love to use Google Flights because of their excellent advanced search options.

Master tip: Do not book through travel sites like Expedia. Just don't. If you find low-cost flights on American Airlines through Google Flights, for example, then go to, search for the same flights, and book there. It's almost always less expensive.

You can also employ a simpler travel hack for lowering the cost of your flight. One of these is purchasing a ticket to a destination that has a layover at your intended destination. A ticket like this means you would get off the plane and leave the airport at the layover destination and "miss" the last leg of the flight path. Often, these layover flights are less expensive than paying for the flight that goes direct.

For accommodation once you arrive, try no-cost housesitting or couchsurfing. If neither of these are your style, look into a low-cost stay through a website like AirBnb. Better yet, tap your network of friends and family. There may be someone you know or a friend of a friend willing to host you.

Consider Time Frame and Distance

Peering over the airline seats at the world map

One common mishap of travelers to new destinations is underestimating or overestimating how long it will take to get from one place to another. This includes both the time it will take to travel to the destination and between destinations within the country.

Don't forget to consider time zone changes when you travel particularly long distances. If you travel East to West, you will lose hours or go "back in time." If you travel West to East, you will gain hours or go "forward in time."

Jump the international date line and you could gain an entire day in the matter of seconds like I did when I visited Niue from New Zealand. I lost a day on the return trip to New Zealand.

Sometimes concentrating on one area of the country is better especially if you're visiting a large country like Australia or Canada. You'll lessen the time you spend traveling from one location to another by staying put and/or making short, day trips in the surrounding vicinity.

I like to use Free Map Tools to determine how far I can travel by car from one destination in a set amount of time. Enter a city, the average speed you will drive, and the max number of hours you are willing to travel outside the city. This tool will give you a map representation of the area you can cover.

If you're planning a multi-day road trip, use Google maps to estimate travel time. Use a gas calculator like Fuel Economy to determine if the money you will spend on gas will outweigh the cost of a flight to the same destination.

Flying can shave off several hours especially in some of the bigger countries. For me, road trips were worth the extra time and sometimes the extra expense because it meant I had more freedom.

Master tip: Google "transfer car" websites to significantly lower the cost of your ground travel. If you need to do a round trip, you can always book two separate transfer cars from point A to B and then B to A.

I carefully mapped out my road trip from Melbourne to Cairns in Australia using transfer for a free 10 day car rental. After considering the above, I figured out the trip would be the equivalent of driving from New York to Salt Lake City. Although the gas was a bit more than the cost of a flight, I got to camp and see a ton of sights along the way.

Look Up the Weather and Temperature

A sun-soaked drive around Iceland

I researched the months for rainy seasons and cold seasons for each destination I had in mind. Then I mapped out a path that would allow me the chance to "chase the sun" and avoid the serious rains (e.g., monsoon season in Southeast Asia).

For example, the sunny weather I had driving the Ring Road with my travel companions in Iceland had nothing to do with good luck. Before our departure, I tuned into the Iceland Met Office to get the most accurate forecast for the nation's weather.

The Met Office's handy map shows temperatures and conditions for the entire country for the upcoming week. When clicking ahead, I could see that the sunny days went naturally in a counterclockwise circle from one day to the next. So that was the path we took.

Master Tip: When you can, use the country's own weather service for the most accurate information.

I knew I'd eventually catch up with winter by staying in New Zealand long term, but it would beat a New York winter by a long shot. And I was right.

I avoided the below freezing temperatures in New Zealand by traveling to Australia and heading up to Northern Australia (warmer in winter) during the southern hemisphere's coldest month of July.

Folks bundled up in Southern Australia in July

Identify Low vs. High Season

Travel seasons often correspond with weather patterns and national holidays happening in people's home countries and at the destinations. This means the volume of tourists increases during specific times of year.

Subsequently, countries will often raise prices to increase profits and reduce overcrowding. This means low season will get you the best prices and the greatest availability at hotels, on tours, and more.

Master Tip: There are some great little infographics out there describing each country or continent's low/high seasons. Alternatively, search "[country or city name] low season high season" to get an idea of the best times to visit.

I visited Thailand at the very beginning of their high season—October through April. October and November include the Loy Krathong and Yi Peng festivals, both of which I wanted to see. So I opted to go anyway.


I was lucky enough to get one-on-one SCUBA training despite visiting Thailand at the beginning of high season!


Cost was not really an issue for my trip to Thailand because it's so inexpensive there. I only ran the risk of being locked out of a room at some of the more popular hostels.

I found I was locked out of a room only on occasion because I would not book ahead of time. Even then, I was able to find another place with vacancies, sometimes right next door. If I had gone during the country's peak months during high season (December and January), I may not have had it so easy.

In Conclusion

Deciding where to travel is sometimes the most difficult part of planning a trip. Perhaps it's so difficult because first steps are always difficult.

But once you cover all the practical considerations, such as affordability, timing, distance, weather, and travel seasons, you can focus your attention inward.

Next time, I will discuss the most important parts of the decision making process: Listening to your heart, determining your comfort needs, and matching the destination to your goals and hobbies. Do the above and follow what I describe in the next post, and you won't regret your decision.