How to Plan Your Trip Abroad

I am a notorious, non-planner. I book a flight and show up somewhere, knowing that I have time to develop an understanding of a place because of my “travel deeper” mentality. However, I realize that not everyone has a few months to spend in one location, and for that, you need to plan your trip!

Hopefully this trip planning guide will help you go through the process of planning that life-changing trip abroad!

5 Steps to Plan Your Trip Abroad

How to Plan Your Trip AbroadThese are the five important trip questions that you should ask yourself before your next adventure:


It sounds silly, but this can be a difficult decision. Where do I go? First of all, let’s remember that this is a good problem to have. The freedom to choose your destination is awesome!

There are four factors that go into choosing a destination for me:

  1. Time Frame – How much time do you have for your trip? If it’s only one week, and you live in New York, you probably won’t be flying to Australia or China. If it’s a longer-term trip, you might want to think about going someplace further from home to maximize the flight cost and distance.
  2. Budget – How much money do you have to spend? As I mention in the video, Bolivia is cheaper than Brazil, Albania is cheaper than Italy, etc… People often think that they need a ton of money to travel the world, but that’s just not true. I actually spend more money when I’m home than when I’m on the road (rent, bills, car payment, and all that good stuff).
  3. Inspiration – Where have you always dreamed of? Is there an Instagram photo or YouTube video that you fell in love with? Is there a language that you’ve always wanted to learn or perhaps a food you’ve never tried? Make a list.
  4. Visa Requirements – How easy is it for you to get into the country and stay (legally)? Many countries offer 90-day tourist visas, while others require a strict process. For an American Citizen, this is the website to find out the Visa Requirements for each country –

Plan Your Trip - Google Flights


The biggest cost for most international trips is actually getting there. If you can find a good deal, it changes your entire travel budget. Here’s a few ways to find the best possible price when you plan your trip:

  1. Go Incognito – It has been said that airline websites and comparison sites can track your flight searches based on your cookies/cache and manipulate prices around that information. I search flights using an Incognito window in my web browser just based on habit, but there isn’t too much information to confirm this assumption.
  2. Book Midweek – Another interesting belief is that airlines change their flight rates on Tuesday at 3pm, while others believe Wednesday at midnight is best. Either way, I try to look at flights a few different days before I book.
  3. Fly Midweek – This is one is definitely true, and pretty simple. Fly when less people want to fly, i.e. midweek.
  4. 6-8 Weeks Out – Don’t book too early, and don’t wait until the last minute. If you can book flights around six weeks out, you should be in good shape.
  5. Individual Tickets – Sometimes on long-haul flights it’s cheaper to book individual leg tickets. For example, If you’re flying from New York to Sydney, it could be cheaper to book individual tickets through Los Angeles. This might also give you an opportunity to spend a few hours/days in a new location.
  6. Student Rates – If you’re a student (under the age of 26), there are some good deals out there to be had. Check out STA Travel or Flight Centre for more information.
  7. Travel Credit Cards – When you plan your trip, consider one of the few good credit card programs out there for travelers. I use the Chase Sapphire Preferred Card and the Chase Southwest Airlines Credit Card. Check out The Points Guy website for more info on this.
  8. Flight Alerts – Many travel websites allow you to set alerts for particular flights and destinations via email. These are great if you have a lot of time before your trip. Check out Airfare Watchdog for this.

Plan Your Trip - Finding Cheap FlightsWEBSITES FOR CHEAP FLIGHTS:

These are the comparison websites that I look at when booking a flight. I also visit airline websites directly if I see that they have many flights and/or good prices for a destination.

ThriftyNomads ► Booking Cheapest Flight Possible Anywhere
xpatmatt ► How to Find Cheaper Airline Plane Tickets Online
US News ► 8 Insider Secrets to Booking Cheap Airfare

Skiing the French Alps
Views from my room at the Club Med Val Thorens


Where you stay when you are traveling is completely dependent on what type of traveler you are. Are you a road warrior, backpacker, cultural vulture, budget-relaxer, or luxury seeker? If you’re the last one, call me. Otherwise, here are a few different options for accommodations when you plan your trip…

+ – Good for budget-conscious travelers, still looking for the traditional vacation experience.
+ Hostel World – For backpackers and super-budget travelers (great for solo travelers).
+ AirBnB – For those looking for a local feel, or simple need more space than a hotel can accommodate (great for groups).
+ Couchsurfing – Meet and interact with people from all over the world, even if it’s just a cup of coffee.
+ Woofing – A different style of accommodation where you live and learn on an organic farm.

Nepal Earthquake Relief


This is more important for solo travelers like myself, but making local connections before you arrive is a major advantage. Nowadays, thanks to social media, it is easier than ever to connect with people around the world.

So when you plan your trip, simply go on your favorite social media platform and search for people that you want to connect with. Maybe it’s someone on Instagram, Snapchat or YouTube. It doesn’t hurt to just ask them for advice or if they’d like to meet up. Couchsurfing and Matador’s new app Travelstoke are great travel-focused social media platforms.

If you need help finding people to connect with, don’t hesitate to contact me vial email.

Amazon Rainforest Tour


After your destination is chosen, flights are books, and accommodations are confirmed, now it’s time to think about the other stuff to plan your trip. This includes travel insurance, language learning, and daily planning.

Allianz Travel Insurance
World Nomads

+ Duolingo FREE app
+ Follow Benny Lewis

As I mention in the How to Plan Your Trip Video, after all this is done, I start making a list of all the things I want to see, do and try at the destination.

That’s it, if you follow these five steps you should be able to plan your trip abroad no problem. If you have any other specific questions, please don’t hesitate to ask.

My name is Gareth Leonard, a Marketing Director turned World Traveler with a passion for slow, meaningful travel. I have been traveling the world full-time for the past 9+ years and document it all on Instagram and YouTube. Come join me!


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