Last updated: 7/17/2023 | July 17, 2023
Planning a trip can be stressful.
Where do you start?
What is the first step? What’s the second step? Is everything okay? Is there a better path to take? How do you know what to do? What do you book first?
There’s a lot to think about, especially if you’re going on a really long trip.
Taking a vacation and traveling the world is a huge life change, and it’s easy to feel overwhelmed. Multi-month trips don’t just happen. There is a lot of planning needed to make your dream come true.
And this endless list can feel overwhelming at times.
So how do you stop feeling overwhelmed?
It’s not as hard as you think – and I’ve developed a unique four-step process to help (patent pending):
First, buy your plane ticket to where you want to go first. (Not sure where you want to start? Simple. Start where airfare is cheaper.) All you need is the first flight.
Second, turn off your computer and stop visiting the 93,754,302,948,320 travel websites (except mine – you should ALWAYS read my site!). You’ll suffer from too much information if you don’t.
Third, go out with your friends and celebrate the start date of your trip.
There – that’s it. You have bought your plane ticket. are you go. There is no turning back. You don’t have to worry anymore. All other planning is secondary.
I once heard at an industry event that people would check out up to 20 locations over the course of 40 hours where they were planning a two-week vacation. This is madness. You don’t need to do that much research.
No wonder I get so many emails from people saying “Matt, I feel like I’m in my head.”
Information is power, but in our information-overloaded society, too much information leaves us conflicted and helpless.
I understand that you may feel a lot of anxiety when planning your trip because you want to make sure that everything goes smoothly. I remember what it was like when I was planning my first trip. I had every guide under the sun in my room. I have created spreadsheets. I searched everything. I had several tracks laid. I have lists upon lists. I was always worried about the “perfect flight”.
I have been there but I can tell you from years of experience that the more you plan your trip, the more anxiety you will face. You will overwhelm yourself with so much information that you will do nothing but click through it.
Planning gives you a sense of ownership for your trip. There is fun in that. It is one of the best parts of traveling.
but Over planning It will lead to stress and I can tell you that once you hit the road all your plans will change anyway.
Someone will tell you about a new destination and you will race there instead of going to Amsterdam.
You will wander the streets and into unexpected restaurants.
You will meet a group of people who will convince you to stay on that tropical island with them for a little while longer.
All you should have when you leave is a general idea of the direction you want to go and a plan for your first few stops. Then, let the wind take you.
(This rule applies even if you’re taking a short trip. Come up with a few things you want to see each day and then let the rest of the day fill itself out. Go with the flow!)
In 2006, my first itinerary through Europe was supposed to look like this:
Oslo -> Prague -> Milan -> Florence -> Rome -> Naples -> Corfu -> Metorea -> Athens -> Greek Islands -> Athens
But it ended like this:
Oslo -> Prague -> Milan -> Florence -> Rome -> Venice -> Vienna -> Amsterdam -> Costa del Sol -> Barcelona -> Amsterdam -> Athens
Almost nothing has worked out as I had planned. I passed better. Cooler, more interesting things and people pulled me in a different direction.
A recent trip to Southeast Asia was completely changed when a friend said “Would you like to come meet me in Chiang Mai?”
Instead of flying to Bangkok, I ended up in Chiang Mai and then on to Laos!
I rarely kept my original plans. I don’t know many travelers who have it.
After you book your flight, make a list of everything you need to do before you fly (it won’t be as long as you think):
That’s the biggest part of it – and most of these things can be done a few months before you’re gone.
Go to the bottom of your list.
Buy a book or two to get some general knowledge on how to travel and prepare for your trip.
Read a guidebook and get a good idea of where you are going.
Make a general plan and then fill in the details along the way.
Everything will work out by itself.
And when that happens, you will wonder why you stressed so much in the beginning.
Book your flight: logistics tips and tricks
Book your flight
Find a cheap flight with Skyscanner. It’s my favorite search engine because it searches websites and airlines around the world so you’ll always know that no stone is left unturned.
Reserve your accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it constantly shows the cheapest rates for guesthouses and hotels.
Don’t forget travel insurance
Travel insurance will protect you from illness, injury, theft and cancellation. It is comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
Want to travel for free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodations – all without any additional spending. Check out my guide to choosing the right card, current favorites to get started, and see the latest best deals.
Ready to book your flight?
Check out my resources page for the best companies to use when traveling. I list everything I use when I travel. It’s the best in class and you can’t go wrong with it on your trip.