Last Updated: 7/17/23 | July 17th, 2023
Planning a trip can be stressful.
What’s step one? What’s step two? Will everything work out OK? Is there a best route to take? How figure out what to do? What do you book first?
There’s a lot to think about, especially if you’re going for a really long trip.
Taking time off and traveling around the world is a big life change, and it’s easy to feel overwhelmed. Multi-month trips don’t just happen. There’s a lot of planning that is needed to make your dream a reality.
And that endless list to do can feel overwhelming sometimes.
So how do you manage to 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 the airfare is the cheapest.) All you need is the first flight.
Second, turn off the computer and stop visiting 93,754,302,948,320 websites about travel (except for mine — you should always read mine!). You’ll suffer from information overload if you don’t.
Third, go out with your friends and celebrate the start date of your trip.
There – that’s it. You bought your plane ticket. You’re going. There’s no turning back. There’s no need to worry anymore. All other planning is secondary.
I once heard at an industry event that people will look at up to 20 websites over the course of 40 hours as they plan a two week vacation. That’s insane. 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 over my head.”
Information is power, but in our information-overload society, too much information leave us conflicted and powerless.
I understand you might be feeling a lot of anxiety planning your trip since you want to make sure everything goes right. I remember what it was like when I was planning my first trip. I had every guidebook under the sun in my room. I created spreadsheets. I researched everything. I had multiple itineraries drawn up. I had lists upon lists. I was constantly worried about having “the perfect trip.”
I’ve 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’re going to overwhelm yourself with so much information that you’re going to do nothing but stress over it.
Planning gives you a sense of ownership over your trip. There’s joy in that. It’s one of the best parts about travel.
But overplanning 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’ll race off there instead of going to Amsterdam.
You’ll wander the streets and into unexpected restaurants.
You’ll meet a group of people who will convince you to stay on that tropical island with them just a little longer.
All you should have when you leave is a general idea of what direction you want to go and plan your first few stops. After that, just let the wind take you.
(This rule applies even if you are just are taking a short trip. Come up with a few things you want to see each day and then just let the rest of the day fill itself in. 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 up like this:
Oslo –> Prague –> Milan –> Florence –> Rome –> Venice –> Vienna –> Amsterdam –> Costa del Sol -> Barcelona -> Amsterdam –> Athens
Almost nothing worked out as I had planned. It worked out 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 “Want to come meet me in Chiang Mai?”
I have rarely ever kept my original plans. I don’t know many travelers who have.
After you’ve booked your flight, come up with a list of everything you need to do before you go (it won’t be as long as you think):
That’s the bulk of it — and most of this stuff can be done a few months before you go.
Go down your list.
Read a guidebook and get a good idea about where you’re going.
Develop a general plan and then fill in the details along the way.
Everything will work itself out.
And, when it does, you’ll wonder why you stressed so much in the beginning.
Book Your Trip: Logistical Tips and Tricks
Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s 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 accommodation — all without any extra spending. Check out my guide to picking the right card and my current favorites to get started and see the latest best deals.
Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.