Adventure is calling! … But where should you go? How do you get there? And what do you need to do before you can turn your dream into a reality? That’s where we come in! We’ve currently traveled to 34 countries across 4 continents (with hopefully more coming soon) and know a thing or two about how to plan a trip.
As serial over-analyzers and lovers of the ‘Plan to Plan‘ method – we will walk you through exactly how to plan your own trip, take stress out of the equation and give you our insider tips so you don’t miss a beat.
When planning a trip, we find that breaking the process up into ‘Phases‘ works best. We feel less overwhelmed when steps are broken into more manageable pieces and this guide will explain how we plan our trips in detail.
Are you ready to begin planning your perfect adventure? Let’s get stuck in!
This is us being perfectly depicted on ‘The Emotional Overload’ rollercoaster. We’re clearly at different stages of the planning process!
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Break Up Planning a Trip Into 3 Manageable Phases
We are all different. Genetics, personality traits, habits and attitudes make us all unique.
But although we are all unique, common patterns emerge among us.
- Aside from the super organized, most long term travelers tend to book the first week or month in detail and then once comfortable with the whole idea of backpacker life, plan just a few days in advance. Because who knows what might come up?!
- Those taking shorter trips – such as a 2 week vacation – tend to plan almost all specific details in advance. Who wants to lose valuable time planning what to do that day with just 2 weeks away from work?
It’s always fun meeting people from all over the world and getting to know how they work or function when traveling. Our analytical minds love to run social experiments. We are scientists by trade and now we have a travel blog … this is our bread and butter!
Some love to plan (like us – at times!) and some hate to plan (like us – the rest of the time!).
Planning a trip in advance can be as conflicting as the angel on one shoulder and the devil on the other. Sometimes it pays off and other times it doesn’t.
No matter how you prefer to travel or how long you intend to travel, the planning process can always be broken down into 3 manageable phases to make life easier and less like your brain might explode.
Start by breaking your plan into these 3 phases, then set achievable steps and goals within each phase. All you need to do next is watch your dream trip create itself before your eyes. No stress, just positive reinforcement!
Phase 1 – Research & Determine (5 W’s and the H)
Follow each step within the first phase to formulate your ideas and turn them into an actionable plan. Each of these steps will affect the others and at times you will need backtrack but don’t let that demoralize you. It happens to everyone!
Our advice is to be honest about what you think is achievable.
For instance, don’t try to plan a year traveling around Europe and North America if your budget is US$ 10,000. We’re sorry to break it to you, but that just isn’t feasible!
Step 1 – How Much Time Will You Spend Traveling?
The first part of this whole planning a trip process begins with determining how much time you have on your side.
Time is the one thing we wish we had more of but can do nothing about!
- Can you squeeze 2 weeks vacation time out of your job for a dream holiday to Italy or French Polynesia?
- Are you able to take a 3 month sabbatical to backpack South East Asia?
- Or maybe you’ve been thinking about quitting your job to travel without an end date in mind?
Whichever category you fall into, the first thing you have to establish is the duration of your proposed adventure. How long you can travel will determine all other aspects of planning.
Step 2 – When Do You Want To Leave?
Are you planning a trip way in advance? Or are you last minute planning? The subsequent steps will change focus depending on the answer to those questions.
For those last minute planning a spontaneous trip, you will need to double down and get to work! However, if you’re planning a summer vacation that’s 6 months out, you can relax and take each step slowly. People work better in their own ways.
For instance, Kristen works best when planning early and taking things at a gentle pace, whereas Mark works best under pressure with the clock ticking. This system is perfect for us!
Working out when you can feasibly leave on your adventure gives you the framework to set small and achievable goals.
If you’re planning to quit your job in 6 months and travel the world for a year, now is the time to get stuck into planning. A year is a long time and the world is a big place. If you leave a trip like this until the last minute, you could risk missing out on once in a lifetime opportunities.
Remind yourself of the 7 P’s of planning. Piss Poor Planning Promotes Piss Poor Performance.
Step 3 – Who Will You Travel With?
It’s highly likely many of you will already know who you will travel with even before beginning to plan a trip. Maybe you’re going on a family holiday or a romantic couples weekend getaway?
For those who are undecided between solo travel or traveling with a friend, now is the time to have those discussions.
We always travel as a couple which makes Step 3 obsolete for us.
Our travels have allowed us to meet hundreds of others traveling both solo and in groups or couples. There are pro’s and con’s to all types of travel, just like most things in life!
Step 4 – What Shape Are Your Finances In?
Working out available finances is arguably the most important aspect of planning a trip, whether you are leaving tomorrow or in a year.
When we begin to plan a trip, we flip back and forward between steps 4 and 5 like a yo-yo.
Can we afford to go to X? Yes. What about Y? No. Ok, back to step 4 – where can we afford?
Unfortunately, it is money that makes the world go around and without much of it, you will be limited to where you can go and what you can do.
That’s not to say you can’t see a lot of the world without a ton of money. There are some super savvy travelers among us who can travel for months on a shoestring budget. However, not everyone is ready to Couchsurf and hitchhike.
Be very careful not to get carried away when planning a trip. Consider your budget (or projected budget when you will leave) and plan only for that amount of money.
If you are planning a short vacation you will have much more control over finances. You know you’re going to get paid again soon so a splurge isn’t out of the question! In contrast, long term travelers will constantly be checking their finances; once they leave for their trip and that number will decrease every single day until the end.
Step 5 – Where Do You Want To Go?
When you have a firm concept of how long you want to travel, when you can leave, who you will travel with and your estimated budget – it’s time to get to the most exciting part of all: creating a travel itinerary.
A question we often get asked is, “how do you know where you want to go?”
We do something our ancestors have been doing for over 2000 years: Look at a map!
Seriously, buy a huge map and stick it on your wall. Study each continent and begin to formulate a route. Indicate places you would love to visit using pins or colored sticky notes.
Once you have a shortlist of dream destinations, fire up google maps and prepare to lose yourself for hours! This is Mark’s bread and butter. Mark looking at maps is like a pig rolling in mud.
If you’re not as interested in maps (that’s totally fine, not many people are!), here are some alternative ways to find travel inspiration:
- Read our travel blog! And read other blogs too! There are hundreds of fantastic first hand resources on the internet written by people who love travel and want to help others to do the same. We always read a handful of blogs by people we trust to give honest opinions.
- Change up your google searches to ‘the best place to travel in X year’ or ‘the most obscure travel destinations’. Be creative!
- Pick up some Lonely Planet books.
- Look for specific events, festivals or concerts around the world
Step 6 – Why Is It So Hard To Save?!
You’ve meticulously cultivated the trip of a lifetime, now you just need to do one small thing. Finance this trip!
Whether you are going on a one week trekking holiday, a 1 month live aboard scuba diving course or road tripping the states – you will need to save up enough money to pay for the pleasure.
You have already worked out your budget in step 4. So you have the goal in front of you. Is your departure date 3 months away? 6 months? Maybe a year?
However far ahead you plan to leave, you will need to put some kind of savings process in place.
Saving for vacations or long term travel is HARD. Your excitement is at fever pitch but time seems to stop. Days at work start to drag more and more the closer you get to the big day.
The key is can be found in one simple word: Discipline.
It’s easy to start well with the best intentions but it’s equally just as easy to lose focus. Put yourself on a strict saving regime.
Make judgement calls on every single expenditure – is it want or need? Do you want that thing or do you genuinely need it?
If it’s a want, don’t spend the money, save it. Be disciplined.
Once your bank account begins to swell, fight the temptation to ‘treat yourself’. If you think that you won’t be tempted, think again! That 80″ TV you wanted is only US$ 1,000 and you now have 10 of those saved for your trip – can you get by on US$ 9,000?
No! You can’t! Put the TV back! Be disciplined.
Phase 1 Planning a Trip Complete!
Awesome! You are officially one third of the way towards stepping foot out of the door.
There are more challenges to come but you’ve smashed the hardest part out of the park! Now you can relax, even take a few days off planning your trip and come back fresh.
Narrowing down where to visit and coming up with an itinerary is by far the most difficult part for us because we both have FOMO (fear of missing out) syndrome.
With the whole world as an option, deciding where to go and where not to go is overwhelming! We just take it one step at a time, systematically including and discounting places until we agree on a winner.
The key is not to be disheartened when you think you’ve cracked it but for some reason it just doesn’t work out. Go back to the drawing board and start again fresh!
Phase 2 – Commit & Book (Take Action)
We can all daydream about vacations or backpacking the world for a year. But until you bite the bullet, until you commit by clicking the’ purchase flight’ button, a dream is all it will be. Once you have taken that giant leap mentally and it becomes tangible … “Oh crap! Guess I’m going now!”
How many times have you planned a route mentally and thought about how amazing it would be … only to snap back to reality in the office? We used to do it constantly! It’s about being brave and courageous. Take the plunge by purchasing at least your first flight. It’s an amazing feeling and there is no turning back!
Planning a trip gets easier with experience, you learn what works and what doesn’t. However, the one thing we can’t seem to get right is how much of the trip to book in advance. It’s a lose lose!
Plan ahead and lose flexibility – what if you love a place and want to stay but can’t? Plan nothing and spend all of your time in a place booking the next place!!
Some people like to plan the entire thing down to the ground, even dinner reservations. We met travelers with binders full of confirmation documents and they had no stress at all during their trip. Then there are those who prefer to book one flight and decide everything on the fly.
There is no ‘one size fits all’ best practice here. It all depends on your preferred travel style. That being said, we have learned over time, it really pays to be a little bit organized when it comes to your bucket list.
Step 7 – Book Your Flight To Seal The Deal
Now the real work can begin. We always use Skyscanner to book our flights. They offer the simplest user interface and consistently lowest prices. Our favorite aspect of Skyscanner is the ability to search for flights by month.
Let’s say you were flying JFK to London, instead of selecting the exact date (+/- 3 days which is what most websites offer) you can select by May, or by October. A flight calendar will show the prices of flights on every day that month.
Our number one tip for booking flights is to be flexible. It pays to research, search regularly and build up patterns of prices. Put flight alerts on specific flights of interest to you.
If you see a flight you want and it’s cheap, book it!
Don’t wait for it drop by US$ 5 because you’ll find it will go up by US$ 50 instead. Know the right time to pull the trigger.
Prices fluctuate many times a day. Don’t put too much emphasis on booking international flights on a Tuesday or domestic flights on a Sunday. Keep an eye on prices 6 months in advance, 3 months in advance, 1 month in advance and last minute. Research latest information online about patterns.
Clear your cache and cookies, even log on using another IP address to see if prices change. Flight booking search engines are built on algorithms like everything else online. Don’t try to outsmart them, just try to work them to your advantage.
A good rule of thumb is to book all of your major international long haul flights before you leave. That way you know your budget and can protect yourself from a monster flight price to get home from the other side of the world!
Step 8 – Book Ground Transport
This step is completely open to interpretation and dependent on where in the world you are traveling.
For instance, if you are interrailing Europe, you won’t need to book any transportation because you have an unlimited train ticket. But if you’re country hopping in Asia, you’ll probably be taking trains or buses between cities and airports.
The easiest way to break it down is by continent and best way to travel:
- Europe – Cheap budget flights with Ryanair, EasyJet, Jet2 etc between countries / Trains within countries.
- SE Asia – Cheap flights with Jetstar, VietJet, AirAsia, Scoot, LionAir, TigerAir etc between countries / Trains & Buses within countries.
- South America – Flights hit and miss for price. We found Chile and Peru had cheaper flights than Argentina. Best way to get around is by Bus. Be warned, some of them are LONG! We took a 24 hour bus from Bariloche to El Chalten, Argentina.
- North America – Road trip is the only way! Buy a cheap second hand car/Hire a car. Trains and planes too expensive. Traveling by bus is an option but not a great one.
Another example we have here: Let’s say you’re traveling Europe but not interrailing – booking trains in advance WILL save you money. This is the time to be organized. Booking buses and trains in Asia or South America will not save much (or anything) so there’s no need to be uber organized here.
Step 9 – Book Accommodation
Booking accommodation can be extremely rewarding and extremely frustrating. There are a limited amount of flights you can choose between, right? It’s the opposite for accommodation – there are SO many options for where you will sleep at night.
If you let it, this process will overwhelm you within minutes. How do you choose between 1000 hotels? When do you stop searching for an even better deal? Again, discipline is the key!
Something we find fascinating when we meet travelers on the road is the diversity of platforms everyone uses to book accommodation. Some swear by Airbnb, others use Agoda or Hostelworld and a high proportion use Booking.com. We fall into the latter.
We have been using Booking.com for years and still to this day we are staggered by how many hotel owners pull faces at us or make comments like ‘wow, you guys must have that booking genius thing – this is the lowest price I’ve seen’.
That’s not to say Booking.com has the best prices period. We sometimes ask hotels for a price directly and if it’s more than what we can see on our Booking.com app, we simply book it at the check in desk!
Play with filters, change from sort by ‘featured’ to ‘user rating’ for example.
Is it better to book hotels in advance?
If you’re on a tight budget, it might be worth turning up to negotiate a better deal. But for those with comfortable budgets, the difference in cost is usually minimal and the convenience of having it all booked in advance is worth it 10x over.
Just be aware of creating an itinerary so rigid that you leave no room for bad weather or delayed flights.
Step 10 – Create a ‘Major Activities & Tours You Can’t Miss’ Spreadsheet
This might seem a little overkill but trust us, it isn’t. You have a route planned through a country but what good is it if you miss some of the best things on offer in that country?
Life is about learning from mistakes and this is one mistake we won’t make again:
We visited Interlaken / Grindelwald, Switzerland and hadn’t researched things to do before hand. We were in a ‘winging it’ phase.
So, we went out for an expensive meal (everything is expensive in Switzerland – it was only a McDonald’s – just kidding!) and didn’t even know about the Jungfrau rack railway line through the Eiger to ‘the top of Europe’ at 3,454m. Once we discovered it, we couldn’t afford it.
We didn’t know about it, spent our money on other things and then couldn’t do it.
Plan major activities ahead. Make a spreadsheet or a checklist, even book some ahead of time if you have to or prefer to plan your whole trip in advance.
The more planning you do in advance, the less you will miss on the road.
Examples of times you have no choice but to plan way ahead are the W trek in Torres del Paine, Chile and Yosemite National Park, California. If you do not plan ahead here, you will most likely miss out.
If you’re not the type who plans things in advance, you may be forced into learning new skills!
Phase 2 Planning a Trip Complete!
Great job! You’re almost over the hill and it’s plain sailing from here. The difficult tasks have a big tick next to them, how awesome is that feeling?!
Now all that’s left is preparing for the amazing adventure that awaits you!
Booking flights, transport, hotels and activities is part of the fun and adventure. Try to enjoy the process! If you feel overwhelmed at any point, step away for a few hours or days. That is a tried and tested winner.
Always remember you can book hotels anywhere at any time – you don’t have to book your whole trip before you leave.
If there’s one particular leg of your journey you can’t quite make transport work or there are no cheap hotels available – go back a few steps and alter your route accordingly. These steps are all interchangeable!
We know it can be infuriating to have a route perfected, only for something not to work and find yourself back at the drawing board.
But consider this – would you rather be at home with this problem? Or in a foreign city with no idea where to go next, how to get there or where to sleep that night?
Phase 3 – Prepare & Pack (Departure Ready)
You’re on the home stretch, there are just a few important admin tasks to complete before you can finally say you are ready to leave on your trip. Get stuck into these last few steps as soon as possible, get ticks in the boxes and put your feet up with a cup of tea!
Phase 3 is about giving yourself the best return on your expenses. You could switch off once you’ve secured flights and accommodation but you’re shooting yourself in the foot if you don’t keep the ball rolling into the final phase!
Step 11 – Credit Cards
You might be from a country where paying with debit/credit card is the norm. Heck, you probably even pay for things with your phone these days!
However, when you travel through a region like Asia or South America, you won’t always be able to pay for goods and services with your cards. Cash is often king in developing countries or countries with few tourists.
For instance, we spent a month traveling Vietnam and can count on 1 hand the amount of times we paid for anything using a credit card.
This is what you need to do before you leave your home country:
1 – Sign up for a No Foreign Transaction Fee card for ATM withdrawals. On longer trips you will be taking money out of ATM’s regularly. Local ATM withdrawals usually offer better exchange rates than airport exchanges etc. If you use your home debit account, you can kiss goodbye to your travel budget. The local bank will charge you and your bank at home will charge you, double whammy. Not fun. Get this card sorted. Only use this card for withdrawing money, nothing else.
2 – Get yourself an awesome Travel Rewards Credit Card for all purchases. This is a no brainer, research (thoroughly) the best travel rewards card before you leave on your trip. The US has some incredible travel cards, compared to the UK for example. Look for the special points and bonuses for spending X amount of money in X amount of time. Choose the card that offers the best perks for your lifestyle. Always use this card for purchases and only purchases.
Step 12 – Call Each Bank You Have Accounts With!
It’s amazing the amount of trouble you can find yourself in over ‘I forgot to tell the bank I was going to spending money in Laos, Cambodia and Thailand’. They are doing it for your protection but when you can’t pay for anything or withdraw money, that doesn’t help you.
Let’s assume you have a Bank of America checking account, a Capital One Venture travel rewards card and a Chase Sapphire no foreign transaction fees card – tell every one of those banks what your rough travel plans are.
It doesn’t hurt to keep them updated either. We will contact our banks each time we move to a new continent and give them a rough plan of countries plus duration. They respond to your organization by offering perks. We had one bank give us a direct contact number in case we had any issues. We typically make our travel updates directly in the banks app so it really is an easy process!
Remember the 7 P’s of planning!
Step 13 – Get Travel Insurance
We’re not going to tell you about any gruesome tales here, we’re simply going to say it is not worth the risk to travel without insurance. You may be debating running the risk because insurance can be expensive.
That’s not the best idea! Especially those who are backpacking for longer periods.
Knock on wood, nothing serious has happened to us yet. No lost backpacks, no serious injuries, no muggings. But that could change at any moment, wrong place wrong time.
Peace of mind is worth more than the cost of travel insurance.
Could you imagine the cost involved in being repatriated to America with a serious illness or injury sustained on the other side of the planet? No insurance would be a killer blow.
Think about this – you’ve just bought a brand new Sony A7R IV mirrorless camera for US$ 3,000 and you lose it or have it stolen on your first day traveling. You don’t have insurance. Imagine the pain!
We use and highly recommend World Nomads Travel Insurance.
The company was created by travelers for travelers and you can see the quality immediately. There are other insurance companies so do your research but we think you’ll settle on World Nomads!
Step 14 – Check For Any Last Minute Bargains
This is where we hope you don’t spot an amazing last minute deal that’s US$ 100 cheaper than what you booked back in Phase 2 … !
It’s always worth keeping an eye on prices, even for things you already booked that may include free cancellations or changes to the booking.
In the days leading up to your departure, check prices on flights, trains, hotels and tours that you are interested in taking. There are always flash sales on things, it’s a case of being fortunate enough to stumble across them at the right time!
Remember, the time between when you started planning your trip to the moment just before you leave – high season might have moved into shoulder season or low season in a place you want to go. This means prices will be different and hopefully cheaper!
Step 15 – Pack Your Bags It’s Time To Leave!
Planning a trip is complete! All you need to do now is pick the perfect backpack and fill it.
We won’t go into detail here because you can read our huge Ultimate Long Term Travel Packing List guide for all the details on packing!
Be sure to pack according to where you’re going. If there are varying climates on your itinerary, pack for warm and cold weather conditions, even if that means taking a bigger backpack.
Pack carefully, make sure every single item is fit for multi-purpose use. Do not pack fancy shirts and jeans if you will only use them 1 time, you will end up throwing them out half way through!
We all have our own dress styles and preferences but our best advice for packing is to take plenty of comfortable gear.
Phase 3 Planning a Trip Complete!
And that is planning a trip made easy! Follow our stress free steps in 3 manageable phases and you’ll be out of the door in no time! See, that wasn’t so bad, was it?!
You’ve ridden ‘The Emotional Overload‘ and arrived at the end: Your plans are finally ready.
The most successful planners are the ones who can accept when they need to take a few steps back in order to take many steps forward.
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