Taking your dream trip is one of the most exciting things you can do. Planning that trip, not so much.
Stressful and at times overwhelming, it can be a challenge to know where to start.
The good new: I’m going to take you through everything you need to know about planning your trip. From planning your route and itinerary to how to set a travel budget (it’s easier than you think), how to pick the right insurance, what to pack, what to do with your stuff while you’re gone and a bunch of other stuff besides, I’ll walk you through your trip planning on a step-by-step basis.
I’ve been travelling non-stop for over four-years and I face these same trip planning challenges each year. Sometimes I’m a planning genius, other times I’ve made some colossal screw-ups. It’s all culminated in a lot of know-how that I’m going to share in this series of articles, staring with how to plan your route.
How to Plan a Trip: Planning A Travel Itinerary
Note: Although I will focus on planning a longer, around the world style of trip, the points remain relevant for any itinerary that involves multiple destinations in one trip. I apply the formula below whether I’m planning a 12 months, 12 weeks or even 12 day trip.
1. Get your planning tools ready
Let’s pretend we’re baking a cake…or building a kit-car (if that’s more you’re thing). Before you get stuck in to making something, you gather your tools. When you sit down to start trip planning make sure you have the following to hand:
A good map
Even if you think you have good geographical awareness (and in my experience travellers are the worst people at assuming they are better at geography than they are), it really pays to have a map to hand when you’re planning your trip. It’s only in the detail of realising that Mexico City is actually pretty frickin’ far from Tulum…and that Belize is actually much closer, that you can plan a smart trip that will give you the most out of your time and money without zig-zagging across a continent because you’re pretty sure the border to Colombia meets with Bolivia somewhere (it doesn’t).
A word on maps: Everyone will have their own preference. After years of staring at maps, I find online and offline maps meet different needs.
At first, a good, large, printed world map is my favourite starting point because I can quickly and easily see locations and how they relate to each other without having to constantly zoom in and out of online version.
Google Maps helps me fill in the detail, but usually only after I’ve plotted my outline route. I also spent (read: wasted) a lot of time faffing around with markers on Google Maps, neatly plotting where I was going. As my itinerary changed, the process became a time-sucking chore. Don’t do it.
Map indulgence: If you’re prepared to pay for a map app, I’d highly recommend my all-time favourite, which is the map by National Geographic. Complete with a globe you can spin and (some) offline as well as online functionality, this is a very good-looking and fun to use world map app.
Alongside location, time is going to be the other biggest factor when planning your trip, so make sure you have a calendar to hand – ideally one you can jot notes onto. I’d suggest using a pencil and eraser for this activity, because things are going to change…often!
A pen and paper (or Word/Excel)
One of my biggest tips is to write everything down. Whether you’re a fan of spreadsheets, word documents or (like me), an old-school lover of pens and paper, find a system to record your thoughts and research. So many times I stumbled across a flight price, hotel I loved or handy booking site but didn’t make a note of it at the time. Unless you have a superbrain (sadly, not something I possess), you’ll probably spend hours a week later searching for the same info, which, as Sod’s Law dictates, will never be found again.
My handy Trip Planning sheet
I’ve produced an A4 sheet that accompanies this guide. You can find it here. It will help walk you though the planning process.
2. Start with your travel timeframe
The vast majority of people will have an end point to their trip. Whether it’s a two-week holiday or a global one-year adventure, the reality is that your travels will (probably) come to an end. Even for eternal wanderers like myself, there are dates such as Christmas and friends’ weddings that call me home, thus determining my trip length.
Unless you absolutely have to leave or return on a set date, the timeframe you will be working with might be a little fluid at first, until you get your flights (or other transport) dates fixed. My travel timeframe wandered by a couple of weeks in the early planning stages, but I knew I wanted to leave sometime mid-September, coming back a year later and worked with that.
Pro travel planning tip: If you can be flexible with your dates, that will help when it comes to finding cheaper airfares.
When you have your timeframe e.g. 20 September 2015 to 19 September 2016, convert it into days. For me, that was 365 days.
3. Make a travel wish list – all those places you want to go
Ignoring your timeframe for a minute, next comes the chance to daydream. Write a list of all those places you want to visit and the things you want to do on your dream trip. For now, I’d suggest dreaming big. There will be plenty of reality checks on your itinerary further down the line.
Not sure where to start? Think about:
- countries (or cities) to visit e.g. China, Rio de Janeiro, Italy
- sights to see e.g. Nazca Line (Peru), Petra (Jordan)
- events to attend e.g. Full Moon Party (Thailand), Day of the Dead (Mexico)
- activities to try e.g. meditation retreat (India), volcano boarding (Nicaragua)
- volunteering opportunities e.g. Orangutan sanctuary (Borneo)
- friends & family to visit e.g. Pedro (Barcelona)
3. Expect some FOMO* in your planning
*fear of missing out
The theory is that your wish-list will focus on a small number of places that represents the top-layer of dream destinations that you want to see. However, the reality of wanderlust is that you’ll probably create a much longer list that is a tangle of those destinations you really NEED (in the deepest hankering of you soul) to see and the places that, well, it would be a shame not to go to…because you’re taking an epic trip, you’re practically in the neighbourhood (next continent over) and John went there last year and it was A-MAZING.
Here’s how my initial round the world wish-list evolved…
Latin America: Peru (Inca Trail), Argentina, Brazil, Costa Rica, Mexico
Southeast Asia: Thailand, Indonesia, Laos
Middle East: Jordan, Israel, Egypt
On a one-year trip, it was pretty achievable, until my brain started to whirr at the potential –
- why not add in Australia…and New Zealand, because it is, after all, an around the world trip and who doesn’t go to Oz on a gap year?
- and I’ve always wanted to go to Hawaii, which I could “swing-by” on the way to Asia…
- …after I’ve visited Easter Island, which is part of Chile, so I should add Chile and Easer Island to the list too.
- And seeing as I’ll be paying for travel insurance for the USA (thanks, Hawaii), I may as well spend some time there – Route 66 sounds fun.
- Hmmm, and how do I get to Mexico from Brazil? I know, I’ll go overland, stopping at every Central American country on the way. Why not?
- I should also really revisit Vietnam and Cambodia too, given I’ll be so close in Asia and I loved them the first time I visited.
- Wow, such a fantastic adventure I’m planning…wouldn’t it be a shame to miss a whole substantive continent like Africa. Ok, I’ll add Africa…and Europe, because I could surely overland back to the UK from either Africa or the Middle East…
It’s amazing how many itineraries I see that seem to have gone through a similar thought process. But don’t kick yourself just yet if you’re in a similar position. You were trip dreaming …
….but now it’s time to wake-up.
4. Put some pins on a map
To see the full extend of your draft itinerary, the first step is to put some pins on a map, ideally a large wall map you can take a few steps back from (otherwise a few crosses on a smaller, printed map will do).
On a country by country basis, mark on your map every country you want to visit. Unless you’re super focused or have a good level of control over your wanderlust, your map is probably going to look a little out of control. Mine certainly did. I confess I had around 45 countries on my list by the time I’d finished my draft travel itinerary. Big dreams, sure, but realistic? Hell, no!
With your map looking busier than your local bar on a Saturday night, it’s sadly time to get real. Don’t worry, you’ll still end up with a fantastic itinerary. In fact, it will be even more fantastic because it will be achievable.
5. Check your travel speed: Countries divided by timeframe
Before you start randomly plucking pins off the map, this little test will probably be one of the biggest eye-openers of your travel itinerary planning. It’s far from scientific because you absolutely will not spend the same amount of time in each country (e.g. Brazil and Belgium merit very different visiting timescales based on country size alone). Nevertheless, to get a broad feel for the speed at which you would be travelling if you made it to all of the countries on your draft itinerary, divide the number of countries you have listed by the number of days you have available to travel.
Shocked? I was.
With around 45 countries on my wish-list, I divided this by my anticipated one-year of travel, and came up with the number 8. Yes, just 8 days per country. Realising that there were a minimum of three places I wanted to see in most countries, that number divides further to just over 2 days per place. And that wasn’t taking travel time and unexpected glitches into account.
Reality hit. It was time to go back to the drawing board.
On travel speed: it’s really difficult to say what a good speed of travel is because the answer depends on so many factors. Some people are confident they can consume a city in a day or two, others like to linger and blend with the locals. If it comes down to it, I’d rather see a place quickly opposed to not seeing it at all, though overall my preference is slower travel.
Obviously, the time you have available will be a huge factor – as will the land mass that you’re trying to cover and the speed and efficiency of the local transport system. Trying to “do” Germany in a couple of weeks might be more realistic than the same effort in Bolivia. And, how long you’re travelling for will also make a difference. You might want to rush around in the first months of a year-long trip, but keep that pace up and you’ll likely burn-out fast.
As an indication, on my first around the world trip, I probably moved to a new place on average every 4 to 5 days. Of course, some places I just stopped at overnight on the way to somewhere else and some places I stayed for a couple of weeks. However, at that pace, I got travel burn-out after 9 months and had to slow down. If I could do that trip again, I’d combine short stints of fast travel (moving every 4 to 6 day) followed by longer stops up to a month in one place. Ahhhh, hindsight how we love thee.
6. Re-drafting the draft: start with the anomalies
Returning to your map, have a good, hard stare to identify any obvious anomalies in your plans. Flights are going to be one of your biggest costs, particularly if you’re going around the world. Assuming you don’t have an unlimited budget (oh how nice that would be), then the fewer continents you visit, the cheaper your ticket. Equally, the more you can concentrate the countries/continents you visit, the better (financially and in terms of time).
So, if your itinerary involves mainly places in Asia, but you’ve added a quick “stop” in Africa to safari or you’ve included a few days in South America to walk the Inca Trail, these locations sit at odds with the rest of your itinerary and should come under serious scrutiny. I’m not suggesting you don’t go somewhere because it doesn’t fit in with the rest of your trip (I’ve done some illogical travel in my time because I REALLY wanted to visit a place). If you really feel the need to go and can afford it (financially and time wise), you can make it happen. But consider some alternatives first….
7. Carve out any places you can visit another time
There is a temptation when we plan a travel itinerary to plan it as though it will be the last trip we will ever take. Sure, this may end up being the biggest trip you take for a while, but that doesn’t mean you can’t do separate, dedicated trips to some of the places on your draft itinerary at another time.
Africa and Europe were the biggest blips on my itinerary – I was covering too many continents and I knew that I could happily craft a separate trip to explore Africa, while Europe is one of those places I could visit via weekend trips from the UK.
The result: I decided to focus on Latin America, Asia, and the Middle East…pretty much my initial plan before FOMO took over.
8. Make a Top-5 (or 10) list
Anyone who had opened the flood gates to trip dreaming knows that we can quickly lose sight of what initially motivated us to travel. However, its important to try and cast your mind back. Hiking to Macchu Pichu, the food in Mexico, walking on the Great Wall of China, seeing the Taj Mahal and the Orangutans in Borneo were probably the top five items that made me want to see the world. Sure, my dream list is way longer (and continues to grow), but if I were only able to do five things, it would be those five.
Being as strict as you can, look at your wish-list and identify the very top layer of what it is that you want to see and do on your trip. Don’t worry, the other places don’t need to be struck off just yet – some of them can be included if it makes sense. For example, adding Brazil to my trip wasn’t too big a deal given I planned to visit neighbouring Peru. But, for now, focus on your top choices.
This process might involve a lot of drafting and re-drafting.
9. Re-do your travel map and re-check your travel speed
With your pared down wish-list in place, return to your map – do the countries look achievable and logical? Have you excluded any places that make more sense to visit separately/on another trip? Also, don’t forget to sanity check your improved list by recalculating your travel speed.
Assuming everything looks good, it’s time to get down to some serious business – adding a timetable to you trip plans and looking for flight
10: It’s time to talk about timing: Break it into bite-size sectors
At this stage of your planning, you’ve probably just got a start and end date (which may or my not be entirely set) and a list of places you want to go. The next stage is breaking that down into a little more detail by sketching out some broad timescales for your trip.
Some people are more decisive than others when it comes to committing to a travel itinerary. I tend to sit on the noncommittal end of the spectrum enjoying far-off end dates with little planned in between. Other people prefer to have a much more regimented plan down to the time that they will brush their teeth on the 54th day of their trip.
The reality is that somewhere in-between these two extremes lies the ideal level of timetabling.
As a starting point, look at the continents you plan to visit and roughly divide your travel time between them.
For my trip, I wanted to spend broadly 6 months in Latin America (including South and Central) and another 6 months on the other side of the world including Southeast Asia, China, India and the Middle East.
Going one step further, I decided to split my time 4:2 months between South and Central America. For the remaining 6 months I opted for 3 months in Southeast Asia leaving a month in each of China, India and the Middle East. They were broad-brush numbers but, because my ticket involved a lot of overland travel, and because I bought a ticket that permitted free date changes, these broad plans were enough to start booking flights. But first, I did a few more checks.
11. Weatherproof your plans
If you travel around the world for a year, it’s unlikely you’ll be in every destination during high-season. Plus, you’re unlikely to want to be, because high-season is pricey and busy. However, there will probably be some destinations on your list that are more compelling to visit at a particular time of year.
Being eternally cold in the UK, I was wedded to the idea of spending a few months enjoying the peak sunshine in the Caribbean coast of Central America. Coconuts, hammocks and a barefoot lifestyle felt like a dream. In contrast, it didn’t matter much to me that I’d be visiting India during monsoon season because I was largely going there to eat the food and meditate – both of which were all-weather experiences. By flipping my itinerary to start in South rather than Central America, I was able to achieve my Caribbean dream. I got soaked in the monsoon-season in India as a result but I didn’t care.
Decide what is important to you weatherwise and make-sure your itinerary matches up.
12. Be festival and permit savvy
Weather isn’t the only seasonal matter to consider. Many festivals like Carnivale in Brazil and Songkran in Thailand come but once a year. There’s little point getting to Rio de Janeiro in January if your main reason for visiting is the festivities. Also, don’t forget about some of the more popular activities that need weeks if not months of planning in advance. England’s famous Glastonbury festival sells out in the year before the festival and there is fierce competition for tickets, along with some pretty intensive application requirements. Another continent over, walking the Inca Trail isn’t quite the stroll in the park you might think. You can only hike the trail with a permit and only so many permits are available each day, meaning tickets sell out well in advance. Oh, and don’t turn up in February when the entire trail is closed down to let it breathe for five minutes.
Write a list of all the festivals and activities you want to experience together with the dates and availability and make sure your timeframe is set around that. Of course, there might be some compromises you have to make. I arrived in Mexico too late to witness the Day of the Dead festivities and too early for Carnivale in Rio. It can suck, but it’s often a reality on an around the world trip.
13: Finding flights: One-way all the way or a round-the-world flight
There’s scope for an entire book on the topic of booking flights and maybe I’ll get around to writing one one day but in the meantime here are the main things to consider when trying to weigh up the benefits of taking an around the world ticket versus individual flights.
Advantages of one-way tickets
- one-way tickets provide the most flexibility in your itinerary allowing you to change course on a whim as well as backtrack (not allowed with most around the world tickets);
- it very easy and cheap to get around by land in most countries so if time is on your side and budget is an issue, you can save a lot by taking the slower, land-based route. However, check your facts first. In Europe it’s often cheaper to fly than take the trains and the USA doesn’t have the most extensive public transport system unless you’re hopping between major cities;
- consider whether you might be away for more than 12 months or might extend your stay. Many around the world tickets don’t allow travel beyond 12 months – I ended up going for a few more months than expected and had to sacrifice the final leg of my ticket;
- local airlines can work out cheaper once you’ve crossed big stretches of land or water. Consider combining a one-way tickets in and out of a continent with local flights or region passes (some continents like South America have region specific deals like the LAN Pass that offer better value airfare if booked with a return international flight). However, research individual flights in each continent you plan to visit. While Europe has a healthy, competitive market for low-cost airfares, South America really doesn’t (with the exception of Colombia).
- as an alternative to individual flights consider pre-booking a basic around the world fare which you supplement with overland travel or local flights;
Advantages of round-the-world tickets
- although it will depend on your country of residence and where you’re going, there are some excellent-value tickets out there that come in way-cheaper than separate flights when you’re travelling long distances;
- pre-booked flights are much better for budgeting – you don’t need to leave a chunk of money in your travel account to ensure you can get home, because that leg of your journey has already been paid for. They’re also better at avoiding bill-shock: you might find an excellent deal into Japan on a one-way ticket, but if you’ve found a fluke, cheap flight when all the outbound airfares are $500 or more, you may come to regret your one-way decision;
- consider your most-likely mode of travel. If you have a short timeframe, you’re probably going to need to fly a bit more, meaning a round-the-world ticket could help you see more and save at the same time;
- around the world tickets provide some structure to your plans and help you keep moving;
- many countries require proof of onward travel as part of their entry or visa requirements, which is easily managed with an around the world ticket (though you can just buy a single outbound ticket if you’re booking one-way tickets);
- you’re more likely to collect air miles – locking yourself in with one of the big alliances like One World or Star Alliance means you will accumulate air miles for future trips, which can be a bonus.
For my first around the world trip I opted for an all-inclusive ticket. It cost just under £3,000 (around $5,000) and was a good deal because it included Europe, South and Central America, a brief stop in the USA, Japan, Southeast Asia, China, India, the Middle East and then back to London. It also permitted me free date changes and very reasonably priced destination changes (within the same country).
Once I’d flown into the main hubs, I did most of my travel by bus, train or boat, occasionally supplemented with side-flights that I booked locally e.g. to Bali and Borneo.
Since my first trip, I tend to go one-way all the way, though this can have it’s problems (looking at you, Mr Philippines). In Europe, I suffer the low-cost airlines and haven’t yet seen a good enough cost reason to buy an Interail Pass.
A word on reverse trip planning: so far, I’ve been talking about writing a travel wish-list then looking for flights. However, don’t overlook the possibility of working the other way round. A few times I’ve found amazing flight deals and I’ve used those to determine my travel itinerary – that time I flew from Mexico and spent three months in Hawaii springs to mind.
Equally, there are numerous around the world ticket deals where the destinations and travel dates have already been selected. For a basic ticket you’re typically looking at something like Europe, New York, LA, Australia, Bangkok, Europe. If you’re on a tight budget, are pretty open about where you go and are feeling adventurous, why not let the ticket dictate your destinations?
14: Flights – BIY (Book It Yourself) or call in the experts?
When you’ve had a graze around the internet, checked out some sample flight prices and considered the local transport options (and costs) in the places you plan to visit, it’s time to get booking.
There are two main routes to take – BIY (book it yourself) or use a travel agent. I’ve tried both options over the years and as a general rule of thumb, my experience has taught me that for simple tickets, you can book it yourself. But for anything that doesn’t involve a straight return, includes open-jaw or is across more than one continent, you’re better calling in the experts.
My around the world ticket was reasonably complex because of the number of stops I had. I did spent (way too much) time trying to plot the trip myself using British Airways’ multi-route planner. I tried the same thing with Star Alliance and I even tracked down a Virgin Atlantic around the world fare. But the process drove me to madness, not least because most airlines won’t give you confirmed flight dates a year in advance.
Calling on the experts, I got an agent dedicated to helping me plan my trip and over the course of several conversations I got it booked.
I looked at around 5 or 6 different flight itineraries before I finally booked. A couple were too expensive (adding Easter Island to my ticket bumped the price up considerably). One itinerary saw me culling Hawaii because it mucked up the rest of my itinerary and I also played around with my Latin America route – swapping north to south to south to north.
The agent gave me excellent advice on which direction to travel (for weather and the best prices), which countries to add onto my ticket versus buying cheaper, local flights (Bali) and which options would seriously increase my ticket price. I doubt I would ever have gotten the same price as my travel agent did.
Of course, if you’re booking one-way or just spending time in one country or continent, it can be cheaper and easier to book yourself. Don’t discount the idea of an agent, though – get a quote from the professionals and check it against the prices you find online.
You might find this useful, my guide to 101 Tips for Cheap Flights.
Which agent to use?
I can’t comment on all of the ticket agents out there, but I have used three of the biggest. Here’s a quick summary of my experience.
I booked my first around the world ticket with this company and was thrilled with the planning and booking process. The ticket also included free date changes and a “Travel Butler” to aid me along the way (i.e. manage any changes). I would have wholeheartedly recommended the company except I had a major glitch mid-trip. Because the airlines won’t book dates so far in advance, the last part of my itinerary was only tentative. I hadn’t realised that, and it hadn’t been made clear to me. So, when I failed to email to confirm the dates about 6 months in, my ticket was forfeited and the agent tried to extract around £150 to reinstate it. It was a less than pleasant experience that involved some fraught phone calls and emails, some of which left me in tears. I haven’t looked at the company since, which is a shame since the initial experience had been great.
How can I sum up Trailfinders? A high-end experience that is probably going to cost you more than you’d pay elsewhere. I’ve travelled with Trailfinders to Egypt and I also asked them to quote for my trip to Japan and South East Asia. In both cases, the trip would have been cheaper elsewhere, but the experience was otherwise very pleasant.
My current reigning favourite travel booking company is STA travel. They consistently manage to beat the price of all other agents I’ve tried. The staff are friendly and, better still, are very creative with their flight suggestions. By tweaking the countries in SE Asia that I flew in and out of from Japan, they were able to shave hundreds off the price I’d been quoted elsewhere…and no, you don’t need to be a student or of student age to book with them.
15. Booking the main hub stops on your trip
Having got some price quotes, it’s time to book the backbone of your trip. Even if you’re going down the one-way ticket route, I’d still earmark some dates along your route to keep momentum going. When I took my second (nearly around the world) trip, I failed to do this, which got me stuck in Mexico for five months, lacking any real motivation to leave. That’s not such a bad thing if you have time on your hands, like I did, but if you’re taking a once in a lifetime trip, you want to make sure you see what you came to see.
At this stage you should have a decent list of where you are going, when and the hubs that you’ll hit to get there.
My itinerary looked a little like this:
Oct-Jan: South America
Feb & Mar: Central America
Apr – Jun: Southeast Asia
Sept: Middle East
My flights took me London-Quito(via Madrid)-overland to Rio de Janeiro-Panama-(overland to Mexico)-Singapore-(overland to Bangkok)-China-India-Jordan-London.
If you’re taking an overland trip, do the same when booking buses or trains.
I had a broad plan in place, and with the comfort of knowing I could change the dates along the way, I booked.
When it comes to booking, check out my list of over 100 top travel sites.
16. Don’t over-plan
I see so many itineraries that detail right down to the activities that must occur each day. However, the reality of long-term travel is that things rarely pan out like that. Let me give you an example…
Here’s the kind of detailed travel itinerary I’ve seen:
30 Sept: Fly London to Quito
1 Oct: Quito – sightsee city, language classes (PM)
2 Oct: Quito – chocolate tasting, trip to the Ecuator
3 Oct: Baños – white water rafting or horse riding or both
4 Oct: Mancora – learn to surf
5 Oct: Mancora – more surf lessons
6 Oct: Mancora – language classes and surf lessons
7 Oct: Cuenca – explore city
8 Oct: Cuenca – Panama hat factory/shopping
9 Oct: Lima – stock up for Inca Trail hike
10 Oct: Cusco – explore city
11-15 Oct: Macchu Pichu – hike Inca Trail
16 Oct: Cusco – visit orphanage
17 Oct: Fly Lima to Buenos Aires
Believe it or not, I’ve seen this style of itinerary run for an entire year-long trip. But here’s why it won’t work:
- first off, the itinerary has made no account for travel time. Most travel in South America takes the best part of a day or night and even in Europe a short jaunt can end up consuming half a day by the time you check out of your room, find the train station or get to the airport and get to your accommodation at the other end.
- there is no room in a detailed itinerary for things not going to plan – weather, travel disruptions, losing your passport, acquiring a killer hangover..ahem, getting sick – they can all slow you down.
- there’s no space for spontaneity – what if you meet a super cool bunch of people you want to hang out with but you can’t because your itinerary is all tied up for the next six months
- long term travel is a marathon, not a sprint. You need to build downtime into your trip or you’ll get serious burn-out that will either make you want to go home, or stop you in your tracks for at least a couple of weeks.
- if you travel too fast, you’ll go home with little more than postcard pictures for memories.
With the exception of drawing out some rough plans e.g. the places you want to visit in Peru, booking your first few nights’ accommodation and visas (more on that soon), I’d really recommend keeping your travel itinerary as fluid as you can.
With your flight dates to guide you (or self-imposed “I must leave Chile before Christmas” kind of promises) and hard dates fixed in (Inca Trail or carnival), let the rest flow and I promise your trip will be all the better for it.
Are you planning a trip at the moment? Let me know if you have any questions. If you’ve planned a trip and have any other suggestions to add, please feel free to mention them in the comments below.
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