travel planning

Planning the Perfect Vacation Trip Itinerary

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.

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.

Get your planning tools ready

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).

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!

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.

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. Read more tips at

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.

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.

Was I really going to race through the entirety of Mexico in just over a week? What about Japan, and surely Brazil could merit months? Reality hit. It was time to go back to the drawing board. This article has more on this topic.

Make a Top 5 or Top 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.

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.

Flights – 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.

Please follow and like us: