“If you fail to plan, you plan to fail,” so they say and after years of travel, we have some tried and true methods when it comes to designing our adventures for smooth sailing. Like most people, we have constraints, especially time and money. Affordable group tours are usually not an option and frankly, we like to do some off-the-beaten-path kinda stuff that isn’t commonly included in mainstream itineraries. Therefore we have taken international travel planning into our own hands and personalise itineraries according to our unique criteria.
Here is a short guide to how we select a destination from our ENORMOUS bucket list, followed by how to go about trip planning for the most unique, relaxed and trouble-free travel experience possible. I’ve even included a free, printable travel planner with prompts and checklists that you can download at the end of this post.
1. Finding inspiration
Firstly we decide on a destination, a high priority selection from our bucket list is generally the seed for each trip. We are currently eyeing off Hawaii! I also find the visual nature of Instagram and Pinterest makes them fun platforms for seeking inspiration and tools for researching destinations and experiences.
2. Geography and timing
If we are dancing around multiple ideas, we start to narrow it down by proximity and time. For example, seasonal experiences such as cherry blossoms in Japan or swimming with whale sharks in Mexico require certain timing. Furthermore, as ex-pats, we try to wisely use our current location as a base to explore the surrounding region while we are geographically in short reach.
3. Generate a “must-see” list
Destinations that are high on our priority list are usually justified by a certain experience or experiences we’d like to have in those places. This forms the basis of our “must-see list.” From there we research additional things to do and see in and around that location. There are plenty of “top things to do in…” lists around the internet ready to be Googled (and on this blog).
4. Budgeting time and money
Next, we look at what is achievable in our timeframe and budget. To determine this we find group tour itineraries online that cover the bulk of our “must-see” list at the kind of comfort level we like to travel, which gives us an indication of the time and money required. For instance, when planning our trip to Hawaii we might look at Intrepid Travel and see what a 10 day, “Comfort” style group tour costs per person and what they include in their itinerary, to determine what’s realistic within our timing and budget. This is a great travel planning hack that saves a tonne of time!!
5. To plan or not to plan, that is the question
When planning international travel, the next step is to decide whether we feel comfortable designing the trip for ourselves or if we need an expert collaborator.
The determining factors have been most commonly language, development and safety. As monolingual English speakers, we call in help for many non-English speaking destinations. We also get help for developing countries, those that present challenging political situations or might offer experiences that cannot be simply booked online or over the phone etc. Examples of places we have enlisted professional travel agents/tour companies to assist us in our international travel planning include Cuba, Galapagos Islands and Myanmar. This leads into our next question…
6. How do you like your travel?
From here it goes 3 ways, we’ll call them: Complete DIY, Partial DIY, or Expert Level
Complete DIY – On our trip to the Yucatan Peninsula, Mexico we decided it was safe and navigable enough even on our limited Spanish to go it alone. We booked flights, accommodation and hire car online; created a rough itinerary; mapped it out and away we went.
Partial DIY – On a Partial DIY such as our trip to Mexico City and Oaxaca, we would generally book our own flights and accommodation, then book day tours for certain activities that require transport. For the rest, we explore freestyle based on our research and the plethora of free self-guided walking tours available around the internet and in guidebooks.
Expert Level – Sometimes we don’t have time to plan an extended trip with complicated connections. Imagine this – you’ve just spent 4 days driving across remote parts of the Bolivian Altiplano, and it is time to cross the border into Chile. You drive up to a shack in the middle of nowhere that marks the border checkpoint. There is nothing for hundreds of miles in this beautiful but cold, barren mountain landscape at over 4500m above sea level. Your Bolivian tour company can take you no further and so you are at the mercy of your Chilean tour company to pick you up. You don’t want to get this kind of connection wrong folks–best to get a tour company like the wonderful Contours who coordinated our month-long, five-country South American odyssey.
In cases like this, we research local tour companies and provide them with as much information as possible, including our must-see list, hotel standard preferences, timeframe and budget, and let them do the heavy lifting. We are by no means passive in the planning process, we still do our research so we can provide the agent with plenty of direction. Though we are also open to their suggestions and guidance.
NOTE: Generally we always book our own flights to/from our starting/ending point, no matter which of the three ways we go. You don’t want travel agent mark-ups eating into your budget and it’s so easy to book directly with most airlines online.
7. Selecting a tour operator or travel agent
If you choose to go with “Expert Level” you’ll need to hire an agent to help you through the rest of the international travel planning process. We rarely use the same travel service twice. This is because we select local operators who are specialists in their destination. We prefer to support local businesses for several reasons:
- Firstly, their intimate knowledge of their homeland can really benefit us in finding unique experiences. For instance, in Hue, Vietnam our tour guide (booked by a local operator) arranged us a special meal in a female Buddhist monastery because his sister was a nun there. This is the kind of cool experience you can have with a company that lives and breathes their home/your destination.
- Secondly, it is more likely our money will go back into the local economy, which is important to us as we endeavour to travel sustainably.
- Thirdly, we avoid large markups that foreign agents add to bookings.
8. Getting down to the nitty-gritty
At this point, we’ll start getting right down into the logistics of international travel planning. Things like visas, airport transfers, security, currency and language. I’ve created a detailed international travel checklist of the things we research about our destination as part of our travel plan and why.
Knowing these things pre-departure saves a lot of time and stress when we get to our destination. Though it may seem a little tiresome at times to do all this research, I’ve never regretted it. In fact, I’ve had moments during trips where I’ve thought “thank goodness we sorted this out beforehand because I’m too tired/hungry/uncomfortable/late” to be faffing about and figuring it out on the fly.
9. Be prepared to throw it all away
Ok, maybe not all of it – that’s a tad dramatic, but no matter how much you decide to plan ahead remember to remain flexible. Uncontrollable factors like weather and public transport change things on the fly and you may need to adapt. Plus, you’ll discover new things along the way that you’ll really want to do/see/eat, so you need a little wiggle room in your itinerary.
It’s common for us to divert from our itinerary just from sheer exhaustion because we plan to squeeze a lot into the little time we have and sometimes it’s just way too much. For example, the last night of our Jamaica road trip, we had planned to go out on a boat trip at Glistening Waters and experience the bioluminescence, but we were too tired. We had dinner and went to bed early instead, so we were fresh for the last day’s activities. Sometimes you have to prioritise and take a break so you can enjoy the rest of the trip – another reason to have a flexible travel plan.
Download my free international travel planner here:
I hope this insight into how we go about travel planning is useful and you are able to design an overseas trip to suit your needs, with minimal hiccups and maximum fun. If you have any questions, please feel free to drop them in the comments below.
Peace, love & inspiring travel,
Madam ZoZo

