The Art of Planning An Overseas Trip

The Art Of Planning An Overseas Trip

How do you travel? With a lot of planning, or just go with the flow and deal with each step along the way? I suppose each of us has a different take on the best way to travel, and will likely end up somewhere in the middle of the two extremes.

When I look back at the trips that I have taken, I very much land in the category of liking to have everything planned. I am happy to have a little bit not entirely planned. At the same time, I love the idea of leaving the house knowing what flights to catch, where I will be sleeping. Just not having to guess what is going to happen.

In reality, planning can make the trip go a lot smoother. But there is also the aspect that it can very much leave you drained before even starting on the journey. However, on the flip side that effort up front can make for a much easier and more stress-free trip once you leave home. So today I want to look at some of the options using a couple of my trips as an example.

Planning The Unplanned

At heart, I am a planner. However, I still find that it is possible for me to approach a trip which includes some part that is unplanned. So far that is something that I have only been able to do successfully once, and it was on my first overseas trip.

On my first overseas trip, I had a five day period in England. I did book a rental car and a hotel for the first night, however, the rest was not booked. Of course, I was a little nervous about this. However, I did not approach the situation blind.

Even though I had four nights that I had no hotel booked, I did do my research before leaving home. Since I had a car getting around was easy enough. The research told me that I could easily book Travelodge hotels, which were scatted all over England, for the following night. Each night I would arrive at the hotel, find a place for dinner, and check out my options for the next day, and book the next nights accommodation.

Planning On The Road

It may be the short time that I tend to stay in one place when I travel or a side effect of my liking to have everything planned in advance. But I have faced a huge challenge in planning future parts of the trip while I am on the road.

Obviously, the example I gave above in England, shows that it is possible. However, when faced with organising multiple things together, such as hotels and flights, while only having a short period in one place I find that it feels like I am wasting time which could be used exploring where I am right now.

My second trip overseas was where this become a highlight for me. I had around eight weeks in total, and when I left home, I had hotels and flight booked for the first two weeks, followed by a four-week cruise. There was still two weeks after the cruise which I still needed to book before leaving. However, although I had planned to get this sorted before leaving on the cruise, the reality is I was too caught up in seeing and doing, and I end up with three days in San Diego booked after the cruise returned.

I learned a great lesson in this process. Do not rely on having internet access on a cruise ship to plan hotels or flights. I arrived back to San Diego after the cruise with three nights accommodation booked in a hotel there. I had no idea where I would head to after that, though. In the end, after spending the better part of a day trawling the internet. I organised flights and accommodation in Dallas, San Francisco, and Los Angeles. However, the hotel choices were not entirely the most convenient. Likely I would have made different choices with more time to research.

In the end, it all worked out, but this lesson came at a price. I paid more to visit these places than if I had booked the same before leaving on the cruise. Also, I did not have any motivation behind the places I visited, and as such doubt, I gained as much from visiting these places, as if I had some idea why I wanted to visit.

A Planning Disaster

My first overseas trip was a near perfect plan, while my second trip was 75% there. However, you would have thought that I would have learnt my lesson on leaving the planning to the last minute. Unfortunately, that seems to be a lesson that for me was achieved the hard way.

My third trip overseas consisted mainly of a 26-day cruise. There were around three weeks between arriving in Los Angles and departing on the cruise from Vancouver. A week before my flight to Los Angeles I had two nights book in Las Vegas, and nothing else.

Although everything worked out in the end, it was for me far too stressful and draining booking so much in the last week before leaving. Although in this case, I did get to book places I wanted to visit, I believe I did likely spend more than I needed on the accommodation and flights. The stress of this spilt over into the trip itself for the first few days, but soon enough I enjoyed the trip.

Planning success

It was finally on my last major overseas trip which I took in 2012, where the lessons from my planning problems, successes, and disasters finally came together for total success.

I was not leaving anything to chance on this trip; It was my longest trip overseas to date, and I had grand plans to see a lot of places. As I left home to commence this journey I had all but four nights and two flights booked. Including, bookings for 40 nights in hotel rooms, a 29-day cruise, five nights with a friend, and 16 flights. The four nights and two flights were but just awaiting confirmation from a friend.

The planning success of this trip is not something that happened by accident. I knew after the last minute bookings of the last two trips; something needed to change. So it was a matter of putting in the time to make a process that would work for me.

Steps To Successfully Planning A Holiday

In the end, there were no great changes to how I researched where I wanted to travel. But I changed the process and tools for planning and tracking what was getting booked. The biggest problem I faced was with so much research; I easily lost track of what bookings were made and what still needed booking, and which was the option I was planning to take.

To help all this along, I did three things.

  1. I created deadlines for the booking and planning stage
  2. A spreadsheet I created to track the prices and alternatives
  3. I created a document which only included my booked and confirmed travel details


There were only two goals that I discovered that were important to me, that I identified would resolve the majority of issues I had previously experienced. Primarily looking to avoid last minute bookings and over paying for something I did not want to do.

  1. Investigate both aspects of travel before booking anything, e.g., research hotels and flights to be sure a cheap flight did not result in overpaying for the hotel.
  2. Book everything at least one month before the travel or stay date.


A new aspect of my planning process for this trip was a spreadsheet where I would track my research for each stage of the journey. Helping me in four ways.

  1. It helped to see the dates for travel and hotel visits easily
  2. I could easily record which airline flight, and hotels were my top choice in a destination
  3. It helped me to track my costs for the trip
  4. I also kept a column for identifying if I had booked or needed to book this stage.

Here is a small Screenshot of part of the spreadsheet.

The Art Of Planning An Overseas Trip

I set the spreadsheet up with the first column identifying, either where I was travelling from and to, or where I would be staying. The following columns were the dates for each item, either a travel date or check-in and check-out dates for the hotels. I included prices, and whether it was in Australian or other currencies. A column that identified if I had booked (green) or needed to book (yellow). Finally, a column that gives me the name of the hotel or airline I was considering.


I had taken a similar approach to this document on my first trip, however, over the next two trips, this seemed to slip away. I brought it back for this journey, and while it did replicate the spreadsheet to some degree, it also included extra details.

The document was a running list of exactly what was on which day, flight details, departure times, arrival times, booking references and other details related to the booking. I would only add an item to this document when it was booked and confirmed.

The Art Of Planning An Overseas Trip

Throughout the trip, I would check this document, each day and highlight the day. It turned out a great way to chec and confirm the plans for each day.


It is the combination of the goals and these two tools I created. All of this helped me to come out of this trip feeling that it had been a planning success. The spreadsheet made it much easier at the investigation stage of planning. Instead of pieces of paper everywhere with different hotels and flights. I would just make a couple of copies of the spreadsheet to try alternatives. Using one master copy to add my final decisions too.

Get Planning

If you are someone that loves to plan things, that planning a trip is a great test of your ability to plan. The planning for any future trips that I take is going to be much easier. Primarily so that I can enjoy the journey, stress in advance is better than stress on the journey.

How do you go about planning your trips? Why not let me know in the comments below. You can connect with me on social media, pick your favourite social network below.

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