Putting Pencil to Paper: How to Start Planning Your Trip

Adventure is a State of Mind

‘Tis the Season

For many people, the period from early spring through early summer is prime trip-planning season because they are planning trips for later in the summer. If your travel adventure is fairly simple – you’re traveling domestically to an area that is not too crowded in the summer, or you’re traveling abroad but with only a couple of people involved and a fairly basic itinerary – this is the perfect time to plan a summer travel adventure.

On the other hand, if you’re traveling to someplace where it may be difficult to find an available place to stay or you’re traveling with a large group that can make accommodations and travel reservations more complex or limited, you may want to start your planning as early as a year in advance. That means if you’re planning to travel abroad next summer, you’re also starting your planning about now, too.

Personally, I love to travel almost anytime of the year, which means that for me, planning season is all year long!

Getting Started

Once you’ve made a decision as to where you’re going, it’s time to get started with planning. We’ve looked at how to get started in general, but let’s take a more detailed look at how to start planning your travel adventure.

Paper and Pencil

Okay, you don’t literally have to use a pencil, or even paper, but you need someplace to write down the rough ideas of what you’re wanting to do. I personally use pen and paper to write out preliminary plans and activities, putting each activity on a separate line. I also include a line for each travel day – for example, in planning a trip to Greece, one line might read “fly to Athens.” If we’re going to take a ferry to Crete, I’ll write that down on a separate line as well. At the very beginning of the process, each day is just labeled “Day 1,” “Day 2,” and so on.

I usually write in travel days first. Then I start adding activities that we want to occur at certain points in our trip, such as the day after we arrive or on the one day that activity is available. If I know we want to visit the Acropolis, for example, I’ll write that down. If we have a specific restaurant we want to visit, I’ll write that down. On the other hand, if I know we want to go to a nice restaurant one evening but have no clue what restaurant that is, I’ll write down “visit nice restaurant in Crete.”

At this point, my travel companions and I will be throwing out ideas, sometimes in a single evening over glasses of wine, and sometimes over the course of days or weeks. This is also the time that we look at the guidebooks and do internet searches for things like “Top Ten Things to Do in Crete.”

Edit and Order the List

If the list ends up having hundreds of items, obviously you need to eliminate some things… unless you plan to move to the area. Talk with your travel companions about their and your priorities.

You can also start to group things by looking at a map and starting to figure out how different places fit together. For example, if in Crete you want to visit both the Samaria Gorge and the Cave of Diktaion Andron – the mythical birthplace of the Greek God, Zeus – a quick glance at the map shows that they are much too far apart to attempt to visit them in the same day. (You can use Google maps to figure out how long it takes to get between locations by foot, car, or public transportation.)

On the other hand, if you pick a restaurant you want to visit and it’s a five-minute walk from a beach you also want to visit, you might easily combine them into a single day’s (or even afternoon’s) activities. It’s fairly common that places you want to visit will cluster together on the map, or one location will be right on the route to the other location, so those can be grouped together on the same day.

“Would you tell me, please, which way I ought to go from here?”
“That depends a good deal on where you want to get to,” said the Cat.
“I don’t much care where–” said Alice.
“Then it doesn’t matter which way you go,” said the Cat.
“–so long as I get SOMEWHERE,” Alice added as an explanation.
“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”

Lewis Carroll, Alice in Wonderland

Get a Calendar

I know I’m sounding pretty old fashioned with the pen and paper thing, and I’m going to sound even more antiquated when I admit that for the next step, I use a paper calendar. Gasp! I know many people (including myself) increasingly rely on their electronic calendars, but at this stage in the planning, I like to be able to visualize the entire time I’ll be gone, not just a single day at a time.

Many of us receive paper calendars in the mail because of donating money to a charity. If you get those, they’re perfect and don’t cost you any money… aside from the donation, of course. Sometimes businesses, like insurance agents, give them out for free.

If you don’t receive any free calendars, you can print off a free copy of just the months you need. Do an internet search for “free calendar template” and you’ll find lots of options.

Check the Dates

I use the calendar to visualize the dates we have available and the activities we hope to be able to do. If I know of any set dates or limits, I mark those first. For example, if we want to go in May but have to be back by a certain date in order to attend a reunion, I’ll mark that on the calendar. If there are holidays in the country we are visiting, I’ll mark those as a reminder to do our research as to whether museums and restaurants tend to be open or closed on those days.

The next step is to consider whether any of the activities on our wish list are limited to certain days of the week, in general. For example, if a museum we want to visit is closed on Mondays, I’ll mark something like “no museum” on the calendar so we keep that in mind while we’re figuring out what we want to do and when we want to do it. It’s painful to take a trip, leaving one day in your itinerary to go to a museum or historical site you really want to see, only to realize that it’s closed on that date!

Not every date on the calendar has to be planned… unless, of course, that’s your preference. Personally, I’ll have a few things planned when reservations are needed ahead of time or it’s something, like a local farmer’s market, that is only open one day a week. I like to leave some days, or at least half days, open so that we can be a little spontaneous in what we choose to do. I do, however, have a list of activities that we hope to do in an area so we have a general idea of how much time we need to spend in that location.

On the calendar, the days without something specifically planned for that day will be marked with the general location, such as “Athens” or “Crete.” Then I look at the unscheduled things we’re hoping to do and see in that area and make sure that we have enough overall days to fit those things in, even though I’m not specifying which day is specifically for which activity.

Assess for Flexibility

At this point, I have a rough itinerary and rough travel dates. Now is the time I assess whether there is any flexibility in the dates by checking my calendar and talking to my travel companions. If there isn’t any flexibility, then we know our dates are set and we can start doing things that lock us in, such as buying plane tickets (if needed) and making reservations for where we are going to stay.

If there is some flexibility, then I’ll keep that in mind when making flight reservations. Being open to options, both in terms of times and locations, can definitely help you to find affordable flights. There have been times when flipping the cities we plan to fly into and out of has saved us a significant amount of money, and we just reversed our plans regarding the order of the places we wanted to visit.

The Basic Structure

At this point, if you follow a planning strategy similar to what I’ve described, you have your dates, your travel reservations, and at least some of your lodging and/or activities reserved. That’s the basic structure of your travel adventure.

Depending on how free and spontaneous you want to be during your travels, you might now consider yourself done with the planning… except for packing, of course!. If you prefer more structure, however, you can continue to make decisions about your plans and fill in more details of the itinerary.

Either way – spontaneous or planned – you’re well on your way to creating your own unique travel adventure!

Have you planned a travel adventure before? Or, have you let others, such as a tour company, do the planning for you? If you have experience with travel planning, do you have a system or strategy for organizing the process? Feel free to share any of your ideas in the comments section below.