Vacation Planning 101

How do you plan your vacations? Do you obsess over every last detail? Do you plan down to the minute? Or do you prefer to simply book a flight and wing the rest of your time?

I love to plan. I’m pretty sure part of the reason I love to travel is so I get to plan something. There is something quite satisfying about taking a broad question, “Where should we go on our next vacation?”, and turning that into a detailed itinerary. Can you see my OCD tendencies coming through yet?

This post is about the process I take when planning any type of travel. As a software developer, I essentially use the same process for solving any large and complex problem. I take my initial big question, “Where should we go on our next vacation?”, and break it down into smaller manageable tasks. Once one task is completed I can then iterate of the process by breaking down the remaining work into smaller tasks until they all get completed.

Naturally, the first step in answering the big question is deciding where you want to go. No other tasks can be completed until this gets done. To determine an appropriate destination you must ask yourself what the goal of the desired vacation is. 

Are you visiting family? 

Do you want to escape the cold? 

Are you looking for adventure or relaxing? 

Who will you be travelling with?

What is my budget?

I think you get the picture. Once these questions are answered you can start narrowing down the types of places you could possibly visit. I started planning my next vacation about 10 months in advance. I knew I would be travelling in August, with my wife and two kids and was looking for adventure. Early on I thought about going on a three week road trip looking for some adventure. This started out with an elaborate plan to drive to Canada’s east coast all the way to Newfoundland. While this certainly would have been an epic adventure after some initial research and reading related travel blogs I decided such a trip would involve too much driving and not enough adventure.

I restarted the process again with a revised set of goals. 

The next destination I set my sights on was a road trip to West Virginia. This is another location that has plenty of adventure but required less driving. This time around I got much further in my planning. Using a combination of Google Maps, travel blogs and tourism websites I was able to come up with a three week loop with stops in key areas along the way.

This brings me to my next point. Areas or zones. Once I’ve answered the big question and have a destination in mind I break the work down further by coming up with a list of broad areas or zones that look like they would be worth visiting. A zone could be a city or a geographic area that I am interested in exploring. I find having these areas defined makes it much easier to plan a route as well as understanding how many areas can feasibly be visited. Depending on the location it may make more sense to find a home base to make day trips to each area instead of packing up and traveling to each area.

Determining the areas to visit goes back to the original questions on why a specific location was chosen. With the broad location already known it becomes a lot easier to discover the areas that will provide the desired activities and exploration. For this process I rely heavily on existing travel blogs from past travellers as well as Tripadvisor reviews and forums.

Now we are getting to the fun part. It is time to start booking. This usually happens 4-6 months out. For accommodations I generally book a combination of mid-range hotels and AirBnb's. On longer trips AirBnb is great since it provides an opportunity to do some laundry and make our own meals. Hotels are also great for the additional services they provide like on on site bar/restaurant and pools (important with kids!). 

There is still plenty of work to be done such as planning driving routes, renting a car and booking activities but those will be saved for a future post.

Also, stay tuned to see my planning steps in action as I embark on an epic six-week adventure with my family in August.  We will be visiting three very different locations in three very different countries.