Planning Our Big Trip

streets of Paris
Wandering the Streets of Paris

Many people have been surprised at our plan to travel around the world for the first six months of our early/active retirement. We are a little surprised too because it wasn’t anything we discussed until last summer. Our original plan was to go live in Europe for a year or two after we sold our house, which we will still be doing after Our Big Trip (OBT).

Our Plans

During OBT, we are planning to write blog articles on the places we visit so everyone can keep track of us. But a number of people have commented on the fact that it must have been a lot of work to plan such a trip. It was time consuming but certainly not impossible for anyone who is determined. This article is about the planning and I hope it helps you plan wonderful adventures for yourselves.

I have planned many trips over the years and I always start with a spreadsheet which has the dates and places laid out. Then I fill in the activities, hotels, and transportation. I did the same thing for OBT, but first, you will need to do enough research to figure out where you want to go.

Doing Your Research

The key to planning any trip is to do your research. Here is a list of ways to research places:

  • Do online searches for places.
  • Read blogs that describe sample itineraries.
  • Look at Trip Advisor’s list of things to do in the places that you are interested in visiting.
  • Look at the tours that are offered in a given place. I find Viator to be very useful for this.

Planning Your Own Trip

1. List the places you are interested in seeing.
In our case, we decided to start our adventure in Australia and we knew we were heading west, so I started by looking at Google maps.

2. List all of the places to see in the locations you are visiting.
If you are visiting New York, make a list of all of the attractions you want to see and make a note of any days they are closed. For example:

Trip Planning Example 1

Getting a Guide

3. Determine which places you feel comfortable traveling to by yourself and which places you feel you need a guide.
While I have been to many places on business, including China and India, I wasn’t comfortable traveling in Southeast Asia or India on my own. But in Australia and Japan, I felt I could navigate on my own, with the understanding that navigating a place on my own makes me somewhat responsible for everyone’s happiness. I decided I couldn’t lead the entire trip; too much responsibility for such a long trip. But I can certainly be the leader for a few weeks at a time.

4. Decide how active or restful you want your trip to be.
When we were still working in our corporate jobs, we often went on three types of vacations:

  • Sightseeing – fairly active
  • Beach – restful
  • Skiing – very active

Creating a Trip Worksheet

Regardless of whether your travel calendar is for a week or a month, the layout is the same. For shorter trips, I always had Morning, Afternoon, and Evening activities. That way, you can make sure you fit in all of the museums and activities feasible in a given location. Here is an example:

Trip Planning Example 2

If you are traveling with kids, make sure you plan enough downtime as you add the activities to your calendar. Cranky kids make everyone cranky. In addition, be sure to leave time for meals, kids need to be well fed if you want them to keep going.

Cost of Your Trip

Decide what you want to spend on your trip. Always start with the most expensive items such as transportation including airfare, trains, car rental, tolls and gas. Then decide how much you can afford for accommodations. 

Finally, record the pricing for all of the activities you are interested in. I never really include the cost of food because I figure we would have to eat even if we stayed home. When we stay at timeshares, we always make a grocery store run when we arrive, usually before we even check-in. Once you have some preliminary pricing, you can adjust your specific selections to stay within a budget.

When our kids were little we were pretty strapped for money, but we still went on vacation because we planned ahead. You can watch for deals on airfare and hotels if you already know you want to visit a particular place and you have a plan.

As you can see, I don’t always lay out my spreadsheet the same way. But when you find a layout you like, you can reuse it for subsequent trips.

Planning Our Big Trip

For OBT, we decided to anchor our trip with five main tours, where most everything is already arranged. In between the tours, we are either doing a beach week (or 2) or relaxing with sightseeing on our own.

Our tours are:

  • Southeast Asia
  • India/Nepal
  • Middle East
  • Southern Africa
  • Peru (I only booked a tour because I was tired of planning)

The trip plan for this trip is obviously much more complex than the other examples I have shown. Also, I did include the pricing on my copy, but I’m not showing it in the following example.

OBT Plan

I hope you have gotten an idea about how to plan your own trips and you feel empowered to try planning a trip on your own.

Where are you going next?

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1 comment

  1. We also do spreadsheets very similar to yours. Very helpful before, during, and after to keep things straight all in one place! Great for pics that have a date, but forget where we were when the pic was taken, etc. This post is filled with great information!

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