Planning a Trip – Start from the Beginning

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Like many things in life, planning a trip can be overwhelming.  Where do you start?  How do you know where to go?  My goal with this post is to give you some structure to thinking about your travel. 

Step 1:  Identify your anchor!

This is the first step for any traveler.  Some do this intuitively and for some it will take a little reflection.  It will also be a little different for every trip….

An anchor is the most important objective or guiding factor.  An anchor can be incredibly specific or very general.  The anchor can be a specific location or activity, it can be specific dates, it can be a budget, or it can be a vague notion of just wanting to get away.  It can be a feeling – what do you need or want from this trip?  Here are a few examples:

  • I want to visit my parents over the holidays. (very specific)
  • I want to go somewhere with my parents this next year. (more general)
  • I want to take a family trip over Spring break. (specific timing but flexible location) 
  • I want to take a family trip somewhere warm over Spring break. (more specific)
  • I want to go somewhere this weekend that is less than 3 hours away.
  • I have two weeks of paid time off in the fall and I want to go to Peru.    
  • I want to go to lie on a beach in February. 
  • I want to go to Europe for two weeks. 
  • I want to go to Guinea Bissau during the turtle season and then see other things in the area while there.  (This was my last big trip)
  • I want to go to the Caucuses in the fall.  I have two weeks to explore.  (This is my next big trip)
  • I saw a sale on a flight to the US Virgin Islands and jumped on it.  (This trip is next week from the time of writing this post)
Photo courtesy of Spokenlight photography

Step 2:  Identify, and if possible, prioritize, other important considerations.  Thinking through your additional priorities will help settle on a location and dates and help scope your planning as you make reservations.  Below are some examples:

  • A new location or somewhere you have been?
  • Is the purpose of the trip to relax and probably spend a lot of time in the hotel or accommodations or will you be out and about most of the day?
  • Do you have a budget?
  • Do you want luxury?
  • If traveling with a family (or other group) do you need a single room, multiple rooms, multiple bathrooms, or something with a common area? 
  • Is there something specific that you want to do or see and need to plan your dates around? 
  • How far (or long) are you willing to travel?  Do you want to travel by a particular mode of transportation?  If flying by air, do you want non-stop, no more than 1 stop? 
  • How long is the trip?
  • Do you want to plan a day or either end (or both) to get ready and then unwind? 

Step 3: Like building a puzzle, start with the corners.  Based on your answers in steps 1 and 2, you should now have an idea about what is important – dates, location, budget … Make one reservation to build the trip around.  Here are some examples:

  • If the dates (but not the location) are your anchor, then start with google flights (or another favorite platform) and search from your home airport to “anywhere”, a country or continent. 
  • If you have a destination in mind but are flexible on the dates, then use a search engine with your origin airport and destination but you can scan prices for specific dates and seasons.  Skyscanner has a flexible date option.
  • If looking at a specific hotel or activity, then start with that availability.  For my recent trip to West Africa, I wanted to visit Organo National Park and see the turtles.  I started with making reservations there and then built the entire trip around those dates. 

Step 4:  Map out the outlines of your trip.  This will help you figure out what arrangements and logistics are required.   I like to create an excel spreadsheet but a word document or the back of a napkin will work too. 

  • Do you want the trip to center on a single destination or do you want to move around?
  • If moving around, do you want to rent a car, take the train, fly?
  • What are the other “big” things that you want to do and where might you need reservations?
  • Are you taking any day trips?

Step 5:  Go through the trip and then start again.  I start with flights and hotels.  I then go back to day 1 and figure out tours or events that need advance reservations.  I then go back to day 1 yet again to fill in other activities, places to eat, and back up plans. It may feel repetitive to go through your plans multiple times but it will often save you time in the end and help refine your plans. As an example, if you plan day 1 start to finish and then move on to day 2, you may realize you might need to leave very early in the morning which then could require rework for day 1….

Start with the big things: Hotel, Transportation, Important activities

Then look at other plans, activities and tours

Then fill in the blanks!

Other Thoughts –

Steps 1 and 2 will be easier if you keep some sort of running list of places that you want to go.  It will be no surprise that I have a very complicated spreadsheet but a simple list in your phone works too.  I am open to new places, but I know where I want to go in the fall if I have a long weekend, a week, or two weeks.  Some of these are more expensive than others, some I want to do alone, with a particular person or with a group of friends. 

By having clear priorities in steps 1 and 2 it can also help with budget creep, and you will only pay for what is important.  If you have identified that you want to relax and have lots of down time, then maybe you pay for a room with a view and a place with amenities.  If you will spend all of your time out exploring, then keep it simple.  If I am traveling for a week or less, I keep all of my flights to one stop.    There is no one right answer.  But by thinking through what you want it can help simplify the process and create a trip that is right for you! 

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