So, where are you going next? (How to Choose Your Next Travel Destination)

Having travelled somewhere every month for the past decade or so, this is by far, the most popular question I am asked. People are always very surprised when I reply with, “I don’t know yet” with only a week or two left before the next month, and are even more astonished when they realize that I’m not stressed or worried about it. Indecisive? Procrastinator? Hardly. I simply don’t need as much time to decide, plan, and prepare as I used to. Here’s how to choose your next travel destination:

  1. Brainstorm. Start gathering your destination ideas. Look for inspiration from magazines, websites, word of mouth…or perhaps you have a “bucket list” which includes some dream vacations. I keep an ongoing mental list that I add to all the time. Don’t worry about time, money, or any other constraints. At this point, your list doesn’t need to be logical or realistic, you are simply gathering ideas. Allow yourself to dream…and now, write them down.


  1. Trip purpose. You will need to decide on the purpose of your trip. Consider:
  • Are you looking for an adventure?
  • Do you need time to just chill and relax?
  • Is this a romantic vacation? Family vacation?
  • Will you need to take work or studies along with you?
  • Do you want to attend a particular event (conference, workshop, training, family function…)?
  1. Who is traveling? This may or may not be a choice. More than likely, if you have a family, particularly with young children, you are going on a family vacation. However, depending on your trip purpose, you may have the option of traveling by yourself, or with others. If this is the case, here are some things to consider:
  • What is my comfort level?
  • Do I feel safe traveling by myself? (You can read about the benefits of solo travel here).
  • Am I prepared to organize, prepare, and travel by myself, or do I prefer to travel with one other person, or several others?

If you determine that you would prefer to travel with others, you will need to put out some feelers to identify those who have similar time (and/or money), and are interested in traveling with you. Talk to others about possibly planning a trip. If you determine that you would prefer to travel with others, but don’t have others to travel with, consider if you would be comfortable joining a group or tour package.


  1. Decide how much time you have. As an educator, I have a lot of holiday time, but these are fairly pre-set and inflexible. I know in advance that I will have approximately 10 days during Easter and Christmas holidays, and up to 50 days or so in the summer. This may or may not be the case for you. Ask yourself the following:
  • How much time can I comfortably devote to my next travel experience?
  • Do I need to request this time off from work in advance?
  • How long can I be away from my job?
  • When I am away, will I be losing time or money?
  • Do I have other activities that I need to put on hold while away?
  • How many trips do I want to take this year?

Once you know how much time you have, you will be able to begin culling your destination list. Some destinations will be obviously out of your time scope. Others may be more difficult to determine, which brings me to step number 5.

  1. Create a tentative itinerary for each possible destination. Whether you have the time, money, or energy to explore an area is often determined by its proximity and accessibility to you, how large an area you wish to explore, or what activities you wish to accomplish during your trip. However, you may not know the extent of these factors until you actually map out the possibilities. I create extremely detailed itineraries for all destinations that I am considering. (I’ve attached examples of some of my itineraries to this post – Ethiopia 2014 Egypt 2013 Turks & Caicos 2013). Sometimes I refine these and use them, while others are used for planning purposes only and are set aside for future travels, or discarded altogether. What to include in your itinerary:
  • Begin your itinerary by listing the number of days that you are prepared to travel (ie. Day 1 – Sunday, June 22, 2014; Day 2 – Monday, June 23, 2014…). You will immediately be able to visually prepare for each possible travel day.
  • Research your mode of transportation. What is the best (ie. most cost savvy, convenient, time efficient) way for you to get to your location? Consider all options – flights (how to find affordable flights), trains, boats, buses, personal or rental vehicles, bicycle or foot travel…note the cost and time that it would take for you to use any of these modes of transportation. Keep in mind your own comfort level, as well as those you are traveling with. I once mapped out what I thought was a perfect itinerary, only to find that my ex-boyfriend was not comfortable taking red-eye flights.
  • Thoroughly research the sights, activities, and events that are occurring in each destination. (I will be breaking this down in subsequent blog posts). Note which ones you are interested in, and decide how much time and money it would take to complete any of these. Create a tentative “daily schedule” to see how much time you need to spend on each. Consider the time it takes to get to and from an area, and if you could do these things by yourself or would need to hire a guide or join a group. Remember to factor in time and costs for renting any special equipment (eg. guides, surfboards, yoga mats, diving equipment, boats, etc…). Keep your options open.
  • Look for possible accommodations. Consider if you are traveling during high or peak seasons, and if accommodation will be difficult to secure. Here’s my guide on finding affordable accommodations.
  • Keep a running tally of both required and optional costs for each day of your tentative itinerary.


  1. Make a decision. Now that you’ve created detailed itineraries for each destination option, it’s time to carefully compare these and make a decision. Ask yourself:
  • Which of these itineraries appeals to me the most? Are there enough activities to interest each of the travelers?
  • Am I prepared to save/budget/spend the approximate amount that each itinerary amounts to? Remember that the costs you researched are only estimates. You will need to also factor in real costs such as food, accommodation, gas/mileage, childcare, and any additional purchases. You may also have unexpected costs such as mechanical, or other repairs.
  • Do you have time to obtain any letters of invitation, visas, or immunizations that are required by the destinations you are considering?
  • Do you have time to organize tours for yourself or will you need to hire others to help you?
  • Is safety a concern? What is going on in the area during the time you wish to visit? Are there any applicable travel advisories?

The most important things to remember when choosing a travel destination, is to do your research, follow your interests, consider your comfort level, and remain flexible. The best travel experiences are just that – experiences. Start creating your next one now!

Need help planning your travels? How do you decide where to travel? Leave a comment, and check out my travel site to get you started. I’d love to hear your ideas for inspiration! You might even join me on my next adventure!


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