February 9

3 Questions to Ask to Figure Out Where to Travel Next


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This is a pretty loaded question, but honestly, it’s one of my favorite things to help clients with. I’ll step you through how to evaluate the time and timing constraints and balance that with varied interests of the people you want to travel with.

To get started, ask yourself these three questions:

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1. How much TIME do you have to travel?

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Regardless of the number of days you have available to travel, you want to make the best use of that time as possible.

The further the destination, the less likely you will be to return to that region as frequently as other places. Therefore, my rule of thumb is the further away a place is, the longer you should spend there to get the most value of your time there.

Here are some of my recommended trip durations for those of you living in the US:

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I like to plan out my big trips first (i.e. 1 week or longer) and then fill in the gaps with weekend getaways. Remember, you aren’t constrained to going to just one place – use your vacation days creatively to maximize your time off!

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2. WHEN can you travel?

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Most places in the world have high season, shoulder season, and low season. As much as I love Chicago, if I’m talking to a person that lives in southern California I would NEVER recommend they come to Chicago in January! Clearly, summer is the high season in Chicago, and for good reason. However, there are a few places, like Hawaii, where it’s ALWAYS high season (with Christmastime being the highest of the high season!).

A quick google search for “best time to visit” + the destination you are considering will give you results to help you figure out when high, shoulder, and low travel seasons are there. 

Generally speaking, you get better deals during low and shoulder season and you aren’t battling the large crowds of high season, however you may not get the best weather. I highly recommend traveling in shoulder season when you can since it’s a bit of a balance of both worlds.

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Also, remember that destinations in the Southern Hemisphere have opposite seasons, so right now places like Australia, New Zealand, Argentina, and South Africa are enjoying the height of their summer. This makes me want to hop on a plane to one of these places immediately!

If you can only travel during certain times of the year based on work or school schedules, you may have to go to some places during high season and that is ok as long as you are prepared for that from a budget and expectations standpoint.

My biggest piece of advice for those that have to travel during high season is to BOOK EARLY! Like a year early, no joke. If you are thinking about a summer vacation in a popular place like Europe, you need to get on it! The best places to stay at the lowest rates are going quickly, so all is not lost, but I highly recommend taking action quickly in order to ensure the best overall travel experience.

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3. Who are you going with and what do each of you want to EXPERIENCE?

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Who are you planning on going on this trip with? If it’s a solo trip – awesome, you get to call the shots on the types of experiences you want to have! However, if you’re traveling with a significant other, your kid(s), or a group, then there are others to consider.

Everyone travels differently, so the trick is to find a well-balanced destination where everyone has a little something they can get excited about doing, seeing, eating, and/or learning. Trust me, if the people you are with are not enjoying their vacation, then YOU will not enjoy your vacation!

Have a conversation with your travel partner(s) about what they ideally want on to do on vacation to further narrow down your list of destinations. Do they want to:

  • Take a cooking class and eat ALL the food?
  • Learn a new language?
  • Lounge on a beach with a drink in hand?
  • Volunteer with an organization you’re passionate about?
  • Do something physically challenging, like summit a mountain?
  • Get their adrenaline running with an adventurous escape?
  • Learn about history in the place it happened?
  • Experience zen in a yoga retreat?

The possibilities are endless, but it’s important to discuss this up front so you’re on the same page.

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Take a look at your list of possible destinations – are there any that pop out at you that check the interest boxes of everyone you’re going on the trip with?

If you’ve narrowed down your list, check out how to figure out what to budget for your trip when comparing different destinations.


Comment below where you’re going this year!



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