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Catch Up & How to Decide Where to Go on Vacation

Team.  I’M BACK!  It feels like I’ve been gone 17,000 days, but it’s been 11.  Eleven insanely amazing days that I can’t wait to share with you.  I’ll be sharing details in the coming days (be looking for travel guides to Lima and Cusco, as well as descriptions of hiking the Inca Trail), but at a high level…

…Ray and I booked a trip to Peru the week before we got engaged.  We’re kind of calling it our “pre-moon” at this point, but hey, who knows the direction we’ll decide to take within the next three month.  Either way, we went to Peru to hike the Inca Trail to Machu Picchu.  It was the most physically challenging thing I’ve ever done, but it was incredibly life changing.  Updates to come within the next couple of weeks.

But first, let’s talk about how we decided where to go!


Throughout my grown vacationing life, I’ve regularly been the trip planner.  Whether trips with my girlfriends or with Ray, I’m the one that thinks that no trip is impossible and does the fun digging to find out how to get it done.  But just as important as planning the trip, is picking the perfect location that fits what you’re hoping to get out of a trip.

To make sure that I’m picking the right location, I have two processes.  Either way, I usually like to find my traveling companion first and plan based on how they define “relaxation.”

1) Wish List

I first have a list of places that I reeeeeeally want to visit.  All are places that I have not been to, but I’m understanding that there’s a right time for everything.  Our globe’s tectonic plates are shifting, but the likelihood of a place I’m wanting to see being completely gone in the near future is fairly slim.

Who are you traveling with and would that place be on their “must see” list?  If you’re hoping to see whole assortment of historical sights in Rome, but are traveling with a lay-out/beach lover, then plan your Rome trip for another time.  If you’re travelling companion wants to stay up and fiesta until the wee hours of the morning, then a low-key, restful stay in the BVI shouldn’t be in the cards.

If I’ve determined that the place would make sense for both myself and my traveling companion, I check out the weather around that time of year.  While we were cutting it close planning to hike the Inca trail at the very end of their rainy season, I definitely would not have booked this trip in the heart of their bad weather.  Some things to think about – if you’re booking in Summer, consider trips in the Northern hemisphere; Winter, consider the Southern hemisphere.  This will give you the best chance of having good weather wherever your travels may take you.

Should the place I want to visit either not makes sense for my travel partner or not make sense weather-wise, then we move on to step #2…

2) The Questions

I simply send the person or people I’m traveling with a series of questions:

  • What type of mood are you looking for in this trip? (Relaxing, Adventure, Museums, etc.)
  • Are there any places your wanting to avoid? (My personal answers would be places in civil war, but if someone is wanting to avoid Zika virus, then I wouldn’t include those relevant locations on the list.)
  • How much are you interested in spending? (Generals work, but I wouldn’t be planning a trip to England if your companion is wanting to pinch pennies.)

After hearing the answers to these questions and researching weather around the globe at the specific time of year you’re interested in, I’ll provide around three general ideas.  Simple generalizations should work, something similar to:

Croatia – Zagreb, Slavonia, sailing in the Adriatic Sea

Pros: Great weather, affordable once you get there, easy to travel around

Cons: Difficult to get to from the US, do not speak the language

I ask my travel partner to do their own google searches and decide from there.  Then… Consider it done!  Plus, you’ve already got some ideas to get the planning process started.


How have you planned some of your favorite trips?

Do you usually travel with the same people, or do you like to mix up your travel groups a bit?

Create a great life!

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