Planning A Trip: Inspiration

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Traveling is one of my favorite parts of life.  I love exploring new places, whether it’s a two hour drive or an eleven hour flight away, and so this makes deciding where to go on vacation the most exciting part of planning a trip!  It’s also only natural that it’s the first part in my “Planning A Trip” series!

In the front of my travel notebook (yes, I have one, and it goes everywhere with me-but we’ll get to that later) is a quote that I like to remind myself of regularly, especially when I’m ready to go on a vacation.

What kind of destination leaves your heart happy, or makes your mind wander with ideas?  What kind of destinations feed your imagination?

Go There.

For me, this place is somewhere filled to the brim with personality and culture.  Somewhere with a great food scene, and a place where the “things to do” aren’t just museums and monuments, but places with soul and vantage points that make you feel so small, or a street that takes you to another place in time.  It took some time to admit that places that excite other people (all-inclusive resorts in the Caribbean that you never leave, for example) are just not for me.  And that’s okay.  You should never spend your vacation time and money doing something you don’t actively want to do, just because everyone else likes it.  And if waking up at 6am to catch a sunrise isn’t your jam, that’s okay too!  I recognize that my energy level is overwhelming and does not exactly match everyone else’s (even my own sister, sometimes).

If you don’t already have a very specific idea of the type of traveler you are, there are a few types of questions you can ask yourself.  Are you looking to explore or relax?  Does weather matter?  Are you looking for a cultural immersion or a list of attractions to see?  How important are meals, the outdoors, and the amount of required walking to you?  Once you answer these questions, a clear idea of your ideal vacation will present itself pretty clearly.

Even though I know exactly what type of vacation I love, I have such a long list of places I want to see, it usually still requires some narrowing down with follow up questions.  Once I’ve decided it’s time for a new adventure, I usually follow this general formula.

  • Who am I going with?  Whether it’s my sister, best friend, mom, or boyfriend; who I’m traveling plays a big part of where I’m going on vacation.  For example, my sister and I do best together in cities where there’s a lot of activities (think NYC, Nashville, Chicago), while B is my best bet for a place that I just want to wander and take in the culture or scenery someplace (Vermont, Coastal Maine).
  • How many days can I go for?  The next time I only have four or five days to travel, I’m hoping to go to Charleston or New Orleans.  Both flights are under 4 hours, nonstop from Boston, meaning we could be there and exploring by lunchtime.
  • What’s on sale?  This one kind of makes me laugh, but it’s true.  Jenn and I knew we wanted to go on vacation to celebrate our Friendiversary, so we looked at the sale Southwest was having.  The flights to Austin were the best nonstop, so we booked them.  It was one of the rawest, coolest places I’ve been, and I’m so glad the sale brought us there.

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If we’re being honest, Pinterest and Instagram play heavily into inspiring me to visit certain places.  There’s an endless stream of drool-worthy locations being paraded in front of us, and every time I see one that stops me in my tracks, I make sure to file it away mentally for a future trip.

My travel notebook is where I keep track of my highlight reel locations.  It ranges from my ultimate dream trips (Marrakesh) to the top of my general travel bucket list (the Pacific Northwest) and very attainable trips (Charleston).  Every time I’m on Instagram, or talking to a friend, or reading a magazine in a waiting room and see a restaurant, sight, or attraction at one of these places, I always try to remember to jot it down in my notebook under the corresponding section.  This seems really excessive to the average person, but again: traveling is one of my passions, so planning trips I’m not even taking is right up my alley.

What are some ways you gather inspiration for your trips?  Let me know in the comments, and make sure you stop by next Wednesday for the next installment of Planning A Trip!

xo, C

(The first picture in this post is from Hawaii, the last is in Bermuda).

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