Shannon Did What / Travel + Lifestyle Blog

How To Plan Your Next Trip Like A Boss

TravelShannon Guerrero1 Comment

I’d have say that I’m a self-proclaimed expert trip planner.  Well, that’s partially coming from praise and feedback from my family and friends.  I mean my cousin just told me I find the best things to do and see on a trip.  I’ve already admitted it, I’m slightly OCD, so I keep everything extremely neat and organized.  Usually in the form of a grid and broken down by category and day.  Although, I admit, that sounds pretty intense, I swear when I create an itinerary its more of a way to show all options of things that can be done.  I always keep in mind that things pop up and sometimes it’s more fun to see where the day takes you.  It’s less enjoyable to stick to a minute-by-minute plan.  That’s just no fun!  I like waking up having a loose plan for the day.  Here are my tips to planning a fun and exciting trip:

Obviously decide where you’re going first!  If you’re anything like me and want to literally go everywhere, this can be a hard decision.  Also, important to decide whether you want to have a more leisurely vacay or a more fast paced one.  It can be a mix, as well, but you should have an idea of this when planning.  For example, in planning my trip to Bali in September, I’m planning on having laid back pool time and adventure days.  In planning my cross-country road trip, the itinerary is definitely way more packed.  Even if you’re shooting to have a laid-back vacation, having any idea of a few things to do is great to keep in your back pocket.

Similar to how I start planning the photos that I’d like to take on my trip, as outlined here, I start with researching what the most popular and main points of interest are.  Honestly, I think a lot of how I plan where to go is by figuring out what are the most photographic spots to visit, but that’s just me!  Life of a photographer I guess!  Generally, these tend to be major landmarks.  Searching for photo inspiration is really helpful because I’ve found I find off-the-beaten path spots that are not super touristy.  On the other hand, I do check Google’s points-of-interest because these are the locations that city is the most known for and you should see the touristy stuff.  I like that you can see photos of them immediately.  There’s no guessing what each location is or looks like.  My most valued resource is to search on Pinterest.  I like to find other’s blog posts on their experiences first hand visiting these places.  I can get an idea of what time of day to go and how long to expect to spend at each location. 

Sometimes after you look up a bunch of great places to see or visit you realize that they are all the way across town from where you’re staying or even outside of the city.  If you’re just dying to go somewhere but its going to be out of the way, why not make a plan so you know you can make it work!  Sometimes, you have to wake up early to get somewhere and plan places to visit on the way back to your hotel or your next stop.  My new favorite tool (that my roommate recently put me onto) is saving locations onto Google maps.  It places stars on these locations so that when you look at the map you can see exactly where everything is.  So helpful for planning my cross-country road trip!

As I mentioned earlier, eyewitness testimonies in the form of blog posts is super valuable in learning how long to allot for certain locations.  You can learn a lot about whether there will be crazy lines or how long to expect to spend there.  If you know approximate timing and of course location, you can plan how many places you can get to in a day.  Reminder, it really depends on you.  Remember how tiring it can get if you’re spending all day walking around, so don’t overexert!

I love including photos of some or most of the destinations that I’d like to see.  This is a great way for the people that you’re travelling with can pick and choose what they’d like to see as well.  I just like to see all of the places to look forward to!

Planning a loose outline for your next trip is great way to not have to do much thinking on your actual vacation.  You’ll have more time to enjoy your trip if you’re not constantly thinking of what to do next.  Just don’t get too caught up in making sure you see everything.  Sometimes it’s just not possible.  Prioritize and then go with the flow.  Guaranteed (don’t hold me to that) you’ll have the best trip!

Yours Truly // Shannon

Ps. I created a little template to get you started with planning your next trip.  Download it here.