Where to Wednesday - How I Plan My Trips

TL;DR. I plan my trips pretty much like everyone else, with maybe a bit more research into where I want to stay, things I want to do and places I want to eat at, but ultimately, the planning process looks pretty simple like this:

1) Choose the destination (in our case, PULL the destination)

2) Decide the most optimal time of the year to visit

3) Books flights and hotel (in no particular order)

4) Research and create itinerary for how you want to spend your time! Nothing super strict, just a general list of things you want to do each day.

5) Count down the days!

But to get more in depth…

First and foremost, how do I decide where to go? Well, my fiancé Austin and I actually have this jar… We made it in 2018, an idea I found on Pinterest, both of us writing down the many destinations we long to visit. Some were super simple, a city, state or country, while others could be a bit more specific, like Amsterdam in the spring to see the tulips! Every year on New Year’s, we each pull from the jar.

2019, we pulled Seattle and Boston.

2020, we both pulled Paris (fate, right?), but unfortunately we couldn’t go through with that trip for obvious reasons… :’(

2021, we actually didn’t pull because we were uncertain on the travel restrictions and didn’t want to be let down again.

2022, we pulled Switzerland!

2023, we switched things up by pulling two each, instead of one each, AND we picked a bonus. This was all Austin’s idea since we were strictly picking United States/North America this year. We picked Toronto (for a baseball game), Philadelphia (another baseball game), Pacific Northwest camping trip, Inner Basin trail in Arizona, and the bonus was Universal Studios. I honestly just wasn’t super excited about these options and we actually ended up putting them back a few weeks ago to pull again in the future. We may or may not have something else entirely up our sleeve, but we’ll see.

While this years pulls were a bust, typically we DO stick to the places we pull, minus 2020 and this year. We did in fact go to Boston at the end of March/beginning of April for Opening Day at Fenway (something we were supposed to do last year, but the MLB lockout pushed the schedule back a week). Boston almost seems like a yearly ritual for us, no matter what we pull.

But now you’re probably wondering, what happens once we pull a destination? I go into hardcore research mode, that’s what.

I LIVE for the research that comes with planning a trip. And the lists! Of course I have an ordinary Bucket List, but once I know that we’re heading to a certain somewhere, I make a specific list of places to see, things to do, and what to eat that I must complete before returning home specially for that place. Naturally, deciding WHEN is also one of the first things we do, usually spring and October being our preferred travel times, depending on the destination. If you read last weeks post, you may know that I loathe traveling in the summer if I can help it.

In 2019 when we visited Seattle, we went over my birthday at the end of April. Our Boston trip that year was at the end of October/beginning of November. A little late for peak fall-foliage, but we at least got to see fall colors AND visited Salem on Halloween Day.

Even though in 2020 we didn’t get the chance to go to Paris as we had hoped, we were planning on that being our October anniversary trip, we instead road tripped in the Jeep to Arizona and Utah in October, visiting the Grand Canyon, Horseshoe Bend and the Mighty Five National Parks. That was a great time to visit in my opinion, since the parks didn’t have the summer crowds - or the heat! The weather was amazing for us until it snowed one of the last couple days.

2021, we visited Boston at the end of September for our (early) anniversary trip and to catch the last Red Sox - Yankees game of the season. The weather had cooled down nicely but it was a bit early for fall colors at this time.

2022, of course we chose to go to Switzerland in October, other than Boston again in the spring. We were in Switzerland for mid-to-late October and the weather was fabulous!

Yes, we’re that couple that takes a trip, whether big or small, for every anniversary, so just assume if it’s October, we’re most likely going to be gone somewhere at some point during the month. But this is a part of the deciding process for when to go where from what we pulled.

We pick the time of year we want to travel to whatever the destination might be, we discuss how long we want to be gone, we look at flights for a range of dates, we book it. Not immediately after pulling, of course, but after a bit of research at least. We start looking at accommodations, whether that be via Airbnb or hotel chain. When we decide on a place, we book it. And sometimes that could be before booking our flights, in the instance that we're waiting for the prices of the flights to go down.

As I mentioned before, I absolutely love the research part of planning a trip, so that also applies to finding where we lay our heads at night. Usually, if I can’t sleep, I’ll open up the Airbnb app, making folders for specific destinations for future reference, and adding any spots in our price range that appeal to me, or I’ll scroll through Pinterest and update the boards I have for each destination I want to visit.

For flights, I generally look on Google Flights or through one of our credit cards.

For accommodations, Airbnb is a favorite but we’re certainly not opposed to hotels. I’ll use Booking.com or book through the actual hotel, depending on the price difference.

Where do I look for what to do on the trip? Where to eat? What to see? Everywhere! Pinterest, Instagram accounts I already follow, I’ll even buy a Lonely Planet travel book (yes, I love that these still exist), and of course, good ole’ Google. Since I’m very fond of history and photography, I always include lots of options where I can soak in the history of the place in a way that interest me and locations of spots for some dope photos. Austin and I also tremendously enjoy food, so eating good while on vacation, trying the local cuisine and popular favorites, is a huge priority for our trips!

As always, these are just my opinions on how I like to plan trips, which isn’t too different from normal. I’m extremely grateful to the people in my life that have shown interest by asking for my traveling advice or asking me to make them itineraries for their trips. It’s been a huge motivator in sharing how I prefer to travel, but just keep in mind this is just my preferred way and not the only way. Hopefully it helps expand your knowledge and the betterment of your future vacations.

So where to?