How I Plan a Trip

Everyone knows that at airport security, you stay with your carry-on bag until you’ve pushed it onto the conveyor belt, right? Going through security at the airport is one of my least favorite activities, and I think we all have a common goal of wanting to get through it as quickly and painlessly as possible.

So, here is a very real exchange between a random girl (RG) and airport guard (AG) from when Gary and I flew to Orlando, Florida from Baltimore, Maryland in December 2018.

AG asks RG to put her bag up on the metal part of the scanning machine and to stay with it until she pushes it onto the conveyor belt. RG puts her bag up on the metal portion of the machine and then gets in line for the people scanner.

AG: Ma’am please stay with your bag until you push it onto the belt and then get in line.

RG: You TOLD ME to put it up on the machine and get in line.

AG: No I didn’t ma’am, I told you to stay with your bag.

RG: I KNOW HOW TO FLY I DO THIS ALL THE TIME.

She proceeded to argue with him for five more minutes, holding up the line and making everyone wonder if a bus to their destination would be faster.

The point of that story is, don’t argue with airport security unless you’ve got a really good reason. I love to fly and being in an airport is exciting to me, but no one loves going through security.  I pride myself on being able to get through security quickly and painlessly. In fact, it’s one of two things I’m really good at in life; along with planning trips. Gary sometimes reminds me that I’ve taken him on the best trips of his life and I like to remind him that he’s fortunate to have his own personal travel agent.

So, as I prepare to head to Philadelphia this weekend and Sedona next month, I thought it would be good to write down my planning process for trips.

Destination

In my little family of two, I am usually the one choosing where we travel. I tend to get ideas from places I’ve written about in my previous job at a travel agency or from one of the many travel groups I’m in on Facebook. I’ll see someone post pictures of their trip or ask for recommendations about a destination, and then it’ll pique my interest. I try to choose places that are varied, meaning a mix of cities and natural wonders. There is just so much to see out there and I do my best to make sure we see as much of it as possible.

Accomodations

I’ll usually look up flights and hotels (I personally use hotels.com a lot because they have good rates and a lot of hotels have free cancellation/delayed payment). For flights, I like to use Google Flights, SkyScanner, or Kayak. Something  I’ve learned to dio is book flights in incognito mode on Google Chrome because airline sites will use cookies to know if you’ve been searching for flights and will raise prices. Gary and I also have gotten into the habit of traveling off season (full disclosure though, we are able to travel anytime during the year because we are a child-free couple and I recognize this is not a privilege everyone has), and it has saved us a decent amount of money. We also tend to avoid flying out on weekends because I have found that flying on a weekday can save a decent amount of money. When I’m looking for a hotel, I first decide if we’re driving there or flying. If we’re flying, I usually look for a place within the city center for easy access to attractions and if we’re driving then I’ll save money and stay 10-15 minutes outside because driving in will be relatively simple. I’ll usually choose a hotel that’s in the middle: not too budget (learned that lesson in Ohio) and not too expensive because we’re budget travelers who like to save money for coffee shops and random markets.  As long as it’s clean and the bed isn’t hard as a rock, we’re good to go.

Things to Do

This is my favorite part of planning a trip – finding what we’re going to do! For me, researching is half the fun, I love to map out a loose schedule of the popular attractions and the hidden gems. I try not to over schedule a trip but I also don’t go in blind. Usually the first place I check for information is Lonely Planet, I used this website heavily when I worked at the travel agency and it’s a great resource for finding ‘must do’ things in each destination. Of course, I also use Pinterest which leads me to a lot of travel blogs. I love reading first hand accounts of places because that’s how I find a lot of hidden gems of each place. A great example is Second State Coffee in Charleston, South Carolina; I would have never known about it without reading a blog about Charleston. It ended up being one of the highlights of my trip (if you’re in Charleston, go to Second State Coffee and order the lavender latte and blueberry scone – you won’t be disappointed). My final tip is to check out the tours in your destination. I’ve done two tours with Free Tours By Foot and they are always the first place I check. I love walking tours because you get familiarized with the city, learn about significant historical sites, and get to connect with fellow travelers.

As the person planning the trips, I find myself getting a lot more excited than Gary. Everyday I’ll be saying to him, “I found this new awesome thing to do while we’re away, are you excited?” and he’ll respond that he’ll get excited closer to the trip.  I’m hyped as soon as I start to plan the trip but Gary doesn’t really get excited until we’re physically sitting in the plane. Maybe next time I’ll let him plan the trip from start to finish.

Follow me on Facebook and Instagram!

Leave a comment