I love planning trips. I actually love planning a little too much that I had to limit how much I was planning a trip. I try to get the most out of every trip. I want to see all the things that make that area popular and stuff that might get overlooked. When I planning to visit a place, I have the mindset that I am never coming back. Sometimes I have planned a trip so much that I feel like I have already been on the trip because I had done so much research. When I plan a trip, I have learned to not start planning until 6-8 weeks before the actual trip. There are a few trips that are exceptions but for the most part I try to stick with this guideline.
I have an ongoing list of places that I want to visit. I typically do most of my traveling spring – fall. I live in the midwest and I don’t like snow. Unless I don’t have to travel or the weather is perfect, I don’t travel. I have only been back in the midwest for about 18 months, so I’m wanting to explore more of this area. Even though, I grew up in Iowa I don’t remember going to Illinois. So I’m super excited to explore my new home.
The Preparing Stage
If you follow me on media, been here a while or know me in real life you know that I am a planner! I have tried to go with the flow, but I can’t. I have given up on going with the flow and embracing I am a planner! I have a growing list of places that we want to visit in my planner. Once I have decided on a place, I create a google sheet to plant he trip. If multiple people are going on the trip, I create a sheet with everyone whoever is going on the trip. Then each person gets send a link to the document so they are add what they want to do.
ORGANIZATION TIP: I tell everyone if someone already has what you want to do put it on the same row. For example, when we went to New Orleans everyone wanted to go to Bourbon Street. So on the document Bourbon Street was in the same place. It’s easier to see what things a large group of people want to do.
I use a variety of websites to find things to do in the places that I am visiting. For me I always like starting with a hotel. I like knowing that I have a place to stay then factoring everything around that. I use Booking.com for hotels. I will also use airbnb if I am looking for something that is different or unique. I am also starting to get into car camping, so I use The Dyrt or FreeRoam.
I look in a lot of different places to figure out where I want to go. First I start on Trip Advisor to see what’s recommend to see. Sometimes I already know of places, but it’s nice to get more of a variety of things to do in whatever town. I love finding things that I didn’t know existed. Milwaukee Public Place was in the top 10 of things to see while in Milwaukee. It did not disappoint and I highly recommend going first thing in the morning.
Next I moved to social media and search hashtags. I love when people share how to do a certain city under $20 or free things in the area. In my opinion this has been in the best way to find more local things to do. If I am not ready to stat planning, I create a saved folder in Instagram. By searching hashtags, I find people who live in that area and sometimes I message them that I am coming to visit and looking for things that aren’t so popular.
This is the fun and also terrifying part of traveling. I love planning BUT if I am going with a group I want everyone to have a good time. I am people pleasing over thinker so making sure everyone has a good time and gets to do their top things is important to me. If it’s a solo trip, I keep a running to do list of things that I want to see and do.
The next step in the planning stage with a group is creating an iternary. I create a new sheet in google with the hours are in the first column, and the days we are going to be gone in the first row. I start the day out pretty early around 5am and finish the day around 10pm. I do this in case we want to go somewhere super popular then it’s the first things we do in the morning and usually pretty early. For example, when I went to Vegas I wanted to do Valley of Fire. It’s about an hour away from Vegas and was recommended to me to go earlier in the day.
Then we start planning and putting in time slots. Sometimes are easier than others. When Gary and I travel we like do as much as possible. We don’t want to feel rushed or on a time schedule but we want to fit as much as we can into each day. We both have in our heads the #1 thing we want to do and make sure that gets done either by doing it first or making a reservation for it.
If it doesn’t get scheduled it stays on the list because we might do whenever we feel like it. When we went to Vegas, I wanted to go to the Linq but didn’t create a time for it because it’s right across from where we are staying. We can do that anytime.
Some people check the weather, but I am not one of those people. I am always cold so I always have leggings and a sweatshirt with me. It doesn’t matter the season. I tend to bring at least 1 pair of leggings or pants and 1 long sleeve or pullover. If I am flying I usually wear the most amount of clothes to make room in my bag. I try not to check a bag if I don’t have to so I try to be very strategic with what I bring.
When I pack I use packing cubes because my bag is more organized and gives me less anxiety. I usually pack like items together in each cube, but I have packed a whole outfit in a cube. Both work just fine but it depends on how long I’ll be gone and what I pack. When I pack ahead of time it’s usually packed by outfits. Also we if are doing a lot of things and need different clothes I pack by the outfit so I can grab a packing cube and go.
I use a checklist of things that I need to pack to make sure that I pack everything. I’m currently trying to bring only things that I know I am going to use. The checklist helps me stay on track. Sometimes I write it out and check it off. I have created a google sheet before listing everything for each day and things that I will use everyday.
I try to be as organized as I can before traveling. So when we leave I can just enjoy being in the moment and the trip. I use a lot of different resources to find where we want to go because I really want to explore the whole city or region not just the popular stuff.