How to Plan a Vacation without Stress

In an effort to convince my husband’s classmate to join us on a school excursion, I told her it would be super easy and she could just like steal our itinerary. She looked at me like I was crazy, which I figured was due to the fact that I wanted her to travel with us. When, in fact, she was really shocked that I actually had one itinerary already thought out (when in reality I had multiple itineraries figured out for that trip) and ready to go many months in advance. She then proceeded to tell me about how much stress planning a trip gives her and joked about hiring me to plan her next vacation. This conversation sparked the thought that there are others who would love some help planning their next vacation or holiday.

Every vacation or holiday I go on, I plan well before what I would like to do, where I would like to go, and how much money I would like to spend. Every single vacation. Because I plan well in advance, I am never stuck in an amazing place asking, ”what should we do now?” because I already know what I want to do or at least have a few options ready. That isn’t to say our trips don’t have an element of spontaneity.

If truth be told, they may even have more because we always end up under budget. Because we are under budget, we then have the flexibility to tour that super cool location that costs money or go to that fancier place for dinner or go see an extra show during our holiday. Planning vacations is one of my favorite things to do so that we can have the “trip of a lifetime” every single time.

planning trips without stress

Plan trips like a pro

I never thought I could travel so when Jordan and I started discussing the possibility of traveling to where I used to live in England, I started to plan. If we were going to travel, Jordan & I needed to know that we would be able to afford to go.

I immediately created a planner document with potential itineraries & various budgets, places I wanted to see & how to travel between them, and currency differences. Since I was the one who lived in England I planned the whole trip. Through this document I was able to plan who we would see in what areas & on what days, how much it would cost for us to go, what “extras” we could do, etc. I even found a day or two that Jord and I could go somewhere new together. By planning we realized we could afford to go, so we saved & budgeted and, when the time came, went on an amazing trip. When we returned, we calculated all of our costs and found that we were under budget!

Ever since that initial trip, anytime we look at traveling I utilize this document to plan. We always figure out our budget for the trip and because of the way I plan we end up always being just at or under our budget. This has saved us loads of time and helps us make the most of our limited minutes in the locations we visit. If you would like to try planning through my planner system, subscribe below & I will e-mail you my planner document. You can then follow along the different steps as you plan your next vacation.

Figuring out all the details of your next vacation by planning a travel itinerary & travel location options (including things to do).

Plan a travel itinerary & options

The first decision needed is where do you want to travel to? This should be fairly obvious but there can be some complexity.

When picking where I want to go, I mentally list all the places I would like to visit from absolutely “must see” to “cool to see.”

Let’s say I want to travel to England and are wanting to travel for 11 days (including travel days). First thing I would do is enter my dates in the itinerary page of my planning doc and start exploring where I want to go in England. If England was brand new to me I would visit my Pinterest and explore all the many places I have saved over the years. From there I would pick where I want to go and start to explore options.

When picking where I want to go, I mentally list all the places I would like to visit from absolutely “must see” to “cool to see.” By doing this I have a fairly decent idea of where I actually want to go and can start playing with locations and dates in my itinerary. I usually have room for one “cool to see” location in an 11 day trip. (It is important to be mindful of your traveling time when visiting more than one location, you may need a day to get from one area to another.)

After inputting my “must see” locations into the itinerary, I then play with my schedule to see if I can squeeze in that “cool to see” location. When trying to figure out an itinerary I will fix one until I like it and then duplicate the page to play with another variation. Depending on the length of the trip and how many “must see” locations I could end up anywhere from 2 to 6 itineraries. Using our example above, in one page I have a trip with us visiting one “cool to see” destination like Paris and in another page visiting “Dublin”.

From my last trip, one of my things to do was to walk along the Thames and across the Tower Bridge (by the Tower of London).

From my last trip, one of my things to do was to walk along the Thames and across the Tower Bridge (by the Tower of London).

Things to do

Generally speaking, I have a good idea of what I want to do in the location I chose because that is usually why I wanted to go there. This doesn’t mean that one thing/event/etc is going to take up my whole time. Again, I take to the internet (*cough my Pinterest) to explore all that the locations I chose have to offer. Another huge asset, I think most people forget about, is your public library.

When Jordan and I first went back to England, I knew what I wanted to see because I had lived there.. or so I thought. I still went to the library and checked out a couple travel books on the parts of England we were visiting to “just make sure.” I was so grateful I took the time to explore more. There were so many hidden gems that I had missed in my everyday life there, and would have missed going back, if I hadn’t done some research.

Focusing on each location we are visiting, I list any interesting thing I would like to see by title with corresponding descriptions and websites. I utilize the page called “Places in…” my planner. After listing all of the things, I go back through and select my “must sees” and figure out what is nearby. On a typical day I can plan for one or two major things and maybe be able to slide one smaller thing in (depending on the location). Anything more than two (again, maybe three), is too much. Jord and I would come home exhausted, barely seeing whatever third or fourth thing we went to.

Researching things to do is one of my favorite parts of planning trips. I figure out some big/key things to help base my itinerary around and so that I am able to start searching for flights. Between my initial search/buying flights and actually going I have time to plan all the other smaller things into our itinerary!

Every vacation we go on we have a budget. Budgeting allows you to have more freedom when you are on your vacation.

Budget

Every vacation we go on we have a budget. We plan well in advance how much we would like to spend before we even commit to going. By budgeting in advance, we have time to save for the trip and know our limitations. Utilizing the “Budget” page in my planner, I list out every cost. I like to break my costs into a few categories: travel, accommodation, food, activity, & other.

To give you a better idea of what that looks like, here are some examples of what costs may fit under each category. For a typical trip, I would put roundtrip flights to our initial destination and travel between location costs (trains, rental cars & gas/petrol, buses, or more flights) under the category “travel.” Anywhere we stay, whether it is at a hotel, an AirBnB (save money on your first trip by booking through my link), staying with a friend or family member, etc I put under “accommodation.” I guesstimate $100 a day for Jord & I and put that in the “food” category. Your food budget per day will vary based off of your needs/desires. We just really like food. Any costs related to the theatre, museums, costs to do any sort of thing that we want to do or see in a location goes into the category “activity.” And, ultimately, we often find some things that don’t really fit in the other categories, that I classify as “other.” This could include gifts for your hosts or friends and random things. The categories are there to help you not forget anything as you budget for your trip.

My favorite part of my planner is the “price” vs “paid” section (within the “Budget” page). As I plan my trip, I always round up as I add the costs of things we plan to do/see/eat/etc. The planner calculates your items for you and keeps a running total near the bottom. When I book things or pay for parts of our trip before we leave (like booking travel, accommodation, etc), I enter the price we paid into the “paid” column. That column is added up as well and the total is right next to your guessed cost. All these steps help get us to a point that when we start our holiday we know exactly how much we can spend. Throughout my trip I will keep a running total of what we spend in my normal budgeting app I use and then when we get home enter those numbers into the planner. This is how I know we are always at or under our budget!

Another point to mention is differences in currency. I use an app & website called XE Currency to calculate the cost differences. This is super useful as some times I am not sure how much it will actually be in my country’s currency. However, this just shows live rates & will probably change to some extent when you are there. Another reason why this is helpful is I will watch to see if there are any dips before I leave so that I can take some money (cash, quid, etc) with me. Banks make a small profit when you buy or sell different currencies so to make my money go farther I try to exchange (buy) the country I am visiting’s currency when it dips.

Planner examples

In my planner, you will see example pages from one of our trips. These are there to help you see what works for us and guide you as you customize this planner for your next trip. Instead of recreating this file for every trip, I simply duplicate the planner and customize the details. This works for me but I love feedback. Please share your thoughts in a comment below!

Dedicated to my dear friend Lish, hope this helps you plan for Thailand! 😘

Related content: How to Find Cheap Airfare, A Complete Guide to Google Flights, or Bucket List Warm Weather Getaways

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