My Planning Process
“For tomorrow belongs to the people who prepare for it today.”
I am a firm believer in fully planning out any and all trips! Some might say I go overboard with it, but to me it is a safety net. It allows me to make sure that I get to see and do everything in a destination that is a must for me. It is a way to have no regrets - or at least minimize any regret! Just because you thoroughly plan out trips does not mean that you can’t have time to just wander and explore different areas; it just means you have specifically planned time to do this on your trip.
Determine where you are traveling to
Start with the obvious - where to go! This may seem like an easy step, but sometimes there are multiple factors that need to be considered when making this decision. Some of these factors include: budget, using travel rewards points or not, how many days you can be away, etc. You should take all of this into consideration before selecting your destination. Your destination won’t always be your number one wish list destination at the time. For example, say your number one place you want to go is Greece - but you live in the States, have a moderate budget, and only have a week available to be gone. Greece doesn’t tend to be moderately priced, and if you plan to do both the mainland and some island hopping you’ll probably want a minimum of two weeks to spend in Greece.
I experienced a prime example of this when figuring out where to go on our honeymoon as we were on a tight budget. We ultimately decided to go to Aruba because at the time we had the Southwest Companion Pass, lots of points with Southwest, and points saved up with Marriott. This meant that we could fly basically for free to Aruba on Southwest and get our hotel room funded fully on points as well!
Make a list of things you’d like to see & do
Once you’ve determined where you are going, start making a general list of places you’d like to see and things you’d like to do. Start with things you already know off the top of your head, then start looking at your favorite travel blogs to see if those travelers have gone to your chosen destination and what they recommend doing there. Make sure you do not skimp on this step. It will start to feel repetitive at times, but you want to make sure your list is thorough and doesn’t miss anything you’ll be disappointed about missing in the future.
Go through & bold your must hits
Once you are satisfied with your list, go through and be a bit more critical with it. Which items are “I gotta see this!” compared to “That would be nice to see”? It’s best to come up with a system that makes the most sense to you when labeling these in different categories. For me, I bold the items that are must-see. Keep in mind you aren’t narrowing your list down to just must-see places at this point as some of the non-bolded sights may be close or on the way to your must-see spot. If this is the case then it makes sense to include them anyways. Keeping that in mind, do not start deleting any items off your list just yet.
Start mapping out locations to determine best route
I use Google Maps for this. I literally will just go through the list and put all the items in on a multi destination trip. Once you put the items in, you can start rearranging them to be in the order that makes the most sense geographically. Do not do this only with your must-see spots, but rather include all items. At this point, if some of your items that aren’t must-see’s are WAYYYY out of the way, then you can determine that it doesn’t make sense to go to that one and cross it off the list or delete it. I tend to not delete anything and rather “strike-through” it in case I later want to go and add something back in.
Once you have mapped out the most efficient route to your must-see’s, copy that order to your original list and mark how long it takes to get from Point A to Point B along the way.
Begin inputting information into your travel itinerary
Now that you have your order ready to go and the timing listed out, you are ready to start putting the information into the travel itinerary. Don’t forget to download or make a copy of the blank itinerary to use. ***Do not just start editing it from the link, you must make a copy of it or others will be able to access your itinerary and edit it. ***
It is at this point that I also make sure I have all the logistics of my various stops, including: hours, pricing, any tips or trail specifics that I need to remember during my travels, etc. Anything I think may be needed to know while traveling, I put into the notes section of the itinerary, including hours for all days of the week as we haven’t determined what dates/days we’ll be going yet. Sometimes items on the list will determine what day of the week they need to be on and you’ll have to backwards plan from that day. For example: when making an itinerary for us to go to Greece, one of the islands we want to visit only has a ferry available on Saturdays from our other destination. As a result, I knew that day of the trip had to be on a Saturday and I planned everything else accordingly.
You’ll also want to determine how much daily activity you want and are willing to have at this point. Don’t go overboard with this. We will jam-pack things in at times, but typically only for a couple days in a row and then we will plan a lighter day for us to recover afterwards.
Determine what dates you’re going
Now that you have all the information you need for booking your trip, you can determine what dates you’d like to go. Is there a specific season that is better for the area you’re visiting? For example, the New England region of the United States is glorious in the Fall. Or maybe you have a situation like the example above where a specific day of the week was required for one of your items.
Once you’ve picked out the dates that you’d like to go, now is the time to start taking care of all of the logistical things that go along with traveling. Do you have a job that requires you to request off for travel? As a rule, never book anything that is non-refundable until you have written confirmation from your job that your time off is approved! You need to book your transportation required: plane, train, car rental, etc. Also start booking all of your overnight accommodations: hotels, AirBnBs, camping grounds - wherever you choose to rest your head!
Lastly, any attraction you can buy your ticket ahead of time for, I recommend doing so. Booking ahead saves you valuable travel time!
Create a packing list or use one of mine
If you haven’t figured it out by now, I’m a total list person! Once you have everything planned, it’s time to make sure you won’t forget anything when you pack. Start making your own list or use one of my checklists specially designed for different types of trips! If you are doing anything unique on the trip, take extra care to make sure you include anything you might need for that. For example, if you are planning on going scuba diving, include scuba gear and your underwater camera gear on your packing list so you won’t forget them!
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