Before I get started, I just have to say that I don’t have any sort of spon con agreement with any of the apps or sites I am about to talk about, but hey, if any of them WANT to pay me, I’m free and available. Traveling, ain’t cheap!
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I am organizational nerd. Maybe I am on the spectrum a bit, who knows, but when a multilevel plan comes together, it scratches an itch that is fairly indescribable.
In my professional life, I plan things. They’re mostly micro events, but there are several a month happening. Unfortunately, a lot of the success is out of my control, which can sometimes lead to a bit of frustration, but when it comes to travel planning, it’s really just me against the world.
Travel planning for me starts long before any thought of travel destinations are settled. If I’m watching a movie or a show and I come across a location or restaurant that I want to try, I will typically open up Google Maps and drop a pin into folders I have created for cities I either know I am traveling to or what to travel to at some point in the future. If you were open up my map of Manhattan, it would be littered with pins from the last 15 or so years, and now my network of pins span the globe.
My domestic travel is decided upon by work travel, mostly conferences and the like. I’ve reached a point where there are very few places in the United States that I want to see that I haven’t seen already. This is not to say that places that I never thought I would jive with, like San Antonio or Santa Barbara, can’t truly surprise me, but when it comes to where I want to spend my leisure time in the United States, it is pretty much dedicated to the “2 News” – New York and New Orleans. Ironically, I’m heading to New York this weekend before continuing on for a work trip on Monday.
My Google Maps for international travel are a lot more sparse, with me only starting to research once I decide on a destination. For instance, I really wanted to go to Amsterdam in 2024, but once it came time to look at hotels, there just wasn’t anything in the budget (budget is not strict, I just know what doesn’t fit). It was then when I decided to go to Brussels, which turned out to be one of my favorite places.
Once I figure out the airfare situation, I can start to fill in the rest of the plan. This year, I struggled a bit because even though London is a great city, it just wasn’t close to my continental European stops like Vienna, but for a Chicago departure with American Airlines status and the One World Alliance, London via American or British Airways is really the only affordable option.
Once I settled on London as book ends, then it was just a matter of figuring out how I was going to get to Vienna for Eurovision by May 12th and how I was getting back to London to fly out on May 25th. Beyond Google Maps, here is what I used to organize and book my travel:
WanderLog – https://wanderlog.com/ – Beginning with my 2024 European vacation, I have used WanderLog for every trip I have taken either work or vacation. I even use it for my contract trainers to receive their hotel bookings at work. I mainly use the app, but I really do like the web interface for a better user experience. WanderLog fully integrates with Google Maps and Gmail for a somewhat seamless experience, but since I do most of my travel booking through work emails, I basically just use the unique trip email WanderLog provides to forward everything. It is great way to organize all your reservations including air, hotel, car reservations, transit tickets, and even events. It is definitely worth the less than $50 a year for the premium experience. It also has a journaling section, but since I didn’t want to have my entire itinerary available for anyone to see, I opted for a blog like this.
The other thing WanderLog does exceptionally well is allow you to add points of interests to every day of your itinerary. This is where I start to convert my copious Google Pins into things I actually plan to do. This organization can also help with finding hotels, because once I start slotting in attractions you can start to triangulate where the best location will be to stay.
Once you have your trip broken down into days, WanderLog takes it one step further and will optimize your path to make the most sense for walking or transit. You might find that something you slotted in is just too far away to manage for that day, but then you can just move it to another day where it might fit.
Rail Europe – https://www.raileurope.com/ – I discussed this in a previous blog, but this has been my go-to for booking train tickets for the past two trips. Sure, these trains run frequently enough that you could, hypothetically, book them on the fly or go the Eurail pass route, but I much prefer having everything sorted and going to plan. Rail Europe allows me to do all of this in pretty much one location, though overnight trains seem to be its own thing. Sometimes it can be a little confusing, but if you take your time and research something you don’t understand, you can figure it out. I have faith in you!
GetYourGuide – https://www.getyourguide.com/ – There are several apps and websites that do the same as GetYourGuide, but just like Rails Europe, I really like to have everything in one place. While I do not always book tours and things, GetYourGuide is great for self-guided or individual tickets to attractions, and from walking through Prague Castle on my own to a guided Vampire Tour in Budapest, GetYourGuide seems to have everything I need for my travels.
Hilton – https://www.hilton.com/ – This is more a personal preference than anything else. I’ve held status with all the major hotel brands: Marriott/Bonvoy, World of Hyatt, IHG, Wyndham, and Hilton, and while all of them have their positives and negatives, I find Hilton points to be the most flexible. It all comes down to the slider! When you make your reservation, you can choose between all points, all cash, and a mixture of the two, and the last option is what I made most of my hotel reservations with for Europe. In England, I opted to go all points, because the exchange rate was just that bad, but throughout Europe, I used to slider to get hotels for a certain amount of points and whatever I was comfortable paying. It might be a super small thing, but I like the flexibility of being able to pay a little (and earn back some points) while using points for the rest. For Marriott and Hyatt, it is pretty much all or nothing. For me, the slider rules!
Booking.com – https://www.booking.com/ – If I want to get outside the chains and book something with a more local flair, I have had pretty good luck in places like Prague and Athens with Booking.com. This is not to say I haven’t used places like Expedia or Hotels.com, but I just like what I have found here. For places like New York, I am an avid user of Hotwire.com. New York is so expensive that I throw loyalty out the window for the best price possible.
I’m trying to be better about the lengthy posts. So, I will wrap it up. This is a pretty good overview of how I handle most of my planning. A small addenda, I will say that YouTube is pretty invaluable to when I am looking for unique things to do in a given city. There is a plethora of travel videos out there to help you get a handle on what you want to do nearly anywhere in the world. I’ll also freely admit using AI a bit this time around. I know…I know… But it did help me a bit in some cities.
