How I Plan a Trip

The first thing you should know about me is that I LOVE a good, organized itinerary. I am incredibly Type A. Nothing gives me more serotonin than checking a box or crossing something off a to-do list. I have based entire trips on my desire to go somewhere new so that I can scratch it off of the giant scratch-off world map that hangs above my bed. So there is no better travel advice I can give you than to create a great itinerary and have all of your information in one place. I don’t mean you have to schedule every single minute of every single day. But when your 5 hour flight that was delayed finally lands 3 hours late in the darkness of an unknown locale, you’re not additionally stressed about figuring out the address of the hotel to put into the Uber app while juggling your luggage. You’re not digging through emails or packets of information when you need to give Dave at Enterprise Rent-a-Car your confirmation number. 

A well-organized Google doc for your trip allows you to have all potentially necessary information in one convenient place. I’m talking your flight info, complete with flight numbers, departure and arrival times, and booking confirmation codes; the name and address of your hotel, maybe even a phone number; Renting a car? You’ll need that confirmation number as well. Listen to me. Put it all in a Google Doc. You can either save it on your phone as a screenshot or print it out and keep it in your carry on. 

The first thing I do after booking a flight (okay, maybe even before I book the flight) is to create a Google Doc for the trip. It doesn’t have to be a Google Doc – make a Word document; Write it in a journal; Use the notes app on your phone. But put everything EVERYTHING in a document. I like Google Docs because they are easy to share and access. If there are other people traveling with you, share the Google Doc with them so they have all the information at their disposal as well. 

I will start creating a doc before I finalize any travel decisions. For example, here’s one of my planning docs laying out ideas for a future trip to Eastern Europe.

As you can see, I include several different overall itinerary options, as well as the cost of getting around using the train. I also have how long the train ride is between destinations so I’ll know not to book brunch on a day we have to get up early, or a museum admission at 2pm on a day with a 6 hour train ride. Depending on flight times and availability, one of these potential itineraries may logistically work better than the other, but still accomplishes the same general goals.

Typically my travel Google docs consist of several sections. The first page is my flight info, accommodation names and addresses, any transportation confirmation or ticket numbers, and my TSA Precheck Known Traveler Number — all the essential info you will or even MAY need on your travel day. 

The second section of my doc is the itinerary. I put each day’s date as a header, and then include potential activities, booked activities, meal reservations, etc. underneath. This is super helpful for me both during the planning process and once at the destination. During planning, I include a ton of links to things that look interesting (another plus of using Google Docs for this), and when I’m ready to nail things down, it’s all linked right there for convenience. Work smart, not hard, my lovelies. Anyone you’ve shared the doc with can access the links too and give you their input on what sounds good. 

Below is an example from my Amsterdam doc, which is an absolute masterpiece, if I do say so myself. Please ignore my shoddy redactions of the AirBnB information, but this gives you the overall gist of what I aim for. Flight info is there, AirBnb address, Confirmation code, entry information and WiFi are all ready to go. I believe the weather forecast was added by my intrepid adventure friend Rebecca, but it’s super helpful to know when packing. The bottom half of the page has information about and links to sites we want to visit, as well as booking times and reservation information. Is it possible to be in love with a document? Because, if so, I am in love with this one.

Lastly, I usually create a packing list and break it down by carry on and checked bag. It’s helpful for me to see exactly how much crap I’m trying to bring with me to help pare down the bulk. I try to fit everything into a carry-on roller bag and backpack, but for some longer trips, that won’t be enough. As opposed to hauling around 3 giant bags, I want to be efficient. But I also don’t want to have to buy a bunch of things I’ve forgotten. Ergo, packing list! Below is an example of one of my more thorough (and arguably insane) packing lists I’ve created, complete with pre-planned outfit options for my trip to China and Thailand a couple years back.

I’ve learned a lot about the best way for ME to travel over the years. The itinerary section helps me concretely see my plans for a day and decide whether or not I’m trying to do too much. I have a tendency on vacation to want to SEE ALL OF THE THINGS. But when I do that, I don’t always enjoy myself because I’m stressed out about SEEING ALL OF THE THINGS and making all my reservations on time. Now, I try to book one “thing” per day. Maybe it’s a walking tour. Maybe it’s a brunch reservation. Maybe it’s a timed entry to a museum. But that allows me the flexibility to change my plans on the fly and not run myself ragged (or lose any money on deposits for missed activities).

Another thing you absolutely must do is reach out to your network of friends and family. No matter where you want to go, I can almost guarantee you know someone who has been there. Maybe a cousin lived near where you are going, or a college friend took a trip to the same country a couple years back. Ask for their recommendations, have them tell you things that they did that weren’t worth the time, or struggles they had. The internet is obviously an excellent resource, but it is no match for real-life experience. This is especially helpful when it comes to transportation options – how far was the shuttle to the rental car lot? What did you do when the train from the airport wasn’t running? Are there actually places to park, or are you better off relying on rideshares?

I am also a proponent of a good, old-fashioned guidebook. You already know how much I love Rick Steves, but even if Rick doesn’t have a guide for your destination, try to find something that you can dogear, mark up, and carry with you. Believe it or not, technology will sometimes fail you, and in that moment, it is exceptionally helpful to have things like a physical map, the address of your hotel or next activity, or some emergency phrases in the language of your destination. All of these things (and more) are included in good guidebooks. I am glued to my phone as much as anyone, but a guidebook can be indispensable. Plus it gives you something to read on the plane!

I’ve created a little sample travel Google Doc that you can find here. Feel free to copy and paste to your own program of choice as you start planning your next adventure!

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