Over the last six months, I’ve done more trip planning & created more itineraries than ever before. My most successful plan so far was my first trip down to SF to visit Nathan in May. I combined everything I knew about how we travel with what I’d learned on our previous trips to make the most amazing itinerary. As someone who loves travel planning almost as much as the travel itself, this was immensely satisfying.
This week, I’ve been working on an itinerary for our visit with Nathan’s sister & her boyfriend. They’re coming to stay with us for an extended weekend & we want to do all the things. Since planning is fresh in my mind, I thought I’d share some of my best tips, & a few of my favourite apps that make it all a bit easier.
Find the types of resources you enjoy reading.
It’s so much easier to plan if you’re actually reading about things you enjoy. If you love art & history, maybe some of the travel guides are a great read for you. More than likely though, there’s a website or magazine that highlights your interests more specifically & can give you tips on what to see & do. à
For me, I generally turn to food-related articles, so Bon Appetit is always the first place I check. They’re starting to have a nice selection of city guides that I highly recommend checking out if you like to eat. Otherwise, The New York Times, Eater, & Anthony Bourdain (he just launched a travel website, but you can also search any of his shows online) are my go-to resources for getting the ball rolling.
Create a personalized map of your favourite places
Once you’ve started research, you’re going to need somewhere to store all that data. My absolute favourite travel app is Google My Maps. I can’t recommend it enough & use it daily when I travel. I’ve been using it for a few years now, but they seem to be trying to bring more awareness to it lately, & I’ve found myself using it much more heavily this year.
My Map for the Bay Area
Basically, it just allows you to create custom maps. You can personalize them & then share, collaborate, & take them with you anywhere. I made one for every city we visited in Europe & then shared them with our crew. You can access them from the Places menu in Google Maps, so they’re easy to locate on mobile.
I’m a pretty visual person, so I find this is a great way to start sorting through what I might want to do in a city. I can easily see what places are close together without getting bogged down by stuff I don’t care about, & build an itinerary from there. My Maps will still show things you haven’t saved, but since I personalize my icons, they don’t get in the way. In addition to visual customization, you can also add your own notes to a place once you’ve saved it to your map. This is a handy little reminder for why I added a place or for other little details, like “bring cash!” or “skip the line by getting takeout”.
My notes on Powell Street Street Car
I have maps for most of the cities we’ve visited now & they come in handy any time we revisit. I love researching new restaurants & things to do, so mine are all pretty full. That can be overwhelming for a lot of people. The beauty of these maps though is you can make them as busy or as simple as you like – it’s all based on what you enjoy! Well done, Google.
Close up of my SF Map
One more thing I should mention: these maps also seem to work with offline areas, which is great for when you may not have a ton of data to use, but still need navigation. Download the offline area for any major city & you’re set!
Flesh out an itinerary
Everyone travels differently, & I know the idea of having a plan sounds totally awful to many of you, but I tend to want to cram a lot into a small amount of time. When you only have a few days somewhere, a plan can help alleviate disappointment. At the very least, I like to make a couple dinner reservations & then look at a few other things that are nearby. Lately, I’ve been building my itineraries in Word since it’s incredibly simple, but I’ve also used Evernote, Google Keep, & my calendar for storing ideas. Anything that allows you to keep a few short notes & ideas for when that jet-lag takes hold is perfect for this.
Sample SF Itinerary in Word
In May, we crammed a crazy amount of stuff into a long weekend. Most of this was possible because of all the research I did. It was probably the most intense itinerary I’d ever created. I prefer this style to the more “we’ll see what we feel like” style we’ve gone with in the past, because I find I spend less time doing research while I’m on my trip. Instead, I get it all out of the way beforehand & if I don’t end up feeling like doing something, I don’t have to, but I don’t waste time looking up ideas for things to do on the fly.
Save it all to Dropbox
Dropbox has been around for so long, so this is nothing new. It’s a great way to access files when you’re away from your computer, or share & collaborate with others. I like to save all my travel-related files to a folder I can access when I get to my destination, & Dropbox does this seamlessly.
My travel folder contains pdfs from travel websites, google maps directions to certain places, all my itineraries, any pdf e-tickets I’ve purchased in advance, & copies of our passports & travel documents. It’s all in one easy-to-access spot (just make sure you can connect to WiFi, have data, or make it available offline!).
& that’s mostly it! That’s how I stay organized for our trips & cram in as much as I do. If you have any tips of your own, or would like to see some of my crazy travel maps, let me know in the comments. Happy planning!
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