I'm in the middle of planning an upcoming trip, and the experience has already reminded me just how much I enjoy this part of the process. That's right, I actually love planning trips, even though I can't say that's true for a lot of other areas of my life. I'm usually a very go with the flow kind of person, and I don't like being weighed down by an abundance of to-do lists. But there's something about traveling that brings out a more type A personality side of me. And to be honest, it really comes in handy.
I look forward to planning almost every detail of my trip because not only does it make me more excited as the date approaches, but it helps me be confident that I'm getting the most out of it. This is the general process I usually follow.
Step One: Research on Pinterest
If I had to choose one site as the ultimate resource for planning a trip, it would obviously be Pinterest. I mean, this is the one place you can go for hundreds of blog posts about other people's experience in the places you're visiting. I always create a Pinterest board when I'm heading somewhere new and then spend hours reading people's advice and tips. It's as simple as searching [Name of city you're visiting] [# of days of your trip] Day Itinerary. Pinterest is how I learned about the best 3 FastPasses to schedule ahead of time at Disney World (which saved me so much time at the parks) and where to find the best meals in Chicago, so it's the best first step for me. Here's a link to my Pinterest if you want to see some of those boards.
Step Two: Create Pins in Google Maps
Once I've made a list of places I really want to visit based on my Pinterest research, I open up Google Maps and add pins for each location. It doesn't actually have to be Google Maps of course, but relying on a detailed map of the entire area you're going to visit as you plan is a life saver. I always plan where I'm going to eat or visit based on location. So if there's a restaurant I want to visit in Manhattan, I'm not going to just randomly head there in the middle of the day if I'm not going to be doing anything else around it. If it's a place I must go, I'll try to schedule some other activity worth doing around there, so I'm not traveling to an area for the sake of just one place. The point is, mapping out all the things you want to see during your trip will help you properly group activities together. Bouncing back and forth from one area to another is a waste of time, not to mention expensive. You can see a map I created for a trip to New York here.
Step Three: Build an Itinerary
I usually build a travel itinerary for my trips using Google spreadsheets, so I can access it wherever I am. It's as simple as creating rows for each half hour, and columns for every day of your trip. Here's an example of my itinerary for my trip to New York last fall, which was a little fancier because I actually printed it:
Now of course, this calls for a couple disclaimers. When you are traveling, especially when you visit a new place, you're not going to be able to perfectly predict how much time you'll spend somewhere, or how long it'll take you to get there. Stuff happens, and flexibility is absolutely essential if you want to actually enjoy yourself (so much on my itinerary above didn't happen, or got pushed back). So while I do create these hour by hour itineraries, I'm always careful to give myself as much time as reasonably possible, and I always go in with the mindset that I am absolutely not going to be able to stick to the itinerary perfectly. An itinerary is supposed to be a tool to make your trip go more smoothly, not something that's going to stress you out and take the fun out of it. So, take it with a grain of salt. I do think they're worth making, but they're never worth stressing out about.
Step Four: Have a Backup Plan
Every great plan has a backup plan, and this also goes for travel plans. I don't mean you need to create a backup itinerary to adjust whenever your plans change. I never touch my itinerary again once I'm done creating it, because I want to be focused on my travels when I'm on them. But I do always have a list of "extra" things I'd like to see that may not be built into that itinerary. This is great because if a place you want to visit closes early or a line at a restaurant is too long, you'll probably have other nearby options that you've already researched. Essentially, it's a wish list of extra things you'd like to try if you have the time. Like I said, plans change, so you might be surprised how things happen.
Bonus: Follow #InstagramInfluencers
This step might not be for everyone, but as someone who spends probably too much time on Instagram, I've found that it's also a very useful tool when it comes to planning trips. Most major cities have major "influencers" whose job it is to basically post photos around the city (a quick Google search will help you find them). And when it comes to planning a vacation, their accounts are very useful. Of course, it's best to follow lifestyle/travel influencers rather than those focused on fashion for obvious reasons. I almost always do this when I'm planning a trip somewhere. For example, when I was planning a trip to Disney World, I followed several Disney influencers (yes, it's a thing, and a really big thing) and got so many ideas of places to visit/park tips/outfit inspiration that I probably wouldn't have otherwise. The neat thing is that by following these people you don't have to actively seek out information. You'll just come across it as you're scrolling through your Instagram feed/stories. If you don't like following all those accounts, you can always unfollow once you get back from your trip.
Having written out this whole process, I realize it all seems a lot more complicated than it actually is. I do follow this process for my trips, but it's not as time consuming and burdensome as it might sound. Honestly, the planning process of trips is fun for me, because I learn so much by doing it. The tips you read in people's blogs and articles stay with you even if you don't add them to notes that you reference while traveling, and creating maps and itineraries helps you understand how a city is structured.
Planning like this also just helps you get the feel for a place. Seeing people's photos from when they traveled to that area helps you see what it might be like before you step off the plane. So really, the most valuable thing about being deliberate when planning your travels is what you get as you plan. It also makes me even more excited as I count the days down to my next trip. And I'm very much a fan of that feeling.
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