Is My Trip Planning Process Outdated? I Tried a New Tool

A hidden treehouse in the Amazon, what to know about the jet fuel crisis, and an easier way to plan your next trip.

This article was sponsored by Adobe. As always, all opinions and ideas are entirely my own.

Every trip starts with a spreadsheet. For the last decade, the second I’ve conceptualized an idea, I’ve typed “sheet.new” into my browser and diligently started inputting inspiration: Dates, airports, budgets. By the time my husband and I leave for a trip, I have one Sheets document, separated into tabs; a living, breathing resource we refer to for our daily plans.

In some ways, I feel behind the times, like I’m doing manual work that could be automated. When everyone’s using AI and social media for their trip ideas, I’m more old school, looking for off-the-beaten-path ideas, the slow travel way—a fact I’m deeply proud of.

Most recently, though, our three-week trip to China and Taiwan—a plan that required understanding 240-hour transit visas, flights for both work and leisure, and an entire suite of apps necessary to navigate the Great Firewall and China’s payment systems—was a beast I needed more support with. As I’ve alluded to previously, I’ve never needed to plan for travel the way I did here.

Coincidentally, around the same time that I started planning in the fall, Adobe’s team reached out wanting to showcase a new Adobe Acrobat feature, PDF Spaces. (An aside: As a former teenager who spent hours after school teaching herself Photoshop for Xanga headers, to a professional who uses Premiere daily for work and Lightroom for film photography touch-ups, hearing from Adobe was truly a pinch-me moment.)

PDF Spaces is an AI-powered online workspace that aggregates and synthesizes your files, documents and web links in one place. For someone like me with a thousand tabs open at all times (something my friends and coworkers endlessly rib me about), this felt like a lifesaver. By the time I got off the call with Adobe’s demo team, I was sufficiently impressed with its capabilities, but I wanted to know: Could PDF Spaces actually be a better option for planning than my tried-and-true method? So, I decided to try it out for comparison.

Before I go any further, I want to clarify: One of my largest hesitations around AI is generative AI—from an ethical standpoint as a writer (em-dashes forever; I’ll never forgive AI for that), and from the climate change POV as an environmental advocate. Trawling the entire Internet and requesting curated itineraries may seem like a quick ‘n easy solution for individuals, but it comes with a real cost. Here, however, you’ll find that this process is contained in a closed-loop system—one I’ll share more about shortly, but ultimately one I felt much more comfortable with.

So, (Nathan for You voice:) the plan? Build my own itinerary by hand as usual, and also on PDF Spaces, to see if this would be a more efficient method and a worthwhile tool for future trips.

First, I created my Google Sheet as normal: A tab each for our overall schedule, our expenses, and a packing list. Because my husband was primarily flying to Shanghai for work, I knew the first week would be spent in that area, and I started inputting his flight information while I researched my own options (cash, points, or a mix of both). I ultimately ended up doing points at a very steep price, but I’ll be sharing those expenses in a separate post—stay tuned.

Then, we had effectively 10 more days we wanted to travel around, before returning to work in the States. As we debated splitting our time between Hong Kong, Taipei, Seoul, or Tokyo, the prices around cherry blossom season in South Korea and Japan were exorbitant. Relatedly, I’d heard a lot over the last few months around Taiwan as a rising destination. Rather than spend 10 days entirely in Taiwan, we decided to split that time between Hong Kong and Taipei, as a friend recommended.

For this part of the planning, I found myself continuing to rely on my spreadsheet. It was especially helpful for mapping out the possibilities of how many days to spend in each location, which hotels we wanted to stay at, and organizing miscellaneous expenses, in one central place.

Then came the question of: What do we actually want to do in each city? Many of our friends had been to Hong Kong, but fewer had been to Shanghai or Taipei, so it required a bit more digging around. The challenge I often run into though, as someone who doesn’t like using viral videos and AEO-generated results for recommendations, is that I’m often overwhelmed with what’s out there. There were dozens of “What We Did in Shanghai” posts to consider, and most of them were not really tailored to a slower form of travel. (Many recommended hitting five or six sights in one day, which didn’t seem realistic or honestly engaging for my type of trip.)

Well, I did what any resourceful millennial would do: I asked for recs on Instagram and here on Departure. Both friends and strangers came through with lots of useful tips and tricks, and then I was able to leverage PDF Spaces to synthesize them all for me.

screenshot from Notes within PDF Spaces

Regarding that aforementioned closed-loop system: What I specifically appreciate about PDF Spaces is that the tool only aggregates and analyzes the data you put into it; in other words, it’s not searching the entire World Wide Web for what to pull in, only what you upload. That also helps me avoid the dreaded AI slop I often see online when folks use AI chatbots, where travelers are sent to destinations that don’t even exist, or contribute to overtourism by heedlessly heading to popular destinations from generative AI’s recommendations.

In my case, with permission, I compiled texts of what friends recommended, screenshotted entire conversations from WhatsApp and Instagram (I first made them readable PDFs, but you could just copy/paste the text separately), downloaded Google Map highlights, webpages of recommendations, and saved PDFs of articles with worthwhile suggestions. In each PDF Space—one for China, and another for Taiwan—I uploaded all the files.

Then I created the prompt: “Please create an itinerary for our time using these sources. We will have three days available in early April, from Sunday April 5 to Tuesday April 7.” To make this easier, you could also customize the Assistant by creating a “Travel Guide” and giving it instructions such as, “You are a travel guide that is helping me maximize my time in China.”

Within seconds, I had a day-by-day breakdown of what to do based on the recommendations I had compiled, without having to read through them all on my own and seeing what came up repeatedly as worth visiting.

At the bottom of each itinerary, there were also “additional notes” to keep in mind: Recommended transportation around the city, or the weather to consider—notes that came from friends, but that were easily shared here. Planning for several weeks of travel immediately seemed more manageable, and every rec came with a citation of where it internally pulled that data from so I could go back and reference the source of the original suggestion.

Once you’ve reviewed your itinerary and finalized any files you want to upload, you can save your prompt section as a “Note” for easy access. This was helpful, because it loaded fairly quickly without needing a ton of data, and especially since we were in China, it worked seamlessly with our VPN. If you’re nervous about not having any roaming data or WiFi at all, you could also download your Note directly as a PDF or Word Doc to have on hand to reference.

Another feature in PDF Spaces I personally liked is that you can share it, so other travelers can add information as well—a must-have if you’re carrying the mental load of planning a trip and want to spread the effort. Not speaking from personal experience or anything. 😉 Other scenarios could be a joint bachelorette party you’re planning with other bridesmaids, or a family trip with multiple generations who want to try different activities. The collaboration feature is a great way for everyone to pull their own weight.

I did run into a few things worth keeping in mind as you use PDF Spaces. Since it works based on what you upload and supports specific file types, certain content—like an Instagram Reel—can’t be directly pulled in. In my case, I watched the Reel, noted the recommendations, and uploaded the text instead, which worked well as a workaround.

Similarly, while PDF Spaces can break down a daily itinerary, it doesn’t automatically account for things like specific dates aligning with days of the week. It’s helpful to do a quick pass to double-check details like hours and availability as part of the final polish process.

As with any AI tool (especially with any AI tool?), you’ll definitely need to go over your plans with a fine-tooth comb instead of assuming you’re good to go…and that’s where my old trusted method of manual research came back into play. (In my case, the tool wasn’t aware that April 7th was a Tuesday, so there is some fact-checking along the way that you’ll need to verify.) I’d say this tool saved me several hours of time, though.

Overall, while I still plan to keep a main document for trips, I really liked how effortless it was to use PDF Spaces for day-by-day plans: If you’re someone like me who wants to amass as much information as possible and make the most informed decisions and itinerary you can, I think this tool will reduce most of the heavy lifting for you.

You could also take the next step and upload all your flight confirmations, hotels, etc. and get a detailed hour-by-hour schedule—down to your check-in time—which can be useful if you’re already on the go and just need a simple answer, without going back through dozens of emails. Another moment of speaking from experience. 👀

If you already use Adobe’s product suite for other reasons, PDF Spaces might be included in your subscription; otherwise, plans start at $24.99/monthly as part of Acrobat Studio, which is the complete set of PDF tools, Acrobat AI Assistant, Adobe Express Premium and PDF Spaces, or you can test out a free trial here. Ultimately, I do think it will be hard to go back to my manual approach alone, so I’m hoping to continue using these two tools in tandem—an effective way to make travel planning smarter, not harder.

• ⛽️ What do travelers heading to Europe need to know about the jet fuel crisis? Talking Points with TPG’s Brian Kelly has three tips to keep in mind (and I agree with all of them). Please protect yourself.

• 🩹 I had a hidradenitis suppurativa (HS) flare-up while traveling over the last month, and I’m extra grateful I had a mini-first aid kit on me to deal with the mess. (I’ll spare you the details.) Travel first aid kits are often just $2–$3 and worth bringing along.

• 🌴 File this under “a dream getaway one day if I can afford it:” a hidden treehouse nestled inside the Peruvian Amazon rainforest. Prices start at $1,490/night for two people which is currently outside of my budget, but wow, is it stunning.

• 😇 New quarter, new AmEx Platinum benefits, particularly the $75 lululemon credit. I’m not a huge fan of their excess production, but for the sake of using the credit (or for an early Mother’s Day gift), these would be my travel picks (affiliates): This fitted jacket, this foldable crossbody, or this dual-compartment toiletry bag.

• 📚 At the intersection of everything I love: The Travel Book Club on Substack. Author Oyinkan Braithwaite of Cursed Daughters and My Sister, the Serial Killer even joined their latest book club meeting.

Soon, I’ll break down everything on where we stayed, spent, and ate over our nearly three weeks in Shanghai, Hong Kong, and Taipei. If you have any questions about China or Taiwan, let me know and I’ll try to answer them as well. — Henah x

weekend mood in hong kong // credit: cecelia chang