Using AI to Plan a Trip? Don’t Make These Mistakes

This Week

I’m heading to Italy this fall, and planning the trip turned into a bit of an experiment: 

What happens when you use AI to plan a real vacation?

I tested out travel apps, booked insurance through an AI-powered platform, and talked to travel advisors about how this technology is changing the way they work, from trip design to backend operations.

Some of the tools were genuinely helpful. Others made me wonder how many people are showing up to closed restaurants or missing key travel documents.

This week’s newsletter is all about travel. The tools I found most helpful, tips for using them well, and what the pros want you to know before you let a bot plan your vacation.

What you’ll find in this issue:
→ Can you trust AI to plan your vacation?
→ The 5 best AI tools for planning a trip
→ How to create a custom packing list with AI
→ A video walkthrough of how I cut my video editing time in half
→ Why AI strategy has more to do with people than platforms

Let’s get into it.

Can You Really Trust AI to Plan Your Vacation?

At a recent workshop, I asked a group what they were using AI for most often. The top answer wasn’t writing content or building workflows—it was planning a vacation.

That answer surprised me because I’ve heard more than a few travel-gone-wrong stories lately. 

People showing up to the wrong hotel, booking dinners at restaurants that shut down years ago, or missing key documentation because ChatGPT didn’t flag the latest visa requirement.

So I reached out to a few travel professionals to get their take. Were they worried that AI tools might replace them? 

Not at all.

Courtnie Nichols, founder of Biz Huddle, put it simply:

She’s seen travelers rely on AI for bookings that didn’t match their style or their schedule and there’s no one to call when things go sideways.

Belvin Baldwin III from Showtime Travel has seen the same thing:

The bigger issue is that AI doesn’t know your preferences, priorities, or the little things that can make or break a trip. Like whether you need a hotel with blackout curtains, or that the museum you’re dying to visit is closed on Tuesdays.

Emily Miller from Lark Song Travel ran a test and asked ChatGPT to create a sample 10-day Italy itinerary. The result was a rough draft at best.

And that’s the core of it: AI can help you brainstorm, but it can’t personalize. It doesn’t know what you don’t know, and in travel, that can cost you time, money, and an enjoyable experience.

That’s where human travel agents and advisors shine. They bring their own experience, local knowledge, and a sixth sense for spotting what’s missing. They make sure your trip runs smoothly, even when things change last-minute.

So no, AI can’t replace a great travel advisor, but in the right hands, AI can make them more effective.

Advisors like Emily are using AI to draft marketing materials, write hotel description and convert supplier proposals. Courtnie built a chatbot trained on her entire knowledge base so it could answer client questions and give her the space to work on more important projects. 

Patricia Zest of Exemplary Travel Advisors, introduced a work flow at her agency that compiles commissions into easily readable statements for each advisor and keeps an ongoing spreadsheet of production, by agent, for her agency. 

Michelle Denogean, CMO at MindTrip, said it best:

Technology can spark ideas, but it takes a real person to turn those ideas into a trip worth remembering.

Have you tried using AI to plan a trip?

Reply and tell me what worked… and what went totally off the rails.

5 AI Tools That Make Trips Cheaper, Easier & Way More Fun

AI won’t replace a great travel advisor, but it can help with all the moments between booking, boarding and coming back home. Whether you're trying to save money, decode a menu, or make smarter choices mid-trip, these tools can help.

1. MindTrip

This is one of my favorite apps for getting a feel for a destination. You can plug in your interests (wine, history, hiking) and it’ll serve up ideas, itineraries, and curated activities that match your vibe. 

I use it to get a lay of the land and start mapping out possibilities. You can book some hotels and attractions directly in the app, and for everything else, it links you out to the provider’s site.

It’s also packed with helpful features: You can browse 40,000+ travel guides created by real people, invite friends to collaborate, upload receipts to stay organized, and even extract recommendations from social posts or articles you find online.

On the ground, the mobile app is great for exploring what’s nearby, pulling up your itinerary, or using the Magic Camera to translate signs, menus or just snap a photo of something interesting and find out what it is.

Check it out at MindTrip.

2. Gondola.ai

If you ever book hotels using points, bookmark this one.

Gondola.ai connects to your loyalty accounts and tells you whether to book with cash or points—whichever gives you better value. It pulls in real-time pricing, compares redemption value, and even shows you hidden deals.

You’ll need to link your accounts to get the full experience, but it’s 100% worth it if you care about maximizing rewards. It also gives you cashback for booking direct, which most OTA sites won’t.

Visit gondola.ai.

3. Faye 

I signed up for Faye ahead of my trip this fall and the onboarding process was seamless.

Everything’s stored in the app, including my policy details, emergency numbers, medical resources, and even a currency converter. You can also access eSIM providers directly from the app, which is a nice bonus when traveling internationally.

I haven’t had to file a claim (and hope I don’t!) but Faye gets strong reviews for its customer service and speed of reimbursement.

You can sign up here at the Faye website

4. Hopper’s Price Prediction Tool

Hopper uses machine learning to predict if a fare is likely to drop or if you should lock it in now. It looks at historical prices, booking patterns, and demand signals to help you avoid overpaying.

You can also set alerts and get notified the moment prices drop for your route. If you’re flexible you can usually get a pretty good discount.

Access Hopper’s price predictor here.

5. Google Translate

Still one of the most useful apps to have on hand in a foreign country. After downloading the app, you choose your language, and then it’s plug-and-play.

You can use the camera to translate signs, menus, and packaging, or open the conversation tab to speak back and forth with someone. It is a little stilted, but it’s miles better than staring blankly at a menu or miming directions to the pharmacy.

Download the app for free here.

AI Just Upgrade my Packing Game

I’ve used the same packing checklist for years. It gets the job done, but it’s not exactly smart.

Then I saw a video from Desmond Wong where he used ChatGPT to generate a custom packing list and I had to give it a go.

For my upcoming trip, I gave ChatGPT the destination, time of year, what I’ll be doing (4 days of conference outfits + 2 weeks of vacation), a few wardrobe staples I wanted to include, and even my preferred color palette.

It checked the weather, built out mix-and-match outfits and gave me a full list tailored to my trip and my suitcase size (carry-on only).

Now we’ll see if I can zip it all up, but this beats my old static checklist by a mile.

Want the prompt to try this for yourself? Here you go:

“Help me pack for an upcoming trip to [LOCATION] on [DATES]. Create a packing list that fits in [SUITCASE SIZE] and includes all the essentials and outfit selections based on my color palette preferences [COLORS]. I will be [ACTIVITY/EVENT]. Create a check list I can reference when packing.”

And if you want to get extra fancy, you can even load up a few photos from your wardrobe and ask ChatGPT to select from what’s available.

Happy packing!

How to Cut Your Video Editing Time in Half

Do you find yourself with hours of vacation footage and no time at all to edit it? Then this videos is for you!

In this quick walkthrough, I show you how I use Descript, my favorite AI-powered video tool, to streamline the entire process. From drafting to editing to polishing, Descript handles a lot of the finicky editing so you can focus on the big picture (or video in this case!)

I show you:

• The AI features that clean up your audio and video in seconds

• How to generate B-roll automatically 

• The fastest way to create social-ready content without leaving the platform

If you’ve been dragging your feet on video, this will change things.

🎥 Watch the video on my YouTube Channel.

AI Starts with People, Not Platforms

I joined the Huddles podcast for a quick, no-fluff conversation on how CMOs can lead smarter GenAI adoption.

Tools matter, but what really moves the needle is trust, training, and a willingness to rethink how teams work. That includes getting leaders behind the keyboard, building in change management from the start, and shifting the focus from hype to hands-on learning.

Liza Adams and I talked about the most common pitfalls we see, like rushing to launch without bringing the team along, or focusing too heavily on outputs before investing in prompts, partners, and process.

We also shared examples from the field, including how one team collapsed a six-week video workflow into just two with the right mix of AI and people.

In this episode:
• What drives adoption (hint: it’s not automation)
• The difference between using tools and building skills
• What to track when making the case for GenAI investment

🎧 Listen here: Renegade Marketers

🎥 Watch here: YouTube

Want to Level Up Your AI Game?

If your team is ready for a hands-on AI strategy session, my custom-designed workshops are built to uncover the workflows that can save you hours every week.

Prefer to start small? My YouTube channel is packed with quick, practical “how-to” videos that show you exactly how I use AI tools for marketing, content, and automation.

Planning an event or conference? I deliver high-energy AI sessions that engage audiences and leave them with actionable strategies they’ll talk about long after the event. Book me for your event here.