The Traveling Fool

How to Use AI Travel Planning for Memorable Trips

Bob Bales Season 5 Episode 39

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Dreaming of the perfect getaway but overwhelmed by endless planning details? You're not alone. The latest wave of travel innovation is here, and it's transforming how we discover, plan, and experience destinations around the world.

As I reveal in this episode, nearly 20% of millennials turned to artificial intelligence for trip planning in 2024 - and I'm among the growing number of travelers leveraging these powerful tools despite being decidedly outside the millennial demographic! Through extensive personal testing of platforms like ChatGPT, Grok, Google Bard, TripGenie and RoamAround, I've uncovered remarkable strategies that can save you hours of research while uncovering authentic experiences that most tourists miss completely.

Ready to transform your next adventure? Try these AI strategies for yourself, and share your experiences with me at thetravelingfool@yahoo.com – I'd love to hear how technology enhances your travels while keeping the human spirit of discovery alive!

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Bob:

Hi and welcome to the Traveling Fool, the show where we explore the most intriguing aspects of travel, culture and history. I'm your host, Bob Bales, and today we are talking about using artificial intelligence to plan a trip. I'm going to give you some tips on how to do it effectively, so stay tuned and we'll be right back.

Bob:

Picture this You're dreaming of a beach getaway, but planning feels well overwhelming. You're thinking about flights, hotels, sites that you want to visit, nearby restaurants and more. Then, in minutes, an AI tool spits out a five-day itinerary, complete with a hidden beach and a budget breakdown. Welcome to travel in 2025. Nearly 20% of millennials used AI for trip planning in 2024, and that's as per the travel industry reports and it's reshaping how we explore. Now I can tell you I'm not a millennial and I have used it. In fact, I use it a lot when I'm looking to go somewhere, and in this episode, I'm going to talk about how to craft a personalized trip. I'm going to cover some practical tips and how to use AI to our advantage, while keeping travel human. I've been testing AI tools for my own trips, like I said, and today I'm sharing what works and what doesn't. Ai tools like Chat GPT, grok, google Bard and travel apps like TripGenie and RoamAround. They're booming because they process massive amounts of data, flights, reviews, local events, and they do it all in seconds. Searches for AI travel planning have jumped 30% year over year, as per Google Trends, and that just reflects the demand for speed and personalization.

Bob:

So how does AI work? Well, it pulls from sources like Google Flights, yelp, travel blogs, podcasts. It pulls from everything out there that it can get its hands on, predicting preferences. In other words, if you like street food, it will build an itinerary like a three-day Hanoi trip to food stalls that you might want to visit and pagodas if you're interested in history. It saves hours, it uncovers all kinds of offbeat and out-of-the-way places and provides real-time updates for weather alerts, airfare, jobs, even things like security in the country. But it also has a few drawbacks, and that's what you've got to be careful of. You risk getting generic suggestions or missing the local nuances, such as AI overlooking a festival or telling you about one that doesn't even exist anymore due to outdated data. So while AI is a great tool for travel planning, you've always got to double-check stuff.

Bob:

So here are some examples on how to use AI to effectively plan your next trip. First, you can use it for generating a list of like offbeat destinations. I love visiting places where tourists don't go, I mean, or just don't know about. I like to discover those things and for years I've done it by just wandering around and finding them on my own. Well, you can use AI to discover lesser known destinations that match your interests, whether it's history, like I like, or libraries, or just solitude, nature or parks or whatever. You can use it to find those places instead of the touristy spots and the tools that you want to use. Now here's the thing AI's got a lot. There's a lot of different AI tools out there, so some of them are better than others, depending on what you're looking for.

Bob:

Now, if you're looking for like offbeat destinations or specific type things, the tools you want to use are ChatGPT or Google's BARD. They just seem to be better at it, and what you want to do is, when it comes up to the little square box that you put in the information that you're looking for, just like a Google search, it gives you a search block and you want to prompt it. You can put list 10 secluded US towns with historic sites and low tourist traffic. That's ideal for a solo traveler. Now that sounds good, right? You're like, oh yeah, not a lot of tourists traveling solo historic sites that's what I'm looking for, but you really need to be more specific. We're going to get into this a little bit later, but instead of just saying low tourist sites put in, I'm looking for a list of 10 secluded US towns with historic sites under 5,000 visitors annually that are ideal for a solo traveler. Cross-check your results with various sources out there just to make sure everything is right, and you're going to get a list of places that you may never have even heard of.

Bob:

Now, like I said, you can use AI for a lot of different things when it comes to travel planning. One of the things you can use it for is comparing flights across multiple platforms. Use AI and leverage it to aggregate and compare real-time flight deals from various booking sites. It saves you time and money. Some of the AI tools you can use which I've used are Kayak Kayak has an AI price check or Google Flights. All you have to do is put input flights from New York to Edinburgh, scotland, in June of 2025. Under $600. And put that into Google Flights. Ai scans Skyscanner, expedia and Airlines for deals. You can also set price alerts in Google Flights for AI-driven notifications on fare drops. And here's a tip Just book your flight sometime during the middle of the week and you'll usually save a little bit of money. But instead of sitting there searching every single website on your own, let AI do it for you and it'll kick back the results. Then you can go to the exact website you're looking for whether it's an airline website or whether it's one of the aggregators and buy your ticket. Saves you a lot of time and money.

Bob:

Now I don't know about you, but when I travel, I like to visit a lot of locally owned restaurants. I don't want to go to the big chain restaurant. Trust me, I love a great steak. Fancy steakhouses are great. I could go there a lot, but I like to visit those places that have been in town for 20, 30 years that the locals love, and I want to find out what's special about it. I've been to some great burger joints around the country, been in business for 30, 40 years, still in the same family, and they're busy, and when you get there and you try the food, you understand why. Well, I want to go to visit those places so you can use AI to find locally owned restaurants. The tools you want to use are Grok Now if you can't tell by my accent, that's G-R-O-K grok or perplexity. That's another AI tool that you can use. They're really good at this. So what you do is you put in there your prompt.

Bob:

Now I'm getting ready to head out on a trip to Abilene, kansas, and Hays, kansas, and some other places. I'm going to be gone for a while, so I wanted to find locally owned restaurants that maybe I could check out when I've got some time. So I put in a prompt find locally owned restaurants in Abilene, kansas, that have authentic Kansas barbecue, avoiding the tourist traps. Well, it spits out immediately the Hickok, and then it goes on to tell you it's a out immediately the Hickok. And then it goes on to tell you it's a newer addition to the Abilene dining scene. It opened in 2024. It specializes in Kansas-style barbecue.

Bob:

Now it also gives me menu ideas as well as prices. It tells me to get the brisket plate with apple slaw and jalapeno beans for $15, or go for the Branding Iron Burger, which is a quarter or a half pound patty. I don't know if I want this one, but it comes with peanut butter, bacon, jalapeno jelly $12 to $15. They say, don't forget to get the million dollar bacon. I do love bacon, Thick cut and sweet spicy appetizer for $6. Tells you the estimated cost for eating. There is between $15 to $25 per person, and it goes on. Just a whole lot of other stuff.

Bob:

Now, if you don't want that, I'll put back in there. Well, find me locally owned restaurants in Abilene, kansas, that have been in business for at least 20 years, avoiding the tourist traps. And immediately it gives me Joe Snuffy's old-fashioned grill. We're talking about kind of place. Now, again, it gives me Joe Snuffy's Old Fashioned Grill. We're talking about kind of place. Now, again, it gives me menu ideas with prices, tips on the best time to visit, why it's popular, and just a whole bunch of other stuff. Another one that kicks out is Amanda's Bakery and Bistro. Okay has the same type of information. So immediately I mean I'm talking within 30 seconds you put the criteria you want in there and it will spit out some suggestions for you to check out. Now here's a tip that you can use when you're putting your little search in there Ask for restaurants that have high local reviews on Yelp or TripAdvisor or Google.

Bob:

Another example how to create a budget breakdown you can use AI to estimate your trip costs, flights, lodging, activities based on your budget and the destination you're going to. The tools you might want to use for this one are ChatGPT or Copilot. They're great at doing this. For the prompt that you want to search for, just tell it.

Bob:

Estimate a seven-day solo trip or family trip or trip with two kids, whatever it is. Estimate a seven-day solo trip budget to Edinburgh, scotland, including flights from Chicago, budget, lodging and historic site visits for under $1,500. And you're going to get the whole shebang. It's going to kick out all kinds of stuff. This is what you need to spend for flights. This is how you're going to some ideas for hotels and this is what they're going to cost. This is what entry fees are going to run. This is what public transportation is going to cost you when you get there. Here's some tips on where to buy cards to get you the best deals for the public transportation.

Bob:

It's going to kick out just a ton of information and you can request a breakdown by category. I want it broken down by transportation how much food is going to cost? And you can request a breakdown by category. I want it broken down by transportation how much food is going to cost? And you can compare that with other sites just to see if you're in the ballpark. Compare it with places like Expedia. They have a cost estimator for accuracy. Now you got to remember this is not perfect. Ai is not your travel agent yet who knows what's going to happen in a few years? But it's going to get you a ton of information that is very close to being extremely, extremely accurate and perfect. So you still have to check things. You have to double-check budgets with things like Expedia's cost estimator, or you have to check, okay, is this festival still going wrong? But it's going to get you everything that you need, which brings us to another example.

Bob:

You can discover the hidden cultural events that go on, things like local festivals or events that are not listed in mainstream guides. You know, I love going to places where they have some kind of local thing going on, because you just get to meet everybody, especially when I go overseas. I mean, I love traveling to USA, don't get me wrong. There's places in this country that are absolutely fantastic and the people are great and I had a blast, but I don't know, man, it's just something about going to a foreign country and getting immersed into their culture.

Bob:

Well, if you're looking for hidden cultural events, the tools that you want to use are Google's BARD or Perplexity, and I got to tell you, though, when I'm giving you these suggestions for these AI tools, I would almost always put Grok in there as one of the standbys, because it searches a lot of the AI tools when you're doing this thing, but you want to put a prop in there when you're looking for cultural events, and what you want to put in there for the search block is we'll stay with the Scotland theme. I don't know why. I've never been to Scotland, but I've wanted to visit for a while. Find small cultural festivals in Scotland for June of 2025, small cultural festivals in Scotland for June of 2025, like music or folklore events that have low tourist attendance. I don't want to go to a festival that's being put on by a bunch of tourists. I want to go to local festivals and you can even add that some more in there that are in smaller towns, and then you just cross-check that event details with the local tourism site. You can go to visitscotlandcom or you can go to the local town tourism site and just double-check Okay, is this event still going on? Oh, no, it was wrong. They moved it a week. Okay, well, I know they'll be there the following week. So you just take the information it gives you and double check it with the local websites. So here's another example.

Bob:

You can optimize public transportation routes. I don't use public transportation in Texas. It's just not practical. I mean driving in a vehicle. It takes you, oh Lord, an hour and a half, two hours to get across town. Sometimes, where I live in Houston, some cities in the United States have great public transportation. Houston doesn't. It's just flat, not practical. But overseas, in foreign countries, public transportation is great and I've used it tons of times. Well, ai can plan an efficient bus or train route for car-free travels. It'll save you time and money.

Bob:

The things you want to use for the public transportation routes are Google Maps with AI routing. Or there's this website called Rome, the number two, rio, rome to Rio. It tells you how to get from one place to another. So you can enter Edinburgh to St Andrews by train or bus June of 2025. Put that in the Rome to Rio site or Google Maps and it'll tell you all kinds of info, but it'll suggest how to do it the best. It'll tell you to go to Scott Trains or Scott Rail Trains. It's a one-hour trip, it costs $15, and it gives you the schedules. Or you can use Google Maps and use the Explorer function on the Google Maps. It's a feature and it'll give you real-time transit updates. Buy your tickets early via train line and you get even more money off. And it tells you all this. When you're doing these searches on AI, it'll give you very detailed explanations of where to get the best prices, best times to travel and just all kinds of stuff. So, just be detailed when you enter the information in there and, trust me, you're going to save time and money.

Bob:

All right, when you're traveling, you want to take a lot of photos, right? Well, I do. And then you've got the Instagram warriors out there who want to get the perfect shot. You know, standing by the waterfall or whatever, I don't know. Everybody's a photographer with phones these days, because the cameras in the phones are great and you want to show off those photos. Well, ai can give you some great shot suggestions. It'll suggest the best locations and the time of day for your photos, whether it's early morning, interest, or it tailors it to all these destinations and for this, use chat, gpt or Grok. Here's what you want to put in the search block Give me a list of five early morning photography spots in Edinburgh for sunrise shots, including the viewpoints and the landmarks, and it will just spit out very detailed instructions on where to get that perfect photo from. And you don't have to. I mean, you got your own personal photography assistant right at your fingertips. You can put in there. Give me a list of five shots that I can take in the evening to get that perfect scenic view of the city, and it's going to spit it out. Verify spots that it gives you by going to places like Instagram or Flickr, which is a big site that people use to store their photos, and you can go through there and look at everybody's photos. Or you just do a Google image search and look for shots like that and you can see what others have done. You go oh yeah, I want to get something like this. So use AI to give you those suggestions of the locations, the times of where to get these great photography shots.

Bob:

Another example you can identify unique lodging options If you don't want to stay at the big chain hotels or you want to stay somewhere that you can tell somebody about. I mean, I've been to a lot of places and rarely do I come home and go. I just stayed at the most fantastic Ramada Hotel. You never tell that story. You tell about the places you've been. However, you might tell somebody if you stayed at a haunted hotel or a really cool bed and breakfast or some kind of place that's just not your average place. Well, you can use AI to find these quirky or historic accommodations, like I don't know, the Driscoll Hotel in Austin or Gold Hill Hotel, which I stayed at in Nevada the oldest hotel in Nevada. It was just cool. Those are the hotels that you remember. So you can use it to find haunted inns or whatever you're looking for to give you a memorable stay.

Bob:

The tools you want to use for this are Perplexity or Copilot. Now, when I'm giving you these suggestions on which tool to use, you can use any of them, but those two or the ones I give you for each scenario, those seem to work better and give you different options, and they just work better for various scenarios. So Perplexity or Copilot are the best to use when you're looking for unique lodging and you can put it there find unique, historic lodging in Abilene, kansas, like Haunted Bread Breakfast or a Victorian Inn, with rates under $150 a night. I did that and put it into perplexity. Automatically it pops out Abilene's Victorian Inn Bread and Breakfast historic lodging experience. It gives me a map. It tells me where to get to it. It tells you a little bit about its home of somebody named Swede Haslett, who was President Eisenhower's lifelong friend. It gives you all kinds of information about it. Also tells me about a place called Ingle House Bed and Breakfast which is on the National Register of Historic Places. It's a home, Spanish Colonial house that was built in 1926 by the founder of United Telephone. It tells you about the property, where it's located and why it's perfect for travelers who want a self-catered experience in a unique setting in a unique setting.

Bob:

So AI can spit out these places that you might not find if you're going to booking dot com to look for a place to stay. But all you have to do is, when it gives you the information, like I said with all of the examples I'm giving you, you just want to cross-check it with other resources. So with lodging, you just want to cross-check it with Airbnb. Look up the specific thing it's telling you, or go to booking dot com or expedia dot com and just check to see what the availability is, read the guest reviews and check out the guest reviews on TripAdvisor or Google or Yelp or whatever to see how the property stacks up.

Bob:

Ai can even give you some things. Especially if you're traveling internationally, you might want to learn a few phrases such as where's bathroom or where's the police station. No, I mean, you want to learn a few local phrases to help you get by. So AI translation tools can help you learn key phrases that will help you connect with locals and enhance your experience while you're there. For these, you use Google Translate or there's another site called Deep L, the letter L, d-e-e-p-l, and you just input Scottish Gaelic phrases for greeting locals and it will kick out what it is, along with the pronunciation and how to do it.

Bob:

Practice phrases via Google's Translate Audio feature and just ask the locals why you're there. Hey, did I say that? Right? And they're like no, you were asking for a purple umbrella, whatever it is, but I have learned it was. When you travel overseas, if you know one or two words in the local language, they seem to just really appreciate it more. Hey, this guy is. You know he said it like an idiot, but he's tried, for whatever reason it seems to open up a lot more avenues of things, simple things like good morning, hello, thank you, various little terms and terminology that you can use, no matter where you're traveling to. Whether it's Scotland, germany, hong Kong, tokyo, doesn't matter. Just learn a few phrases. Ai can teach you how to do it. It'll make your trip a whole lot better.

Bob:

Now here's another one, a great example, but this one you definitely definitely need to double check on. You can research visa and entry requirements. It'll just quickly spit out visa rules, health requirements, travel advisories for your destination. Use Grok or Google's BARD, and it can be simple searches like what are the visa and vaccination requirements for a US citizen traveling to Thailand in June of 2025? It's going to kick out the information real quick. It's going to say you need a visa. You can get it upon arrival. It's good for so many days. If you need any kind of vaccinations which, if I remember correctly when I went, I didn't need any It'll just kick it all out.

Bob:

Here's the thing. You need to go to other sites and double check it, especially with these visa requirements. Things change and you verify the response you're getting with the official sites such as travelstategov, the US's travel site, or go to the country's embassy and check it for accuracy. Us has embassies from everywhere and just look up thai embassy or consulate and just double check it. But for just initial searching and quick referencing. It's great you say you know I've always wanted to go to bali. I keep seeing the beautiful photos of it. I'd like to go there before the tourists ruin it totally. Well, just type in their visa and travel requirements for us citizens traveling to bali in december of 2025 and it's going to kick it out and you go. Huh, my passport needs to be valid for at least six months after I arrive. I don't know if it is Okay. Maybe I ought to get a new passport before I do anything else. So it's going to give you the quick information and then you can just double-check it with the official country's websites.

Bob:

Here's another one Find secluded beaches or natural sites. It can pinpoint remote, low-traffic beaches for parks or whatever for solitude. Use chat, gpt or perplexity. Again, just simple searches. List five secluded sandy beaches in Florida that get minimal visitors, accessible by public transportation, and you can get specific. You know that various access details that I have to hike to get to or that I can park close by, or and just check crowd levels from other sources. We're going to start going through the rest of these a little quick.

Bob:

Another example generate packing tips for specific trips. It can create a tailored packing list based on the destination, the weather, the activities, ensuring that you are prepared for where you're going. Certain parts of Asia if you go during certain times of the year, you're in monsoon season. Certain parts of Europe get very cold in the wintertime. So it can create a great packing list for your trip using Copilot or ChatGPT, simple prompt again Create a packing list for a seven-day solo trip to Scotland in June of 2025, including photography gear and rain protection, and it's going to kick out a list. You can even ask for specific weather items like what is the weather normally like in June? What are the temperatures like? It's going to give you these lists so you might want to pack a light coat if you're going to be there in September or October. Oh, I didn't know, it got down that cold that early. So just use it for general or very general type packing lists.

Bob:

Here's another example you can analyze traveler reviews for insights about the places you're going to. It can summarize reviews for hotels, restaurants or attractions to identify authentic, locally favored spots. Those you want to use are Perplexity or Grok, and you can just simply summarize, put in there. Summarize TripAdvisor reviews for locally owned restaurants in Edinburgh highlighting non-touristy options, or summarize TripAdvisor, yelp and Google reviews. Put all three of them in there and just cross-reference it for yourself. Go to a couple of these sites and check them out.

Bob:

You can use AI to plan accessible travel for specific needs. I'm an old retired army guy. My knees are shot. I don't like going up steep hills or having to climb a lot of stuff. Going up and down hills or steep inclines tears my knees up to the point I can barely walk. So you can put it. Or you've got relatives or family members that might be on crutches because they hurt a foot or might be in a wheelchair or whatever. Well, ai can find specific accessible attractions, lodging or transportation that will include travel for specific needs.

Bob:

Use AI tools like Google's BARD or ChatGPT and it can be a simple list of wheelchair-accessible historic sites and hotels in Edinburgh for Solo Traveler in June of 2025. And it's going to kick out the hotels that have accessible features and historic sites that are easy to get to. It's not going to tell you about the castle that you've got to climb up a hill to get to and there's nothing but all these steps and stuff. Instead, it's going to give you very detailed things and you can even put a little more search information in there. Very detailed things and you can even put a little more search information in there. Request detailed accessibility info, like places that have ramps, elevators, and then just confirm it with the venue before you go. Just double-check it. If you go into a historic site, they've all got emails. Just shoot them an email.

Bob:

So, that's a lot of information that AI can give you for planning your trip. So what's it look like in the future? Lord knows, but they are anticipating that by 2030, ai could integrate with augmented reality, letting you walk a destination virtually before you ever get there. And I don't know, man. Is it a good thing? Is it a bad thing? Will AI make travel too robotic? You know there's something to be said about stumbling upon a street party in a place you're visiting and the intimacy of just finding things on your own and exploring. So I guess the thing you want to do is use AI as a guide and not the end-all tools for everything.

Bob:

And here's the key when doing an AI search for trip planning, instead of typing in, give me a five-day itinerary for visiting London, type in a very detailed question based on your interests, and I'm going to give you an example. When I do a search and I'm looking for an itinerary or specific things in this thing, in this example, I'm going to give you an itinerary. I get very detailed and you can even get more detailed than what I go into here. But here's something that I would typically search for. I am visiting London for the first time and will be traveling solo. I will be arriving by plane at Heathrow Airport on a Tuesday in the morning and departing the following Monday in the early evening. I want to visit historic locations out of the way, interesting things that don't see a lot of tourists. I want to try restaurants and pubs where the locals go and not the tourists. I want to stay in a modest, priced hotel in a convenient part of the city where I can take advantage of public transportation, gift me a detailed itinerary along with hotel suggestions on how to effectively use public transportation without me having to be rushed but taking time to enjoy the city.

Bob:

Now I put that exact search into a couple of sites. It took all of 30 seconds before it started spitting out tons of information it was giving me. It gave me three specific hotels, told me what the price ranges were, told me why those hotels fit my criteria, where they were located in the city, how close they were to public transportation hubs. It gave me suggestions on where to eat, why it was popular with the locals, why tourists don't go there. They just don't know about it.

Bob:

All kinds of little, out-of-the-way historic locations. It didn't spit out the big ones, because when I went in there and did a search I said I want interesting places that tourists don't visit. So it didn't give me Buckingham Palace and the Horse Guards and Westminster Abbey. None of them. Westminster Abbey, none of them. It spit out a ton of other places, like the Freud Museum and from Sigmund Freud and just all kinds of little, obscure and unknown little places that I had never heard of.

Bob:

That those are the places you want to visit. Well, I do anyway. Yeah, I want to visit the hot spots, but I want to visit those little out-of-the-way places that people just don't know about. So get very detailed when you're doing these searches and you'll get a lot of information.

Bob:

So here's the deal. Ai saves you time. You can personalize your trip. It'll find all kinds of little hidden gems, but it'll pair it with human curiosity, for, you know, authentic adventures. Next time you're getting ready to go somewhere, try an AI tool for your next trip and just shoot me an email at thetravelingfool at yahoocom, or editor at thetravelingfoolcom. Let me know how it goes for you. Tell me what you found out, what you liked about it, didn't like about it. Maybe I'll talk about it on a future episode, but that's it for this week's episode. I really appreciate you listening. If you like the podcast, hit the like button, do me a favor, email it to somebody and share it with them. Maybe they'll like it too. And until next time, well, safe travels, thank you.

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