Using ChatGPT as Your Own Personal Sommelier

How AI helped me discover local wines across Italy and why it made me a more adventurous wine traveler

Over the course of a little more than two weeks, I traveled from Venice to Rome, visiting several regions across Italy. While it wasn’t specifically a wine trip, I made it my mission to drink local wines everywhere I went. I never imagined that one of my most valuable travel companions would be ChatGPT. I certainly didn’t set out to test artificial intelligence while ordering wine. The idea happened by accident.

Venice

The first city I visited with a tour group was Venice, and on a night for dinner on our own, our tour manager suggested a restaurant for dinner that paired cicchetti (tapas) with local Venetian wines and cuisine. I’m always up for an adventure, so I found the restaurant Osteria al Cicheto. The restaurant doesn’t have many tables, and since I was alone, I sat at the bar. While seated at the bar, I noticed a sign that said: “Our tavern offers high-quality local wine. This means they have unique characteristics and a different taste than any store-bought wine…”

I discovered that was true because the tasting menu was a chalkboard in front of me filled with unfamiliar grape varieties, regional names, and Italian descriptions. It was divided into three sections: sparkling, white, and red wines. The different cicchetti were displayed next to me, and realizing it wasn’t going to be much food, I opted to select three wines, one from each category, to go with three different pairings.

I could see the food already on plates, so that was fairly easy to decide. The wines were a different story. I could have played it safe and ordered something familiar, but since I was in a different country and the restaurant served local wines, it was the perfect time to try something new. I started with the sparkling wines and tried to decide on a wine. I could identify some grape names and types of wine like Prosecco, but then it became a challenge since it was in Italian. I pulled out my phone and started doing my usual research by googling the name of the wine. Sometimes I found information on a particular wine, but often I came up empty. There were only three sparkling wines, and with a little help from the server, I eventually selected the 2022 Revi Trentodoc Dosaggio Zero. She also helped me select the best food pairing, which was blue cheese and pickled onions on some bread.

When it came to the white wines, there were seven of them to select from. I started googling again, and by the time I reached the third, she was wondering which white wine I wanted. I didn’t want to have her go through every wine again, so I told her to select something local that I perhaps hadn’t had before. She said the 2023 Davide Vignato “Orso Saggio” made with the Durello grape was good. I took her recommendation, and she selected tomato and anchovies on bread pairing.

While enjoying the white wine pairing made from a grape that I hadn’t had before, I looked at the chalkboard, trying to determine the red wine. There were five wines to select from, and I wanted to make somewhat of my own selection. Since the server and the owner were walking in front of the chalkboard all the time, I took a photo of the chalkboard so I could look at it more easily on my phone.

I looked at my photo of the chalkboard, and I’m not sure why I thought of it, but I had uploaded photos previously to ChatGPT, and it just clicked. I uploaded the photo to the ChatGPT app and asked the simple prompt: “Tell me about the red wines listed here so I can decide which one to get.”

That one question changed the way I approached wine for the rest of my trip.

Almost immediately, ChatGPT returned a list of the five wines along with bulleted descriptions of each wine. It also added: “The reds (‘Rossi’) on the board are a really interesting lineup. They range from lighter, food-friendly northern Italian reds to a full Amarone powerhouse.”

One thing immediately impressed me. ChatGPT wasn’t simply translating Italian into English. It explained unfamiliar grape varieties, described what I could expect in the glass, identified wines that were representative of the local region, and even suggested, based on what it knew about me, what two wines I would probably enjoy the most.

Now, one thing you should realize about ChatGPT and all AI is that they are not always 100% correct, and you may need to verify what they say. That was true in this case when it described the “Boemia sul Mare” 2022 (Franconia di Bolzano) – Prima Radice, and said, “’Franconia’ here likely refers to Schiava/Blaufränkisch-adjacent alpine styling from northern Italy.”

The server had said Franconia was a grape and is commonly known elsewhere as Blaufränkisch. I told ChatGPT, and it said that made more sense, and added, “And honestly, because you’re traveling and exploring wine culture, I’d probably order the Franconia first. That’s the kind of wine you almost never see outside the region.”

Now I have had Blaufränkisch before in the Finger Lakes, but I opted for that red wine. And the server paired it with baccala. This is cod, and as I had it in Portugal, it is called bacalhau there. It was another excellent wine and food pairing.

That was my first experience with using ChatGPT as my sommelier while I was in Italy. Rather than feeling overwhelmed, I suddenly felt confident enough to order wines I had never heard of before.

Florence

After seeing the statue of David in Florence, I sat at a roadside café to quench my thirst and looked at the wine list. Again, some of the wine names I recognized, but others were unknown. Armed with my knowledge of ChatGPT as my sommelier, I uploaded a photo of the white wine list and got back my personal recommendations.

“Since you enjoyed the Franconia and even tolerated the funky Durello, I suspect you’d probably enjoy:

• Ribolla Gialla
• Massovivo Vermentino
• Pomino Bianco
• Traminer (if you want aromatic).”

I love a good Vermentino since Texas wineries had already introduced me to Vermentino, so I was excited to taste one from its Italian heritage. I chose the Massovivo Vermentino, and it was very good. I told ChatGPT that I enjoyed it, to which it replied, “Good choice. Vermentino is one of those grapes that often overdelivers in Italy, especially along the Tuscan and Sardinian coasts… Honestly, Vermentino is one of the white grapes I wish more Texas wineries experimented with. In the right Texas sites, I think it could do really well because it handles heat and retains acidity nicely.”

ChatGPT knows that I own Texas Wine Lover and a lot of what my business entails. Hence, the nod to Texas wineries. I have been teaching it more about Texas wine since I started using it. This was another teaching lesson.

“We do have Texas wineries that produce Vermentino and do it very well. Duchman Family Winery makes a very good Vermentino. Portree Cellars recently started producing Fiano wines, and I wish I could have tried an Italian one. Perhaps in the next week and a half, I’ll find it somewhere.”

My Personal Sommelier

Over the next two weeks, our conversations evolved. At the beginning, I asked what a wine was. Soon I was asking which bottle best represented the local area, whether a grocery store purchase was worthwhile, how a wine compared with Texas examples, and what made a particular grape unique. ChatGPT had become less of a recommendation engine and more of a personal sommelier and wine educator.

One of the most enjoyable aspects of the experience was that AI never replaced the people I met. Restaurant servers still made recommendations, shop owners still pointed me toward local favorites, and I often compared their suggestions with ChatGPT’s. Sometimes I followed the server’s advice. Sometimes I followed ChatGPT’s. Frequently, they agreed, and when they didn’t, I learned something from both perspectives.

Rome

I had one day in Rome where our tour group visited attractions like the Spanish Steps, Trevi Fountain, and the Pantheon. We were set free around noon to do what we wanted to do for the rest of the day, and I had previously decided to walk back to the Colosseum area and then to the hotel. I found the wine bar Astemio Wine & Food along the route.

It was an impressive tasting menu of wines by the glass and even more by the bottle. I wish I had found the wine bar earlier while in Rome. It had more than three pages of wine by the glass. I uploaded the white wine page and told ChatGPT, “Okay buddy. I need a white wine that’s local to Rome or nearby.” Yeah, I was getting used to ChatGPT being my friend and sommelier.

I selected a Cotarella – Brut sparkling wine to freshen my palate, and it did the job.

Then I told ChatGPT I was trying to decide if I wanted to get a white wine or perhaps try a red. The response: “At this point, I’d probably lean toward a red just so you experience both sides of central Italian wine culture in one meal.”

It read my uploaded photo of the two-page red wine list and immediately said, “Now this is a much more interesting red list. 🍷”

It gave a few recommended wines and then said, “Cantina Sant’Andrea ‘Il Sogno.’ This is probably the most distinctly central Italian/Roman-area red on the menu because of Cesanese. Cesanese is the traditional red grape associated with Lazio and the Rome area. You almost never see it in Texas.”

That was a blend of Cesanese and Merlot, and after asking the tasting guide about it, they unfortunately didn’t have it. But they did have a wine that was 100% Cesanese, the 2025 Coletti Conti Anton Maria Hernicus Cesanese del Piglio DOCG. It was exceptionally good, and after confirming that with ChatGPT, it said, “This is actually a really nice find. It’s the kind of wine that many visitors to Rome never get a chance to try.”

And yes, I eventually found a Fiano.

Lessons Learned

Chronologically, the journey mirrored my growing confidence. It began with learning about regional wines in Venice and Florence, including Franconia, Durello, and Vermentino. In Cinque Terre, I deliberately sought wines that truly expressed the region instead of defaulting to familiar varieties. Around Rome and the surrounding areas, I explored Castelli Romani wines, Falanghina, Cesanese, and even evaluated house wines in a hotel and bottles on grocery store shelves.

Because I own Texas Wine Lover, I couldn’t help comparing many of the Italian wines with what we’re producing here in Texas. Vermentino and Fiano were just two wines that used the same grapes, along with Aglianico, and of course, Sangiovese. I learned about some Italian grapes and wines that I had not heard of before, and in the process, I believe ChatGPT also learned more about Texas wines when we compared.

The biggest lesson from the trip wasn’t about artificial intelligence. It was about curiosity. At Texas wineries, I often encourage visitors to move beyond Cabernet Sauvignon and Chardonnay. Texas grows an incredible diversity of grapes, and you never know which unfamiliar varietal may become your next favorite. Italy reminded me that the same philosophy applies wherever you travel. Every region has wines that tell the story of the place far better than internationally familiar grapes ever could.

Looking back through the conversations after I returned home, I realized that ChatGPT and I had discussed more than twenty different grape varieties during the trip. Some I knew well. Others I’d never heard of before. Instead of feeling intimidated by unfamiliar names, I found myself looking forward to discovering the next one.

So, would I use ChatGPT or another AI tool again as my personal sommelier? Absolutely. Not because it always picks the best wine, but because it gives me the confidence to ask better questions, understand the answers, and embrace local wines I might otherwise have overlooked. Whether you’re visiting Fredericksburg, Rome, Cinque Terre, or the canals of Venice, curiosity remains one of the best companions you can bring to the table. If AI helps spark that curiosity, then I’d say it’s earned a seat beside the wine glass, and I’ll toast to that.

As I boarded my flight home, I realized I hadn’t just discovered new wines. I discovered a new way to travel. Instead of feeling intimidated by unfamiliar wine lists, I now saw them as invitations to learn. That’s a lesson I’ll bring with me whether I’m visiting a winery in Texas, sitting at a café in Italy, or exploring another wine region somewhere else in the world.

Tips on using ChatGPT as your sommelier:

• Upload photos of bottles or menus
• If you use Live Photos on an iPhone, it’s okay to upload from your mobile device using the ChatGPT app, but if you’re on a computer using ChatGPT with the web browser, it doesn’t understand HEIC files. You’ll need the file to convert to something else, like JPG.
• Tell ChatGPT what you tasted and if you liked it. Let it learn what you like and don’t like.
• Ask questions. Don’t be shy and put as many questions as you want in one prompt instead of having prompt after prompt.
• Tell ChatGPT how much you want to spend or any other particular things you are looking for when deciding on a wine.
• Compare ChatGPT’s recommendation with your server’s recommendation. Sometimes they’ll agree. When they don’t, ask why. That’s often when you learn the most.
• Use ChatGPT BEFORE your trip to help you find wineries, wine bars, or other establishments.