Skip to main content

I’m finishing up my small portion of the guidebook updates for Rick Steves, and was thinking a bit about all of the characters I have encountered along the way. Travel is fun because you get to see beautiful things and eat unusual food, generally enjoying new experiences. One of the surprises for many travelers, I have observed, is how much they enjoy the people they meet, both other travelers and locals.

I am actually painfully shy in reality, even if most people don’t think that could be true. My mother used to bribe me to talk to strangers-no kidding! She’d give me money to buy cookies at McDonald’s and make me order them, just so I would interact with other people. I’ve worked hard to overcome that, but it’s still there on some level.

So, being in a realm where I have to talk to strangers on a daily basis, and in a foreign language, has been an interesting challenge. I share this personal detail mostly because I want to encourage other shy people to try to break out of that shell while traveling. Being friendly and open, striking up conversation with locals whenever the opportunity presents itself, this is a skill that pays off in incredible ways. Believe me, I’ve got crazy stories about people I’ve met. Lots of them. Here are a few from this past week.


Hotel owners are the easiest characters to meet. Most people go into the hotel business because they are outgoing and enjoy meeting people. The hotels listed in our books are usually places we have known for years and the owners are often very friendly, like extended family. I don’t usually have enough time to get to know them well, but occasionally someone throws me a curveball and is so interesting that I have to take some time to get to know them.

One of my closest girlfriends was a hotel owner in the Rick Steves guidebooks. I walked through her door, we looked at each other, and many bottles of prosecco later…we were besties. It happens like that sometimes. I consider it divine intervention.  

On my most recent trip, I met a lovely woman in Orvieto named Francesca. I had a tough time tracking her down, she is a mom and was all over town with her kids, I can relate to that. By the time I finally caught her, it was worth the hassle. She was so funny and delightful, and her B&B was inviting. What was most intriguing for me was her last name, Michaelangeli. If you’ve ever been to Orvieto, you may have seen wood sculptures all over town. These sculptures were done by a famous workshop, the Michaelangeli workshop.

I asked her if there was any relation and she looked up at her kitchen cabinets. They were cute, handmade cabinets, a little unusual in style. She said, “These cabinets, they were made by the same man, they were for the tools and I took them when they were discarded. The artist you see all over town was my grandfather.”   I was so surprised and kind of star struck, I’ve always admired the fun sculptures all over town but never knew the story.

Her grandfather worked with his brother for many years, they became world famous, showing their work in galleries and doing installations as far away as Japan. She told me her aunts are now in charge of the bottega (the workshop) and that they continue the line, selling their work worldwide. She invited me to come back and tour the workshop, which I hope to do this summer. Besides her family’s fame, she was such a bubbly person, I learned a bit more about her town and enjoyed coffee and a slice of homemade cake with a gorgeous view from her terrace. 


You can find a decent meal just about anywhere in Italy, but it seems to me that you get exceptional meals at restaurants run by characters. I was reviewing our restaurant listings in Cortona and went in to check out a higher-end restaurant called La Bucaccia, which roughly translates into “the big hole.” It was the end of lunch and the owner, Romano, greeted me with a flourish and a kiss on the hand. He invited me to come back in the evening for dinner so that I could get a better feel for what he does, as things were dying down after the lunch service.  I’m not really one to pass up an invitation for a nice glass of wine, so I agreed.

I came back about 8:00 and the restaurant, outside of a couple with a baby, was dead. He greeted me again like a showman and sat me down, taking the chair next to me to go over the menu. I thought that was a nice touch but probably done because of why I was there. But not so. The Italians started arriving in a steady stream at 9, and he sat with each table and chatted them up, guiding their choices and vetoing bad decisions with a puff of air and an eye roll. Then the show began.

He worked the room, making jokes to each diner but addressing the whole room, presiding over the meal. He got out a big knife and a bigger leg of prosciutto, carving off slices and teasing the diners as he lopped off the meat. The jokes were flying fast and furious, although I won’t translate them for you…this is a family blog you know. After many laughs, the men were all hugged on the way out the door, the ladies kissed. It was such a fun and personal experience, and, oh yeah, the food was really good too.

Other Places 

I’ve gotten so bold about chatting with the locals that I have fun talking to people in shops, wineries, piazzas, just about anywhere. Italians love to chat and being a 6’2″ blonde woman, I sort of stand out. Just speaking Italian is enough to get some curiosity going, and people often remember me.

I returned to visit one of the most colorful characters in Tuscany, the host of a wine cellar in Montepulciano, Adamo of Cantina Contucci. I first met Adamo about 10 years ago, as I was working on the first edition of the Florence and Tuscany book. I was looking for a winery to add and dropped in to Contucci, which is right in the heart of the village. Adamo greeted me then as he did years later, with a big voice and a bigger personality and passion for the wine. I recall getting a detailed tour through the cellar and an animated conversation.

When I visited recently, he was in the tasting room, holding court and gesticulating wildly. He looked over at me and invited me to join in. I told him who I was a he got a sparkle in his eyes. “You, you were here many years ago! And you were pregnant!” Which was true, I couldn’t believe it. After years, probably thousands upon thousands of customers, he recalled that detail. Adamo has been in working for Contucci since he was 15, he joked that he was doing wine tasting before he could drink it. He’s been there almost 60 years, in the same cellar every day. But his passion for the wines is so fresh and present, you’d think he was Bacchus himself and had just invented the concept of wine.

He was so thrilled to have a familiar face, he proudly pulled out an antique tool, one he saves for special occasions. It was a thin metal strip and he proceeded to show us how wine was decanted in the past, using a candle to illuminate the sediments. His pride in showing this ancient trick was a joy to witness. Italians use the word personaggio to speak about someone that is a colorful character. It sort of implies a scale, a grandness to the person, something big and unique that you will remember.

I have a hall of personaggi in my brain, like a long dining room in a castle with giant portraits on the wall, sort of like Hogwart’s. So many of the people I’ve met in Italy have found a place there, this is just a tiny sample as I’ve had many adventures with big personalities like these. I’m glad I’ve overcome my timidity, otherwise I’d have met no one, and the walls of the castle in my imagination would be bare.  

We’re here to help you plan your next adventure!

Already know where you would like to travel, but you are feeling a bit overwhelmed by the planning process? We can create custom itineraries to any destination in the world for groups of almost any size, or answer questions and provide recommendations. It’s best to contact us well in advance, so we have time to research and prepare, as well as find time in between leading tours in order to meet (virtually)!

AWS Staff

This post was published by the Adventures with Sarah team. Click here to find out more about the people that make everything at AWS happen.


  • Annette says:

    Loved this post, Sarah. It caused me to fondly remember some of the wonderful personaggi I encountered in my times in Italy. Thank you.

  • Heather Cohen says:

    Thanks Sarah, for another great read!

  • P T says:

    Sarah, what a wonderful post. I, too, am a teensy bit shy, but I flourish when traveling in South and Central America and get to speak Spanish. It is so fun! You are tempting me to learn Italian. But you have to answer a question: What is your final verdict on the puffy jacket?

    • says:

      I think that speaking in a foreign language actually helps the shyness somehow. I LOVE my jacket. I highly recommend it. I got a great deal through Amazon, it was about half of REI, I think there should be a link in the article. Best travel coat, warm and lightweight but also packs down beautifully. I only wish I’d have brought a stuff sack to store it in.

      • P T says:

        Thanks for the evaluation from one who followed your search. It looks great on you too, or rather, you look great in It! I haven’t the need for one yet, my hubby dislikes traveling in cold weather, as I love traveling with a leather jacket. I know, heavy, but it’s my guilty pleasure.

Leave a Reply