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How to talk with strangers when traveling

Italian family in Venice — Italian Family, we met in Venice

Beginning example: We scheduled a trip to Italy beginning in Venice. We love Venice because we just get up, eat and get walking! Venice is a never-ending joy of a city for walking, shopping taking photos, and talking with strangers. The question becomes, should I enter into a conversation with the stranger or not. If I do, how do I do it naturally. Below are ideas to consider and examples of the interaction.

Our last trip to Venice was in ’19, and we came across a family that was also out shopping. As we approached them I said, “Wow, look at this great family! Are you from the Venice area?” I have found that there are many people in Italy that speak English very well, and the father answered, “No, We are from the Tuscany area and are here for a holiday. We enjoy being together in Venice.”

The kids were all smiles and I asked if I could take their picture. The kids were eager with smiles and the father and mother agreed, and the result is the photo above. We could have walked right by, noticing them but not talking and not having a moment with a local family out on a family holiday. Would we have missed something? Yes, the connection, the brief contact, the moment of human interaction, the above picture of a very happy moment. Your vacation is greatly enhanced with encounters as described.

Do you know what happens when you travel anywhere, to a state park, to the next state, to a different country? You see people, you ‘run’ into people, you are with others. What do you do most of the time? You just keep right on going with your agenda not initiating a discussion, a conversation. Why? In most cases, it is a ‘bit uncomfortable’. And you are right.

Ron and Jane at the Spanish Steps — Jane and I on the Spanish Steps in Rome

However, you are missing a huge part of your travel enjoyment. Yes, the scenery is beyond belief, the food is amazing and your travel companions are always fun and there to converse with. ….. And so are the people you see, the people you ‘run’ into; they are a part of your travel experience and the more you engage with them the greater will be your ‘travel reward’. Your travel story will now include: “We met this couple and they were from, ……, and they told us about……”. You did not just ‘see’ them or ‘run’ into them, you talked with them, and you got to know them in a brief but enriched way!

When you travel you have the opportunity to converse with those you do basic business with, the waitress, the shop owner behind the counter. These conversations are rote, they are limited and fit the context of the encounter.

But do you expand upon these brief conversations? “How?”, you may ask, and the answer to this question is the answer to the age-old question, “How do I become a good conversationalist”?

YOU ASK QUESTIONS! The art of asking great questions isn’t just restricted to consulting. In any industry, people with this skill are seen as more empathetic. They also lower the threshold for others to speak up, increase the quality of decisions, and foster collective intelligence. (Fadem) Questions that are on-topic or, more importantly, off-topic will stimulate conversation.

To the shop owner, as you finish your purchase: (as an example) “Do you live nearby?” Or “How long have you owned this shop?” Or, a bit more inquiring, “As you know, we are on a vacation. Where do you and your family go on your holiday?” These questions and they are unlimited, open up the opportunity to know just a bit more about a person that is living in an area that you have never been to before, about a culture that is ‘foreign’ to you, and by asking, you get an idea of what life is like in this part of the world.

A stranger just expanded your world, your travel is now much richer. It has become a person-to-person experience, not just a person-to-scenery experience. The enjoyment has greatly expanded, you conclude the events of the day with memories that actually include a stranger, a person and who that person is, and what that person is about. This person is now no longer a stranger. That is really the reason you travel, to get to know the people.

I might add a secondary ‘rule’ here for you to consider depending on the conversation and the situation. As you ask your question be sure to LISTEN to what is really being said, and where appropriate, ask a follow-up question to get more detail, to get just a bit deeper into the answer that was given.

How to listen and speak to strangers — Food Tour in Travesterre, Rome

The idea is to continue the‘ conversation’ with questions first and your comments second, as they fit. By asking questions you are showing interest and value to the other person, and when this encounter is completed, the other persons’ life is enriched also. This act of listening and following up with a related question is harder one-on-one that in a group.

Let me give you a couple of examples:

1. Venice Street Artist Jane and I were walking the ancient streets of Venice. As we were passing a small neighborhood cathedral, there, on the walkway leading to the cathedral, was the Mona Lisa, or rather, a drawing of the Mona Lisa.

Sidewalk artist in Venice — Matteo, a sidewalk artist in Venice

It was drawn with the utmost perfection. There were drawing tools around, a cloth, pastel chalk, and a chalk holder. Where was the artist? Several people were admiring, and I asked, to no one in particular, “Where is the artist?” Off to the side was a somewhat shy, small-in-stature Italian man. I went over to him and what did I do? I asked him a question, “You really drew this piece of art?” “Yes”, he said in broken English. “Have you been doing this all your life?” “Yes, I have always had an interest in art. I was trained at …..” and he stated some unknown Italian art school. “Why do you draw on the sidewalk?”

And he proceeded to tell me about the ‘sidewalk’ chalk art contests throughout the world. He had recently returned from the states where he took 1st in Philadelphia and 2nd in Orlando. We spoke for some time and I came away with an experience that lives with me to this day. Why? Because I asked an initial question and showed interest in HIM by listening and carrying on the conversation with other pertinent questions.

For the record, his name is Matteo Appignani, and this is his website.

2. Young girl on Mykonos After spending a very delightful day on the island of Mykonos, we passed a young girl on our way back to the ship. She was sitting and leaning against a wall asking for money by holding a plastic cup. I stopped and asked her a question, “Can I take your picture?” She smiled and said, “Yes.” I did not get her name but I asked, “Do you sit here each day?” She said, “Yes, my family needs the money and I know this is the best place to get money.”

I said, “You are right. You seem like a very nice young lady.” She said, “Thank you.” I proceeded to take her picture and give her some money and went on my way. Later on, when looking through the pictures of Mykonos, I saw her sitting there and truly remembered how she had touched my heart. A brief encounter but it enhanced my travel experience in a special way.

One last example.

3. The Artist Shop and the B&B There is an interesting connection in the following story uncovered through questioning and follow-up conversations. It became apparent as we traveled to the Tuscany area of Italy in 2015 and then again in 2019. Jane researches intensely and found an artist by the name of Adelina Quadri, a watercolor painter, in Monticchiello, a small town between Pienza and Montepulciano. So our 2015 trip included the purchase of a small watercolor landscape. Jane had a delightful visit with Adelina and was pleased with her purchase.

In 2019 her planning included a stay at a B&B by the name of Casa di Adelina In Monticciello (www.lacasadiadelina.eu). She was curious if there was a connection to the artist. As we arrived at the B&B we were greeted by a strapping, tall, dark, and very handsome gentleman. He said, “My name is Francesco. Where is your luggage?” We pointed, he grabbed, and both large pieces went up the stairway, three stories, and into our room in a flash. He directed us to our room and there we found not only our luggage but a room that was decorated in a rustic Mediterranean style with soft warm colors. Charming.

He came into our room to see if all was OK, and Jane asked, “Is Casa di Adelina named after your mother?” She was making the connection and was checking it out. He said, “Yes.” he said a bit confused. Jane enlightened him from the last trip. Jane followed up with the question, “Did you purchase it from your mother?” He laughed and said, “This is my family home.

Our family has owned the building for some 600 years. In Italy a property just passes from one member to another, we don’t sell our family homes.” I was shocked, the home was older than the United States of America!

Jane then went on to tell him of our prior trip and this was why she picked out his B&B.

Over the three nights stay we enjoyed our friendship with Francesco and especially the gourmet breakfasts that he cooks each morning. If you are in the area you MUST book this B&B!

Breakfast table setting — Breakfast ready to be served

Another last example:

On one of the mornings I got up early and sat reading in a room w ell decorated with couches, chairs, and a long eating table and chairs. I looked up and a young gentleman entered and he asked me a question! Imagine that, he beat me to it! “Where are you from?” I answered and he indicated that he had noticed that I was reading my Bible.

He proceeded to tell me that he and his wife were members of the Navigators, a missionary group, and were on their way back home to Mexico City. We had an immediate connection because I knew him and he knew me! Later that evening we were out to dinner at Daria’s and Roy and Monica walked in but there was no reservation. Jane noticed them leaving, got up, and asked them to join us. Needless to say, we had a very enjoyable dinner!