An Unlikely Friendship, Born in Tuscany
It started like any other cruise excursion—crowded, sunny, and slightly chaotic. But somewhere between the vineyards, the heat, and a snide remark, I found myself laughing with a woman I’d just met. I didn’t know then that Ms. Leon would go from stranger to friend to jazz-show companion back home in San Diego. Funny how a shared bottle of wine and a natural language of snark can turn a day in Tuscany into the start of something lasting.
Finding Familiar Faces While Traveling Abroad
One of the great things about traveling the world is that you’re never really alone. There are always other people out there exploring, too. Maybe not in the same way you do, but they’re out there. And while I love meeting locals when we travel, we often find ourselves connecting with fellow Americans as well.
That’s especially true on cruises. No matter where a cruise begins or ends, U.S. citizens tend to favor primarily English-speaking cruise lines. So it only makes sense that you run into a lot of familiar accents—and not always a wide variety of cultures.
Over the years, we’ve met people from all over the world and made friends in the Netherlands, Canada, England, Australia, and across the United States. But there’s one particular friend we made on a cruise whom I now get to see all the time.
Our Mediterranean Cruise: The Start of Something Unexpected
When we took our whirlwind 40-day retirement trip in 2024, we kicked it off with a 14-day Mediterranean cruise departing from Civitavecchia, Italy. We fell in love with that port city (you can read about it here).
Our very first stop was Livorno, where we joined a full-day “Tuscany Countryside & Wine Tasting” excursion. It took us to Montecarlo de Lucca to wander a charming Tuscan village, then wound through the countryside to a small wine cellar where we toured the vineyard and sat down for a wine tasting lunch. A very typical Tuscan day.
Looking out over the Tuscan Valley from Montecarlo de Lucca, Italy. / Photo by Whaldo Digital Content
A Classic Tuscany Excursion—With a Twist
We boarded a coach with about 60 other passengers. After strolling the village and snapping a few photos, we were herded to the vineyard and invited to join a short tour. Some people opted out—it was hot, and they just wanted to sit. But my husband and I went, as we always do. Why travel if you’re not going to explore?
At the corner of the vineyard, the guide explained what they were growing and producing. It was a scorcher of a day, and little by little, our small group drifted under the olive trees for shade. Some people were engaged, asking questions, and eager to learn. We were all here to see something new—and sip something good.
The Vineyard, the Heat, and a Perfectly-Timed Remark
After the guide finished her talk, we made our way toward the canopied tables set for lunch. As we walked, the guide began pointing out some old machinery. That’s when I first heard her voice.
I don’t think she meant for us to hear it, but there it was: “Ah yes, the rusted machinery tour—every girl’s dream when she books Tuscany.”
My husband giggled and softly agreed, “Right?”
That’s when the three of us—me, my husband, and the voice—looked at each other and grinned. We all laughed and kept walking.
We came upon a horse baking in the sun. I offered, “Ugh, I wouldn’t want to be him right now.”
She didn’t miss a beat: “We’ll all smell like him after this excursion.”
To which I added, “Great. Eau de Barnyard—the scent of summer.”
I immediately liked her. Snark is my native language.
Laughter, Lunch, and a Table Full of Strangers
The three of us walked to the canopied luncheon area and let the staff seat us. I was happy to see she was placed across from me. We all gulped cold water and settled in.
The staff described the dishes we’d be sharing and the wines being poured. Introductions began, as they often do at communal tables.
To my husband’s left: a foursome from Southern California. To my right: another foursome from Southern California. Across from us: our new friend Ms. Leon, from San Diego, and “William” (not his real name, because I can’t remember), from Australia.
Naturally, everyone was fascinated by how long it took William to travel to reach Rome. But soon enough, the two SoCal groups returned to their own conversations, leaving my husband and me chatting with Ms. Leon and William.
It wasn’t lost on us that we were 6,500 miles from San Diego, and somehow still surrounded by Californians—and one Aussie.
Lunch was delicious—olives, tapas, olive oil, several wines, and a surprising little chocolate candy filled with citrus liqueur that burst in your mouth with bright, addictive flavor. Conversation flowed. Laughter came easily. We all bought a bag of candy.
After the tour, we returned to the ship.
Martinis, Music, and Missed Connections
That evening, freshly showered and dressed for dinner, my husband and I stopped by the bar for a happy hour cocktail. In walked Ms. Leon, ordering a martini. As soon as we made eye contact, the three of us struck up another easy conversation. She went off to dine with her two travel companions, and we headed to listen to a band before dinner.
We saw Ms. Leon at happy hour for a few more nights—until she didn’t show. We assumed she was off with her friends, but when she reappeared a couple of days later, we learned she’d been ill. (We’ve experienced that a few times; you can read my post about it here.) After that, the occasional happy hour resumed.
The Mystery of the Misplaced Bag
A few days later, in Marseille, we were waiting to board our coach for another excursion when I saw Ms. Leon weaving through the rows of seats, clearly upset and looking for something. I got up and asked if I could help.
She had accidentally left her bag behind. The problem? It was the standard cruise line-issued bag that everyone was carrying. She’d returned to where she was sitting earlier and asked the man now in that seat if the bag next to him was his. He said yes.
Still no bag.
I suggested she ask the staff to make an announcement. She went to the front, and they did. And wouldn’t you know it—the same man picked up the bag and called out, asking if it belonged to anyone.
It was hers.
Ms. Leon summoned every ounce of composure to walk back to him, take her bag, and offer a polite “thank you.” But the second she reached me, the sass returned—dry, biting, and laced with disbelief.
“Right. I point right at it and ask him if it’s his—‘Yes.’ Then the woman with the microphone says the same thing, and suddenly he’s Sherlock Holmes.”
She rolled her eyes so hard I thought she might actually strain something.
“Next time, I'm just showing up with a full gospel choir and a giant arrow made of lasers pointing at my bag. Apparently, that's the only way to get through to some people.”
She went on her way with her friend. I sat down beside my husband, still laughing.
Snark, when delivered well, is usually rooted in truth—bitingly funny, and unmistakably snide. Ms. Leon is fluent in snark.
We kept finding each other at happy hour, and over the course of the cruise, we developed a friendship. Before the trip ended, we exchanged contact info and promised to meet up when we returned to San Diego.
Back in San Diego: From Cruise Friends to Real-Life Friends
That cruise was only the beginning of our 40-day adventure, so it would be nearly a month before we were home. But once we returned, I reached out—and the friendship picked up right where it left off.
Our first outing happened by accident. My husband and I were at a Trombone Shorty concert at the Rady Shell in San Diego. Before the show started, I texted Ms. Leon to let her know we were there, knowing she loved jazz and had seen the same show. She replied immediately—she was there too! I told her where we were (up on the grass), and she came over for a pre-show drink.
Since then, we’ve had lunch dates, dinner dates, and even caught another fantastic jazz show at Jacob’s Music Center.
Unlikely Friendships Are the Best Kind
We’re very different women, Ms. Leon and I—an unlikely pair, to be sure. But we share the essentials: good music, good wine, good food—and fluent snark. When we’re together, there’s always laughter.
It just goes to show—you can be anywhere in this great big world and meet your soul sister. Never underestimate the power of being friendly and open to new connections.
Stay curious. Stay kind. And always stay a little bit snarky.
– J.S. Whaldo
