What happens when siblings lead a Backroads trip together? Meet Simone and Roberta Loperoti, who have spent a lifetime learning how to work together. Their sibling bond, shared sense of humor and complementary strengths create a dynamic guest experience that feels equal parts travel, storytelling and family tradition.
Great Backroads co-leaders often seem to share a brain.
They finish each other’s stories. They anticipate each other’s needs. They somehow know exactly when it’s time for a coffee stop, a history lesson or a joke.
Usually that’s the result of the many trips they’ve led together. But for Simone and Roberta Loperoti, it’s the result of sharing the same room through childhood until they were teenagers. They’re brother and sister.
“We’ve always been a great team,” says Simone. “Not the typical brother and sister fighting each other, but the two of us fighting the world.”
Following Big Brother
Somewhere along the way, Roberta decided she wanted to be wherever her brother was. She followed him to the same high school so they could commute together each day. She preferred his hand-me-down clothes to the outfits her mother picked out for her. And when Simone’s First Communion rolled around, she refused to wear the floral dress her mother had bought.
She wanted the same suit her brother was wearing.
So their mom got her one.
Two Leaders, One Story
The fact that they ended up in the same job almost seems inevitable in hindsight.
They’re both travelers. Both talkative. Both drawn to new experiences. Both willing to take risks. They share the same taste in music, many of the same friends and, apparently, the same tendency to fill a room with energy.
At one point, Simone finally asked the obvious question: “Why did we wait so long to work together?”
When Family Comes Along for the Ride
When they eventually got scheduled on the same trip, guests got more than two Trip Leaders. They got stories about grandma’s Sunday lunches. They got stories from Rome.
And by day four, they got a front-row seat to the Loperoti family dynamic. A casual coffee talk somehow turned into a spirited conversation about Italian family traditions and childhood memories.
According to Simone, this happened because Roberta “cannot be silent for more than 10 minutes in a row.”
Naturally, she joined the conversation.
“I loved talking about our little family,” says Roberta. “While we were talking, I realized how many great memories we have.”
Two Sides of the Same Story
The siblings also discovered that leading together felt suspiciously easy.
Asked to compare their leadership styles, neither could come up with many differences.
“Oh mamma mia,” says Roberta. “We literally have the same style. It was like looking at myself, just with better communication skills and better curly hair.”
Simone has his own version: “It was like being in front of the mirror but looking better than usual.”
There are some distinctions. Roberta is more focused on details and history. Simone gravitates toward jokes and making sure everyone is having a good time. Mostly, though, guests saw two siblings being themselves.
That meant hearing different opinions on the same topic. It meant watching them tease each other. It meant seeing two people who clearly know each other well enough to disagree without making it a disagreement. As Simone put it, guests got “two sides of the same story.”
Bellissimo, Together Again
One guest summed it up better than we could: “I hope one day my kids will love each other the way the two of them do.”
As for whether they’ll lead together again?
Both seem pretty clear on that.
“BELLISSIMO!” says Roberta. “I would love to work together again.”
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