Hear from Jane & Phil:
How to Make Genuine Connections on Tour

That moment — when two strangers get so absorbed in each other’s company that they lose track of the world around them — is what makes group travel so exciting. “It was funny,” Jane said. “We had to go all the way to Sicily to meet somebody who lives 20 minutes from our house.”

Jane joined the tour alongside friends she’d made on our Enchanting Portugal tour, a group who’d got along so well they couldn’t resist booking Sicily & Southern Italy together. Phil was a solo traveller on a mission to connect with the country his parents had called home.

Bring 27 strangers to Sicily together, and something is bound to shift. When you’re all visiting a new place together for the first time, the destination itself does the heavy lifting. Having a shared context is what made Phil and Jane’s first conversations so easy. They started walking. They started talking. And they kept talking through dinners, through winery visits, and free afternoons wandering Sicilian towns.

The friendship that started in front of that restaurant carried through the rest of the tour. And back home, it became something more! Here’s what their friendship, and eventual love story, can teach us about making genuine connections on group tours.

1. USE THE WORLD’S BEST ICEBREAKER: SHARED EXPERIENCE

ICEBREAKER TIP: Ask your fellow group members what made them choose this specific tour, what they’re looking forward to the most, and about their past travel experiences to get the conversation flowing.

Group travel hands you a shared context. Throughout the tour, you watch the same sunset, taste the same wine for the first time, and step into the film The Godfather in the hillside village of Forza d’Agrò.  The conversation doesn’t need to start from zero!

Phil described how the group travel experience naturally helps break the ice. “Everyone has a common denominator of being in Sicily. Everyone likes good food and wine, so you’ve got that in common!”

Lean into the shared experience. Don’t wait for the “right” moment to talk to someone — the destination is already doing the work, and you just have to show up.

At the end of each day, Jane’s friend group began a tradition. They got together in the hotel lobby, shared Sicilian wine, and talked about the adventures the day brought. “We talked about what we saw that day and what we liked, and where we’re going the next day. You’re in so many different places and you want to take it all in — it goes by quickly. It’s nice to sit down afterward and talk about it,” Jane said.

Slowly but surely, Phil started joining these get-togethers and became part of the group. Making the effort to show up and get to know others led to friendships he hadn’t expected but was glad he found.

2. LEAN INTO THE FREEDOM OF A PLANNED TOUR

ICEBREAKER TIP: Without the stress of planning the tour, you can give your full attention to the person next to you.

Make the most of it! Kick back and sit next to a person you haven’t chatted to before. Those unhurried hours are when you can get to know someone. Nothing compares to the mental freedom an all-inclusive group tour gives you. You wander the city by instinct and end up somewhere you’ll talk about for years. With your mind off of logistics, the sky’s the limit!

Our tours are designed to create unforgettable travel moments for each of our travellers. Instead of just stopping at a few key sites, you get a well-rounded experience that brings you to various regions of your chosen destination, all worry-free. When the logistics are handled: the coaches, the accommodation, the guides, the restaurant bookings — you stop spending mental energy on planning and start spending it on being present.

“It’s nice, that you don’t have to think about anything,” Jane said. “You’ve got a [Group Guru] telling you what time you’re leaving in the morning — that’s all you have to worry about. Everything is taken care of and so well organized. Our [Group Guru] for Portugal was wonderful and for Sicily she was amazing — she couldn’t have done more for us. It’s a great way to travel because once you’ve paid for the trip, that’s it. The only extra funds you need are for souvenirs or wine. You just show up and stay open to new experiences — climbing lava mountains and all that. It’s comfortable and social.”

In Sicily, there was always something to look forward to for Jane and Phil. Mount Etna, the boat trip around Stromboli, the winery, and the local markets immersed them in Sicilian life. At the same time, the free moments between these excursions mean there’s room to breathe, and let a conversation run long without checking your watch.

3. KEEP IN TOUCH, KEEP THE GOOD VIBES GOING

ICEBREAKER TIP: After you’ve returned home, stay active in the group chat.

Plan the group dinner in Toronto you talked about. Be the one who looks into the next trip and mentions it to a friend. A little effort goes a long way when the foundation is already solid!

Here’s what you might not expect from group travel: it doesn’t end when your group says goodbye. Each tour group has a WhatsApp thread that keeps you all connected to your Group Guru, and this is a fantastic way to keep in touch with fellow travellers.  Sometimes a group chat stays active and you realize you’ve made a new friend to visit in Saskatchewan!

For Phil, keeping in touch meant doing something a little braver than sending a message in the group chat — it meant calling Jane and asking her out to dinner, and the rest is history.

Over time, you find your place. Your first tour gives you an experience and a set of people. Those people may become your future travel companions. Your second tour introduces you to many more. By the time you’re on your third or fourth trip, you’re part of community of people who share your curiosity and your willingness to discover new destinations.

TIPS FROM PHIL & JANE

Phil and Jane are now in Mexico, making the most of the sunshine and attending live music shows. They’re currently looking forward to a Signature Italy Tour in October — the same dates they met the year before!

Jane’s advice to anyone wanting to book an Approach tour is to: “Bring comfortable shoes. Be open to new experiences and meeting people. I think the more you put into it, the more you get out of it. If you’re willing to talk to people, you get so much more out of it. By the end of two weeks, you know each other’s families and hometowns. You know who the characters are. It’s really fun.”

Phil agrees: “Just enjoy yourself. With Approach, you don’t have to worry about anything.”

He was checking off a bucket list item — seeing the island his Sicilian parents were born on but never got to explore. She was returning to a tour company she trusted, with friends she’d made on a previous trip, to tick off another destination they all wanted to see.

Phil and Jane didn’t go to Sicily looking for each other. They just had to be present and willing to let a conversation run a little long, even if it means walking right past the restaurant.

They went all the way to Sicily to meet someone from just around the corner.

Sometimes that’s the exact distance you need.