15 travel questions to start a conversation with other travellers
For shy travellers, striking up a conversation can sometimes feel like arriving at a brand new destination – maybe feeling a little bit lost and anxious but you’re keen to explore. Trust me, I’ve been there too. As a shy solo traveller, I know the struggle of wanting to connect but not knowing where to begin. Through listening to what questions fellow travellers ask, and understanding what questions feel organic to me, I’ve developed a set of go-to travel questions to initiate conversation.
From general icebreakers to questions that would relate to a certain scenario while travelling, you’ll find a variety of questions that’ll help you organically kick off a conversation. And keeping in mind that everyone is different and you might not gel with the wording I typically use, I’ve also added some alternative ways to ask questions.
You’ll also find that a lot of these questions are open-ended questions, which mean that it’ll encourage a longer answer. However, where I have included closed questions, which usually can be answered by “yes” or “no”, I’ve added any relevant follow-up travel questions to help you continue the conversation.
Basic travel questions
You don’t have to start a conversation with some out-of-the-box icebreaker. In fact, I prefer starting conversation with basic travel questions because they feel more organic and natural to ask a stranger. These type of questions  are my go-to because they resonate with everyone and people’s answers often lead to opportunities to ask further questions and topics to drive the conversation. By asking fellow travellers about travel, their upcoming destinations or where they’ve been, you can discover common ground.
“What brought you to *insert your location city here*?”
A person’s response to this questions will  likely provide you with insights into their travel preferences. For instance, maybe you’re in Rome and they’re fascinated with ancient history. Or perhaps you’re in Mykonos and they came for the beach clubs and nightlife. Knowing why people came here also allows for both of you to share recommendations in the location.. It also creates opportunities for shared experiences and common interests while making conversation feel natural and open-ended.
Alternative ways to ask this question:
- What drew you to “insert your location city here”?
- What are the main things you want to see and do while you’re here?
“Where are you travelling to next?”
This question allows you to learn more about a person’s travel plans, interests, and experiences, and it can lead to discussions about destinations you both love or plan on visiting. This question also helps you connect on a personal level and can lead to valuable recommendations and insights for future travels for both of you.
Alternative ways to ask this question:
- Whereabouts are you off to next?
- Where are you heading after *insert your current city/ town*?
“Where’s your favourite place you’ve been so far?”
This question can lead to lively discussions about travel highlights, hidden gems, and bucket-list destinations, creating a shared sense of excitement and adventure. It also provides an opportunity for you to exchange travel tips, recommendations, and maybe even make a few additions to your travel bucket list.
Alternative ways to ask this question:
- What’s your favourite country/ city?
- What’s one place in the world that you could travel to and never get tired of?
Solo travel questions
Sharing personal solo travel stories and perspectives is a way of bonding with fellow solo travellers – because it’s very likely that you’ve experienced similar challenges and feelings. Questions around solo travel allow you to shares stories and tips with one another.
“How long have you been travelling solo?”
This is a great conversation starter for fellow travellers if you’re both flying solo. It shows an interest in their personal journey, travel experiences and provides an opportunity to bond over shared experiences and challenges of solo travel. This question can lead to discussions about solo travel tips, memorable moments, and personal growth along the way.
Alternative ways to ask this question:
- When did you start travelling solo?
- When did you start going solo on your travels?
“What inspired you to embark on solo travel?”
This question can lead to meaningful discussions about self-discovery, independence, and the desire for adventure and exploration. This question may often lead to deeper conversation, as you will learn more about the person themselves. It also allows for sharing insights, tips, and reflections on the transformative power of solo travel.
Alternative ways to ask this question:
- How did you start travelling solo?
- What made you begin travelling solo?
Day tour setting questions
Engaging in conversation while you’re on a day tour can be tricky when it takes you a while to come out of your shell, as you know the connection and shared experience will be fleeting. You’re also more likely meet a variety of people so my go-to icebreakers would be a mixture of basic travel questions and a recommendations for the area you’re currently in.
“Where are you from?”
A classic and effective conversation starter when meeting travellers in any scenario. This question often leads to  discussions about home towns or cities and cultural differences. You may you even visited on another’s hometowns before – or you plan to, which might lead to reminiscing on past adventures or sharing recommendations.
Alternative ways to ask this question:
- Where’s home for you?
- Where do you call home?
“How long are you travelling for?”
This opens up the opportunity to learn more about their travel journey, destinations they plan to visit, and any exciting adventures they’ve had already. Additionally, if you discover any common experience in their answer, it might give you an opportunity for you to share your own travel experiences, recommendations and tips.
Alternative ways to ask this question:
- How long is your trip?
- How long do you plan to be away for?
“Have you been on any other day tours since you’ve been in *insert destination*?”
By asking this question, it allows you to exchange experiences and recommendations about local day tours – maybe ones you didn’t even think of doing! It shows interest in their experiences and provides an opportunity to learn about hidden gems or must-see attractions in the destination.
Alternative way to ask this question:
- Have you taken any other day tours in *insert destination*?
Follow-up question if they have been:
- Any that you’d recommend?
Follow-up question if they haven’t been:
- Do you often book days tours or do you usually make your own way around?
“Have you been to any cafes or restaurants that you would recommend here?”
For some people, food is a love language so sharing their culinary experiences and local favourites can be a great conversation starter. It provides an opportunity to exchange tips and recommendations for cafes, restaurants and bars in the area. If you’re both foodies, this question can also lead to discussions about different cuisines, food cultures, and unique dining experiences, and shared enjoyment of good food.
Alternative ways to ask this question:
- Do you know of any good *cafes/ restaurants/ bars* here?
- I wanted to find a good *insert local cuisine/ dish*, have you tried that anywhere here yet?
- Any cafes or restaurants you’ve tried and loved here that you’d recommend?
Hostel setting questions
In a hostel setting, not only do you have your love of travel in common with your fellow travellers but you’re also in the same location. Questions that work well in a hostel setting are often those that ask for recommendations or how the other person have been finding the destination so far. While the below questions will definitely help you to break the ice with fellow travellers in your hostel, they might even lead to finding yourself someone to explore with while you’ve both in the location.
“Have you been in *insert destination* long?”
Asking this question allows you to gauge how familiar the person is with the destination. It opens the door to discussions about their experiences and impressions so far. And if they’ve been there for a while, this question can also lead to an exchange of favourite spots, hidden gems, and memorable moments they’ve had during their time in the destination. If you’ve already spent some time in the location, it also provides an opportunity for you to share your own insights and recommendations.
Alternative way to ask this question:
- How long have you been in *insert destination* for?
“Do you have any recommendations of places to see?”
This question allows fellow travellers to share their favourite spots and hidden gems. It opens the door to discussions about must-see attractions, off-the-beaten-path destinations, and unique experiences in the area. This question also provides an opportunity for you to discover new places to explore and gain insider tips from someone who knows the destination well.
Alternative ways to ask this question:
- What places would you recommend so far?
- Have you been anywhere that you’d recommend?
“Do you have any cafe, restaurant and bar recommendations around here?”
Asking this invites travellers to share any good food or drink spots in the area. If you’re both foodies, this question can lead to discussions about delicious meals, cozy cafes, and hidden culinary gems. It might even open the opportunity for you to check somewhere out together!
Alternative ways to ask this question:
- Do you know of any good *cafes/ restaurants/ bars* here?
- I wanted to find a good *insert local cuisine/ dish*, have you tried that anywhere here yet?
- I’m a huge fan of *cocktails/ beer/ wine/ trying local spirits*, do you have any places you would recommend?
- Any cafes or restaurants you’ve tried and loved here that you’d recommend?
“Have you been to *insert place you want to go in current location*?”
This allows you to gauge their familiarity with a specific destination or attraction in your current location. This question can lead to discussions about their impressions, recommendations, and helpful tips. Additionally, mentioning your interest in visiting the same place may open up the possibility of going together.
Alternative ways to ask this question:
- I’m planning to go to *insert place*, have you been?
- Any chance you’ve been to *insert place* yet?
Follow-up question if they have been:
- Would you recommend it?
- How did you find it?
Group tour setting questions
The best thing about group tours is once they’ve begun, you’ll very quickly be making memories and bonding over shared experiences. But the first day or two, you’ll likely still be meeting all of your group members so questions about where their from and their travel experience is a great way to start a conversation with fellow group members.
“Where are you from?”
It’s a simple yet effective way to break the ice and get to know your fellow group tour travellers. This question opens the door to discussions about where you’re both from and cultural backgrounds. This allows you to find common ground for further interactions and build connections within the group.
Alternative ways to ask this question:
- Where’s home for you?
- Where do you call home?
“Have you been on a group tour with *insert tour company* before?”
This question is typically a closed question (can be answered with “yes” or “no”) but it can lead to discussions about past tours, tour company comparisons, destinations visited, and travel experiences. They might even recommend a tour you’ve not heard about that interests you.
Alternative ways to ask this question:
- Have you travelled with *insert tour company before*?
Follow-up question if they have been:
- What tours have you done with them in the past?
Follow-up question if they haven’t been:
- Have you been on a group tour in the past with a different company?
- How are you finding this opposed to how you’d usually travel?
“Is this your first time to *insert current destination*?”
While it’s another yes or no question, this is a natural way to strike up a conversation and learn more about each other’s travel experiences. This question opens the door to discussions about past visits to the destination or first impressions.
Alternative way to ask this question:
- Have you been to *insert current destination* before?”
Follow-up question if they have been:
- How long ago were you last here?
- Is it much different from the time you were here?
- Did you travel with a tour on that trip too?
Follow-up question if they haven’t been:
- How are you finding it so far?
Travel is all about embracing the journey, stepping out of your comfort zone, and opening yourself up to new experiences – which might just be breaking the ice and striking up a conversation. And who knows, you might just find yourself in a really memorable conversation or you might even find a lifelong travel buddy along the way!
For more tips on making friends, navigating hostels and group tours as a for shy traveller, check out more posts here.
