Ever feel a little awkward striking up a conversation with strangers while traveling? Like, when you’re sitting at a local bar or waiting for a tour to start, racking your brain for something to say (me too!). But don’t worry—that’s why I put together this list of super easy icebreaker questions to help you connect on the road.
A set of good questions to break the ice are important because they can help to get the conversation started and make people feel more comfortable (including yourself!). One of the best things about them is that they can be used in a variety of travel situations—from waiting at the airport to waiting in line for a show. Scan through my top picks, and select a handful to use at your next opportunity.
Questions To Ask Locals
When you’re in a new place, the first part about connecting with someone is figuring out who’s a local—and the easiest way to do that is by casually asking, “Are you from this area?” It’s simple, friendly, and sets the tone for a laid-back conversation.
If they say yes, jackpot! You’ve just unlocked insider tips that no guidebook can touch—like the best hole-in-the-wall cafes, hidden trails, or local spots tourists totally miss. Plus, locals love sharing what makes their home special. You can follow up with any of the following questions:
- What’s your favorite hidden gem in this area that most tourists miss?
- Is there a local dish I absolutely have to try while I’m here?
- What’s the best time of year to visit your town or city?
- Are there any local festivals or traditions happening soon?
- Where do you like to hang out on weekends?
- What’s the story behind this town or city’s name?
- Do you have a favorite place to watch the sunset around here?
- How do locals usually greet each other—handshake, hug, or something else?
- What’s a local saying or phrase that I should know?
- If I only have one day here, what should I not miss?
- What’s the best way to get around—walk, bike, or public transportation?
- Where’s the best place to grab coffee (or a drink) around here?
- Is there a local market or shop you love that I should check out?
- What’s something tourists often misunderstand about your culture?
- Do you have a favorite memory or story tied to this area?
- What’s the most beautiful place near here for a day trip?
- How do you usually celebrate holidays or special occasions?
- Do locals prefer early mornings or late nights around here?
- What’s your favorite thing about living in this part of the world?
- If I wanted to blend in and not look like a tourist, what should I do?
- Are there any local superstitions or beliefs I should know about?
- What’s a food here that locals love but visitors usually skip?
- Do people here prefer the beach, the mountains, or the city?
- What’s one thing you wish more visitors knew or appreciated about your culture?
- If someone wanted to move here, what advice would you give them?
Questions To Ask Travelers
One of the easiest ways to spark a fun conversation with fellow travelers is by asking, “What brought you here?” It’s casual, friendly, and gives them a chance to share their story—whether it’s a bucket list adventure, a spontaneous getaway, or just the search for the best local pizza. From there, the conversation can flow naturally—maybe you’ll swap travel tips, compare notes on favorite spots, or even team up for a tour or meal. If not, these questions will help:
- Where are you traveling from?
- Where’s your favorite place you’ve ever traveled to, and why?
- What destination is at the top of your travel bucket list?
- Have you had any funny or surprising travel mishaps?
- What’s the most delicious dish you’ve tried on your travels?
- Do you prefer mountains, beaches, or cities when you travel?
- What’s the most interesting person you’ve met on a trip?
- What’s your go-to travel essential that you never leave home without?
- Have you learned any new phrases in another language during your travels?
- Do you prefer solo travel or traveling with friends or family?
- What’s the longest trip you’ve ever taken?
- Have you ever gotten lost somewhere? How did you find your way back?
- What’s the most beautiful natural sight you’ve seen on a trip?
- Do you have any tips for avoiding tourist traps?
- What’s the coolest local tradition or custom you’ve experienced?
- Have you ever tried a crazy or exotic food while traveling?
- What’s a place that totally exceeded your expectations?
- What’s the best souvenir you’ve brought home?
- Do you have a favorite travel app or website you swear by?
- What inspired you to visit this destination?
- Do you collect anything from the places you travel to?
- What’s the most adventurous thing you’ve ever done on a trip?
- Which country or city surprised you the most, and why?
- Have you ever participated in a festival or celebration abroad?
- What’s the best street food you’ve tried while traveling?
- Do you prefer short weekend trips or long, immersive journeys?
- Have you ever stayed in a unique accommodation like a treehouse or a yurt?
- What’s the weirdest or most interesting transportation method you’ve taken?
- Do you like to visit museums, parks, or markets when exploring a new place?
- What’s the most memorable wildlife encounter you’ve had while traveling?
- Do you prefer guided tours or exploring on your own?
- What’s your funniest travel story?
- What’s one local dish you could eat every day?
- Do you have a dream destination for a future holiday?
- What’s the most remote place you’ve visited?
- Have you ever visited a place that felt just like home?
- What’s the most underrated place you’ve ever traveled to?
- What’s the best piece of travel advice you’ve received from someone else?
- If you could drop everything right now and travel anywhere, where would it be?
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