Top Travel Questions | 200 Fun + Engaging Questions About Travelling To Ask

Fun Questions to ask Travel the world

Travelling the world is a dream for many, myself included. I quit my job in 2012 to travel and have been living out of a suitcase ever since. A countless number of adventures and an immeasurable number of conversations later, I think back on all the questions I’ve been asked through it all by fellow travellers I have met along the way as well as friends back home. Find a collection of these travel questions in this post. Answer as many as of these questions about traveling as you can and use them as conversation starters the next time you find yourself on an adventure of your own. 

If you’d like to know my personal answer to any of these questions,
feel free to contact me or start a conversation of our own on insta. Enjoy!

Whether you find yourself waiting at the airport, on an overnight journey by bus or train, or simply hanging with new found friends while abroad, these questions make for some perfect conversation starters and are sure to get the good vibes flowing

I’ve split this into sections to make it easier to read. You will find a list of fun travel questions, interesting and enticing questions about travelling as well as some random would you rather questions. Maybe you’re looking for some travel trivia or an engaging travel question for Instagram

— find it all ⬇⬇

Be sure to save this post or bookmark it to easily find it during your next journey. Let’s get into it….


What to ask people who travel?

Find a list of fun questions about traveling that are bound to keep the conversation flowing from beginning to end!

Travel Questions about travelling
  1. You win the lottery tomorrow. Where are you travelling to first?

  2. What is your favourite aspect about traveling?

  3. What is the weirdest food you’ve ever tried while traveling?

  4. What are sure signs of being a travel addict?

  5. Are you a city traveller or nature explorer?

  6. Have you ever hitchhiked? If not, would you ever consider doing it?

  7. Are you a member of the mile high club?

  8. Have you ever been on a cruise?

  9. Choose one famous person or celebrity to travel with?

  10. Have you ever flown first class?

  11. How many countries have you been to?

  12. What is your favourite city?

  13. Where you would you rather be right this moment?

  14. Do you prefer a window seat or aisle seat on a plane?

  15. What is the most exotic food you’ve tasted?

  16. Where is the weirdest place you’ve slept during your travels?

  17. Would you rather go on a safari, have a city break, or visit a tropical island?

  18. Have you ever been camping while abroad?

  19. What is your favorite travel song?

  20. How many of the 7 wonders of the world have you seen?

  21. What is the best and worst thing about travelling to a new country?

  22. Beach or mountains?

  23. What is your most valuable travel possession?

  24. Have you fallen in love while travelling?

  25. What is your favourite vacation song about summer and the beach?

  26. What movie and/or has inspired a previous trip of yours?

  27. What’s a funny or strange travel story of yours?

  28. Have you ever been on a safari?

  29. What is your drink of choice on a plane?

  30. What is you go to remedy for jet-lag?

  31. What is the favorite stamp in your passport?

  32. Do you have any embarrassing travel stories?

  33. What is the most adventurous thing you’ve done during your travels?

  34. What characteristics make for a cool travel partner?

  35. Have you ever been snorkelling? If so, where?

  36. What is the best gift to give to a traveller?

  37. Describe a dream travel experience?

Check out this list of the:
10 best cheap tropical islands to visit around the world


I am a huge fan of not just fun travel questions to ask, but also deep and open ended questions that are often accompanied with some insightful responses and interesting debates.

What are some questions about travel?

fun travel questions for instagram on travel to ask
  1. How does travel and seeing the world inspire you?

  2. How many countries do you want to discover in your life?

  3. How often do you travel? How many days in a month/weeks in a year are you away from home?

  4. Where do you feel most at home?

  5. What has been your biggest adventure so far?

  6. Why do you travel?

  7. What is the most exotic destination you’ve been to?

  8. What are some of the lessons that travel has taught you?

  9. What has been your worst trip or worst travel experience?

  10. What can you not travel without?

  11. Where is the most beautiful place you’ve ever seen?

  12. Have you ever made any of these mistakes while flying?

  13. How do you feel on your return home?

  14. What travel experiences are at the top of of your bucket list?

  15. When you’re not on the open road, what is the thing you miss most about travelling?

  16. Are there more advantages to travelling alone or with others?

  17. What is your best travel tip?

  18. What has been your biggest travel mistake?

  19. What cities would you love to discover?

  20. What is the best airport for a long layover?

  21. When you’re away, what do you miss most about home?

  22. Who do you usually travel with?

  23. What is the difference between a tourist and a traveller?

  24. Do you think its safe to travel during the covid-19 pandemic?

  25. Did you have any bad travel experiences?

  26. What has been the most stressful part about travel for you?

  27. If you could choose one place to live anywhere in the world, where would you most like to live?

  28. What is your main concern when travelling?

  29. Do you have a favourite airline?

  30. What is the scariest thing that has happened to you while traveling?

  31. When do you feel the most alive?

  32. Do you travel with a fixed plan or usually just wing it?

  33. What’s been the biggest struggle you’ve experienced about travel?

  34. What is your favorite childhood travel memory?

  35. How has corona covid-19 affected your traveling lifestyle?

  36. Do you think countries closing their borders was a good move?

  37. How do you feel about a travel pass?

The important of travel and exploring the world cannot be stressed enough.
Here are the 10 key advantages of travelling

Keep reading for more ideas + fun traveling questions to ask …


How do you talk about travelling?

In developing a conversation, few things compare to getting into the head of the other person. Here are a number of thought-provoking questions on travel to get to know someone a little better.

Engaging Questions about travel fun
  1. What do you think is the main benefit of travel?

  2. What does the concept of home mean to you?

  3. Is it the journey or the destination that’s most important to you?

  4. What motivates you to travel?

  5. What is the biggest barrier to long term travel?

  6. What about traveling do you enjoy the least?

  7. What is the very first place you’ve visited?

  8. What has been your best trip?

  9. Have you ever gotten really lost while abroad?

  10. What are some things you always take with you on a trip?

  11. What characteristics and traits are essential for being a traveler?

  12. What is your preferred means of transport when traveling?

  13. Do you have any destinations that you would not like to visit?

  14. What is the most beautiful city you’ve visited?

  15. Do you learn a few phrases of the local language before visiting a new country?

  16. Which country has the best food?

  17. What is your earliest travel memory of being on vacation?

  18. Do you make friends easily while on the road?

  19. What are some of the disadvantages of long term travel?

  20. Are you a fan of trying out local foods?

  21. How do you choose where to travel to? 

  22. Which places hold a special place in your heart?

  23. What’s the best travel advice you’ve received?

  24. What is your travel style? Relaxing beach island vacation or city-to-city explorations?

  25. What are your thoughts on ecotourism and being a responsible tourist?

  26. What is the worst injury you’ve gotten while traveling?

  27. Which island would you love to visit with your family?

  28. What would surprise people the most about long term travel?

  29. Are you enticed by the life of a digital nomad?

Care about how many countries you’ve been to?
Here’s why you should stop counting


It’s bound to be an interesting and enlightening talk with these deep thinking questions for a travelling companion.

How do you ask travel questions?

Fun Travel questions to ask
  1. How has travel changed you throughout the years?

  2. What is your favourite part about travel?

  3. Where did you travel to internationally for the first time?

  4. If you could travel to anytime in the past, where would you go?

  5. Where would you love to explore next?

  6. Where was the last place you’ve been to?

  7. What is the longest you’ve been away from home for?

  8. What is the longest flight you’ve taken?

  9. Do you plan and book your holidays yourself or do you get it done through a travel agency or third party agent?

  10. Have you ever lived in another country for an extended period of time? If so, where?

  11. What travel advice would you give to someone traveling internationally for the first time?

  12. What is the most trouble you’ve been in while traveling?

  13. Have you ever gotten scammed while in another country?

  14. Do you prefer to travel solo or as part of a group?

  15. Where would you like to go on vacation to?

  16. Where is the best place you have hiked in?

  17. Where do you prefer to stay? Hotel/hostel/apartment/couchsurfing?

  18. Have you explored a lot of your home country?

  19. What do you think is the biggest advantage of solo travel?

  20. Who is the most interesting person you’ve met during your travels?

  21. Have you ever missed a flight?

  22. Are you a member of any frequent flyer programs?

  23. Which place would you not visit again?

  24. If you speak more than one language, which language is the easiest and hardest to learn?

  25. What is your favorite museum?

  26. What is a typical meal like from your country?

  27. What travel apps you you use most often?

  28. How many passports have you gone through?

  29. What home food do you miss most when travelling abroad?

  30. Are there any aspects of a foreign culture that you will never get use to?

Speaking of a foreign culture.. Here are:
the most strange and exotic foods eaten across the world


Travel and exploring the world is my favorite past-time. But you already knew that, right? Here are travel questions to ask to get you talking about past vacations, favorite destinations, future travel aspirations, and bucket list places.

What to caption a travel photo?

Engaging and interesting Questions on Travel
  1. Where is the most amazing place you’ve encountered during your travels?

  2. Do you prefer to travel to famous and popular destinations or off the beaten track spots?

  3. How many photos are saved on your hard-drive in total?

  4. What is your favourite foreign cuisine?

  5. What is your favorite word for travel?

  6. What inspires you to travel?

  7. Do you usually bring back souvenirs for your trip?

  8. What travel quote do you live by?

  9. What country (or countries) would you like to visit the most?

  10. How many days until your next vacation?

  11. What place should everyone see at least once in their lifetime?

  12. Are there any popular places or destinations you’d like to avoid?

  13. What is the best place to visit in your own country?

  14. What are your favourite countries?

  15. Do you prefer novel stimulating experiences or a chilled out relaxed vacation?

  16. Do you keep a journal to document all your experiences exploring the world?

  17. What was the most recent road trip you took?

  18. What is your best-loved national park?

  19. What is your favourite tropical island?

  20. What is your favourite city for a weekend break?

  21. What is the most money you’ve spent on a plane ticket? Where’d you go?

  22. What is your favorite foreign dessert?

  23. Where was your first vacation with your family?

  24. What is your most prized travel possession?

  25. Which city has the best street food?

  26. What one place do you have to visit before you die?

  27. Are you planning on travelling again soon in a post pandemic world?

  28. Which country has the most beautiful flag?

  29. How does travel bring meaning to your life?

I’ve had a lot of misadventures and crazy travel experiences over the years.
Here are a couple of my misadventures


A simple format of intriguing and fun questions for traveling. Present these to your fellow travelers with these odd, funny, and interesting scenarios to get into some great conversations.

Map world Travel Questions
  1. Would you rather lose all your travel photos or all of your money?

  2. Would you rather travel back in time and meet your ancestors or forward in time to meet your descendants?

  3. Would you rather travel the world by plane, train, or ship?

  4. Would you rather see a lot of countries for a little bit or get to know one in-depth?

  5. Would you rather explore the deepest part of the ocean or outer space?

  6. Would you rather upgrade your flight to first class or your hotel room to the penthouse suite?

  7. Would you rather go hiking, visit museums, or to the beach?

  8. Would you rather be the last person left on earth, or be one of the first people on Mars but you’ll never come back home?

  9. Would you rather swim with dolphins or go shark cage diving?

  10. Would you rather be able to pause, rewind, or fast forward time?

  11. Would you rather only speak English or speak every language in the world except for English?

  12. Would you rather travel the whole world but never finding love or finding your soulmate but never being able to travel?

  13. Would you rather be able to speak all languages or be able to talk to animals?

  14. Would you rather explore the dessert heat of the Sahara or the icy landscape of Antarctica?

  15. Would you rather have the super power of teleportation or flying?

  16. Would you rather have a summer beach vacation or a winter mountain trip?

  17. Would you rather discover the jungle on an African safari or the sea on a cruise?

  18. Would you rather sleep in a room in a haunted hotel or filled with snakes?

  19. Would you rather walk the entire Great Wall of China or climb Mount Kilimanjaro?

  20. Would you rather live the life of a king alone or live like a nomad with your friends and family?

  21. Would you rather watch the rising sun or the setting sun?

  22. Would you rather go on lots of small trips or one long trip?

  23. Would you rather be able to tell your past self one thing or be able to ask your future self one question?

I hope you’ve appreciated this complete set of travel questions. I’ve included more than enough vacation questions to fuel those conversations with a traveler or while discovering the world.

What are some of your favorites? And did any of these reveal some insights or breakthroughs?

>> Read next:

Happy travelling!


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4 Responses

  1. Amber says:

    I love this site.
    Continue the good work!

  2. Addy says:

    This list is amazing! 💯

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