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Funny Icebreaker Questions for Vacations & Holidays

These Funny Icebreaker Questions are specifically targetted to people that you may encounter on a vacation. Don’t be shy to put yourself out there and say, Hey I have some interesting conversation questions - want to try one or two?”

Chances are your new travel buds wold be more than willing to participate. There are so many situations where we are stuck on tour buses, waiting to be picked up or just sitting by the pool that just beg for some interesting questions.

These Funny Icebreaker Questions will help you find a connection and/or have some fascinating conversations with perfect strangers. Make a list of the questions that intrigue and tuck into your suitcase before you leave.

Is this your first time here in _________?

Why did you choose this location as your vacation destination?

Weirdest thing you have ever eaten?

What would you do if you didn’t have to work?

What is your favorite activity to do on vacation?

What is your pet peeve when you are on vacation?

Who is the worst actor in Hollywood?

Who would you call for bail money?

Name a time when you got into big trouble with your parents.

What is the best meal you have ever had on vacation?

You wouldn’t be caught dead, where?

Do you have any hidden talents?

How far east can you go before you're heading west?

Name two things you consider yourself to be very good at.

Name two things you consider yourself to be very bad at.

Do you have any relatives in jail?

What countries have you travelled to?

Have you ever feared for your life while on vaction?

If you had to, what family member would you kill off and why?

Name one thing that not many people know about you.

Name 1 thing you miss about being on vacation as a kid.

When you were a kid, what did you want to be when you grew up?

What was your favorite childhood injury?

What is your worst travel experience?

Which is the best vacation you’ve ever had?

What is the craziest thing you have ever done?

What are you passionate about?

How much deeper do you think the ocean would be if sponges didn't grow in it?

What is your best customer service experience while on vacation?

What outdoor activities do you like to do?

If you could choose, how would you want to die?

If your house was on fire and you could grab only 3 things before leaving, what would they be?

Which is your most favorite place on this earth?

Where do you live and why do you like to live there?

Do you believe in extraterrestrials or life on other planets?
Do you believe in ghosts?

Can a short person "talk down" to a taller person?

How fast do hotcakes sell?

Do you have any phobias?

What do you think the greatest invention is in your lifetime and why?

What do you think the secret to a good life is?

What would be your dream job?

If you could have 1 wish granted, what would they be?

If you could live anywhere in the world, where would you live?

Name an exotic country that you would like to go to for a vacation?

What do people of China call their good plates?

Why do dogs like the smell of other dogs butts?

What crazy activities do you dream of trying someday?

If you could go on a road trip with any person
(dead or alive), who would you choose and where would you go?

If there's an exception to every rule, is there an exception to that rule?