The Ultimate List of 100 “Would You Rather” Road Trip Questions

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A road trip is a classic American adventure that is as much about the journey as the destination. And what better way to pass the time than by playing the timeless game of “would you rather?”

But not just any old “would you rather?” game – we’re talking about travel-themed “would you rathers” that will make you laugh, think, and maybe even cringe a little.

So buckle up and get ready for the 100 best “would you rather” questions to play on a road trip that have to do with travel.

Would You Rather…

1. Would you rather have to sit next to a crying baby on a long-haul flight or a chatty seatmate who won’t stop talking?

2. Would you rather visit a city known for its food or its nightlife?

3. Would you rather take a train ride through the mountains or along the coast?

4. Would you rather spend a week camping in the wilderness or staying in a luxury hotel?

5. Would you rather go on a hot air balloon ride or a helicopter tour?

6. Would you rather go on a road trip with your best friend or your significant other?

7. Would you rather spend a day at the beach or in the mountains?

8. Would you rather visit a famous landmark or a hidden gem?

9. Would you rather backpack through Europe or Southeast Asia?

10. Would you rather stay in a treehouse or a yurt?

11. Would you rather take a cruise or a road trip?

12. Would you rather stay in a haunted hotel or a hotel with no air conditioning?

13. Would you rather go on a safari or a whale watching tour?

14. Would you rather go on a solo trip or a group trip?

15. Would you rather stay in a hotel with a pool or a hotel with a rooftop bar?

16. Would you rather visit a place known for its beaches or its mountains?

17. Would you rather stay in a hostel or a bed and breakfast?

18. Would you rather go on a guided tour or explore on your own?

19. Would you rather go on a road trip in an RV or a classic car?

20. Would you rather visit a place known for its wine or its beer?

21. Would you rather go on a beach vacation or a ski vacation?

22. Would you rather stay in a cabin in the woods or a beach house?

23. Would you rather travel by train or by plane?

24. Would you rather go on a food tour or a cultural tour?

25. Would you rather visit a place with a hot climate or a cold climate?

26. Would you rather stay in a hotel with a view or a hotel with a spa?

27. Would you rather visit a place known for its museums or its art galleries?

28. Would you rather go on a cruise with unlimited drinks or unlimited food?

29. Would you rather go on a solo trip or a trip with your family?

30. Would you rather stay in a hotel with a private pool or a hotel with a private beach?

31. Would you rather visit a place known for its architecture or its natural beauty?

32. Would you rather go on a road trip with your dog or your cat?

33. Would you rather visit a place known for its history or its nightlife?

34. Would you rather stay in a hotel with a balcony or a hotel with a fireplace?

35. Would you rather visit a place with a lot of tourists or a place with very few tourists?

36. Would you rather stay in a hotel with a gym or a hotel with a spa?

37. Would you rather go on a cruise or a backpacking trip?

38. Would you rather visit a place known for its beaches or its lakes?

39. Would you rather stay in a hotel with a rooftop pool or a hotel with a rooftop bar?

40. Would you rather visit a place known for its street food or its fine dining?

41. Would you rather go on a road trip in a convertible or a camper van?

42. Would you rather stay in a hotel with a beachfront view or a mountain view?

43. Would you rather visit a place known for its festivals or its sports events?

44. Would you rather stay in a hotel with a hot tub or a hotel with a sauna?

45. Would you rather visit a place known for its shopping or its outdoor activities?

46. Would you rather go on a trip with a packed itinerary or a trip with a lot of free time?

47. Would you rather stay in a hotel with a jacuzzi tub or a hotel with a rain shower?

48. Would you rather visit a place known for its theme parks or its national parks?

49. Would you rather go on a road trip with your favorite celebrity or your favorite athlete?

50. Would you rather visit a place you’ve been dreaming about for years or discover a brand-new destination?

51. Would you rather go on a beach vacation in Hawaii or the Caribbean?

52. Would you rather stay in a hotel with a rooftop garden or a hotel with a rooftop pool?

53. Would you rather go on a solo trip to a new place or revisit a favorite destination with friends?

54. Would you rather travel by train or by bus?

55. Would you rather go on a trip with a strict budget or with no budget restrictions?

56. Would you rather go on a trip with your parents or your grandparents?

57. Would you rather go on a road trip with your significant other’s family or your own family?

58. Would you rather visit a place known for its deserts or its rainforests?

59. Would you rather stay in a hotel with a private beach or a hotel with a private island?

60. Would you rather visit a place known for its castles or its cathedrals?

61. Would you rather go on a trip to a place with a lot of history or a place with a lot of natural wonders?

62. Would you rather stay in a hotel with a balcony overlooking the ocean or a balcony overlooking the city skyline?

63. Would you rather visit a place known for its wineries or its breweries?

64. Would you rather go on a trip with a lot of outdoor activities or a lot of indoor activities?

65. Would you rather stay in a hotel with a fireplace or a hotel with a bathtub big enough for two?

66. Would you rather go on a trip to a place with a lot of museums or a lot of parks?

67. Would you rather stay in a hotel with a spa or a hotel with a fitness center?

68. Would you rather go on a trip to a place known for its beaches or its waterfalls?

69. Would you rather stay in a hotel with a view of the mountains or a view of the ocean?

70. Would you rather visit a place known for its music festivals or its film festivals?

71. Would you rather go on a trip to a place with a lot of wildlife or a place with a lot of nightlife?

72. Would you rather stay in a hotel with a pool or a hotel with a hot tub?

73. Would you rather visit a place known for its ancient ruins or its modern architecture?

74. Would you rather go on a trip to a place with a lot of art galleries or a lot of theaters?

75. Would you rather stay in a hotel with a private chef or a hotel with a private bartender?

76. Would you rather go on a trip to a place with a lot of beaches or a lot of mountains?

77. Would you rather stay in a hotel with a king-size bed or a hotel with a balcony overlooking the city?

78. Would you rather visit a place known for its cuisine or its wine?

79. Would you rather go on a trip to a place with a lot of amusement parks or a lot of national parks?

80. Would you rather stay in a hotel with a rooftop pool or a hotel with a rooftop bar?

81. Would you rather visit a place known for its street art or its museums?

82. Would you rather go on a trip with your significant other or your best friend?

83. Would you rather stay in a hotel with a private cinema or a hotel with a private spa?

84. Would you rather visit a place known for its fashion or its history?

85. Would you rather go on a trip to a place with a lot of beaches or a lot of lakes?

86. Would you rather stay in a hotel with a sauna or a hotel with a steam room?

87. Would you rather visit a place known for its natural hot springs or its ski resorts?

88. Would you rather go on a trip to a place with a lot of temples or a lot of churches?

89. Would you rather stay in a hotel with a rooftop restaurant or a hotel with a rooftop pool?

90. Would you rather visit a place known for its coffee or its tea?

91. Would you rather go on a trip to a place with a lot of waterfalls or a lot of glaciers?

92. Would you rather stay in a hotel with a private garden or a hotel with a private beach?

93. Would you rather visit a place known for its mountains or its volcanoes?

94. Would you rather go on a trip to a place with a lot of markets or a lot of malls?

95. Would you rather stay in a hotel with a private helicopter pad or a hotel with a private yacht?

96. Would you rather visit a place known for its water sports or its winter sports?

97. Would you rather go on a trip to a place with a lot of lakes or a lot of rivers?

98. Would you rather stay in a hotel with a private chef or a hotel with a private masseuse?

99. Would you rather visit a place known for its hot air balloons or its paragliding?

100. And finally, would you rather visit a place known for its sunrises or its sunsets?

Phew, there you have it – 100 “would you rathers” for your next road trip. Grab some snacks, hit the road, and get ready for some lively debates with your travel buddies!

This article was produced by Our Woven Journey. Featured Image Credit: Deposit Photos.

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Karee Blunt is a nationally syndicated travel journalist, focused on discovering destinations and experiences that captivate and inspire others through her writing. She is also the founder of Our Woven Journey, a travel site focused on inspiring others to create memory-making adventures with their loved ones. Karee is passionate about encouraging others to step out of their comfort zone and live the life they dream of. She is the mother of six kids, including four through adoption, and lives with her family in the Pacific Northwest. You can learn more about Karee on her about me page.