101 This or That Travel Questions – Dreaming of sun-soaked beaches or majestic mountain peaks, but can’t decide where to go on your next vacation? With so many options to pick from these days, planning a trip can feel like one big game of ‘this or that.’ Beach or mountains? Guided tour or wander on your own? To help you zero in on the details that matter most, we’ve put together a list of 101 fun ‘this or that’ travel scenarios.

the best 101 this or that travel questions

As you imagine choices like lounging poolside at a resort versus backpacking around Europe, you’ll gain clarity on your ideal getaway. Work through questions about destinations, activities, packing strategies, and more. Whether you love luxury pampering or rugged adventures, iconic sights or hidden gems, this list has you covered. Get inspired for your upcoming travels and discover what excites you by reviewing these playful vacay ‘this or that’ questions. Happy planning!

101 This or That Travel Questions

Here are the first 50 “this or that” travel questions:

  1. Beach vacation or mountain getaway?
  2. Road trip or flying?
  3. Stay in a hotel or an Airbnb?
  4. Visit famous landmarks or explore lesser known areas?
  5. Pack light or bring everything you might need?
  6. Schedule activities ahead of time or play it by ear?
  7. Guided tour or explore on your own?
  8. Splurge on luxury or budget travel?
  9. Relax and recharge or full itinerary and activities?
  10. Travel solo or with friends/family?
  11. Tropical or cold weather destination?
  12. Hiking or water activities?
  13. Big city or small town?
  14. All-inclusive resort or independent travel?
  15. Camping or glamping?
  16. Rent a car or use public transportation?
  17. Foodie exploration or just eat whatever’s convenient?
  18. Nightlife and parties or early to bed?
  19. Visit popular tourist sights or hidden local gems?
  20. Lounge at the pool/beach or full day of sightseeing?
  21. International or domestic trip?
  22. Cruise ship or land travel?
  23. Pack snacks/food or eat out when traveling?
  24. Window seat or aisle seat on the plane?
  25. Early morning or late night flight?
  26. Carry-on only or check bags?
  27. Book everything ahead of time or play it by ear?
  28. Follow an itinerary or go with the flow?
  29. Luxury first-class tickets or cheap economy seats?
  30. Fly direct or save money with a layover?
  31. Stay up late or get up early to explore?
  32. Splurge on expensive activities or budget friendly free options?
  33. Lounge at a cafe or dine at Michelin star restaurants?
  34. Treat yourself to spa days or fill every day with activities?
  35. Visit main attractions or wander side streets?
  36. Do an intense multi-country trip or relax in one place?
  37. Stay connected or unplug from technology?
  38. Book private tours or small group excursions?
  39. Photography or keep experiences in the moment?
  40. Overschedule days or have plenty of downtime?
  41. History and culture or thrills and adventure?
  42. Guided experience or navigate on your own terms?
  43. Splurge on luxury or budget conscious?
  44. Lounge by the water or hike to mountain peaks?
  45. Foodie exploration or just grab quick bites?
  46. Early morning sightseeing or enjoy sunsets and nightlife?
  47. Highly active vacation or total relaxation?
  48. Stay in the heart of the action or secluded hideaway?
  49. Pack just essentials or overpack?
  50. Slow travel to immerse in one place or fast paced to see more?

Here are 51 more unique “this or that” travel questions to give you 101 total:

  1. Visit famous museums or smaller galleries?
  2. Guided bus tour or walking tour?
  3. Book popular tourist activities or find local hidden gems?
  4. Stay connected with WiFi or unplug from technology?
  5. Grab fast food or dine at white tablecloth restaurants?
  6. Splurge on first class flights or save with budget economy seats?
  7. Hostel dormitory or luxury hotel room?
  8. Public transportation or rent a car?
  9. Scenic train ride or domestic flight?
  10. Pack a whole suitcase or travel light?
  11. Stay in the city center or a quiet neighborhood?
  12. Visit sites alone or join a group tour?
  13. Follow a set itinerary or wing it?
  14. Wake up early or sleep in on vacation?
  15. Splurge on excursions or free activities?
  16. Guided tour or self-guided exploring?
  17. Lounge at the hotel pool or explore all day?
  18. Pack lots of outfits or minimal versatile clothes?
  19. Book everything ahead or schedule day-of?
  20. Share accommodations with others or private room?
  21. Luxury pampering or rugged outdoor adventures?
  22. Visit lively cities or quiet countryside?
  23. Indulge in local cuisine or quick, cheap eats?
  24. Rush between sights or slow travel immersion?
  25. Snap lots of photos or be in the moment?
  26. Unwind at a spa or sweat on a hike?
  27. Camping or 5-star hotel?
  28. Drive or fly to your destination?
  29. Visit tourist hot spots or undiscovered areas?
  30. Follow tips from locals or a guidebook?
  31. Early bird or night owl sightseeing?
  32. Pack books/games or electronics for entertainment?
  33. Guided experience or explore independently?
  34. Lively nightlife or peaceful retreat?
  35. High-end shopping or local markets?
  36. Adventure activities or total relaxation?
  37. Urban exploration or beach/mountain escape?
  38. Independent or group tour?
  39. Luxury cruise or budget sailboat?
  40. Visit iconic landmarks or hidden local spots?
  41. Hotel loyalty program or comparison shop rates?
  42. Research deeply or minimal advance planning?
  43. Highly active or mostly relaxing itinerary?
  44. Comfortable shoes or stylish outfits?
  45. Backpack or rolling suitcase?
  46. Sightseeing or spa days?
  47. Fly or take a train?
  48. Pack light or overpack?
  49. Guided tour or self-guided visit?
  50. Off the beaten path or famous sights?
  51. Splurge on experiences or budget conscious?

This or That Travel Ideas and Tips

Here are some ideas for creative and lesser known ways to play and utilize “This or That” travel questions:

  • Turn it into a travel vision board/collage – Cut out or print pictures of different destinations or travel styles and paste them on a board. Move the options around as you answer the “this or that” questions to visualize your preferences.
  • Travel journal brainstorming – Write out some of the key “this or that” questions in your travel journal. Freewrite on the pros and cons, your gut reactions, memories associated with the choices to tap into your travel wishes.
  • Research inspiration – If you’re undecided between two options, use the questions as a launchpad for researching each choice more in-depth to learn the pros and cons.
  • Solo travel decision making – When traveling solo, use the questions as a handy tool to make decisions “in the moment” when you reach a fork in the road.
  • Couples/group travel compromise – Have each person answer independently, then compare to find options that appeal to everyone.
  • Travel bag/packing list – Answer the questions about packing light vs overpacking, types of clothes, etc and make a list of exactly what to bring.
  • Personality quiz – Have friends/family do the quiz to reveal more about their travel style personalities. Compare results.
  • Future travel wish list – Save the list and periodically re-answer to track how your preferences evolve over time.
  • Jumpstart conversations – Use the thought-provoking scenarios to spark deeper conversations about why certain options appeal more.
  • Anticipation building – Slowly read through the questions, imagining each scenario, to get excited and build trip anticipation.
  • Destination generator – Assign a number to options you’re considering, then use a random number generator to “decide” your next destination or activity.

The Benefits of “This or That” Travel Planning

  • Helps narrow down options and make decisions
  • Gets you thinking about priorities and preferences
  • Sparks inspiration and anticipation for future trips
  • Fun way to daydream and visualize different scenarios
  • Creates a framework to compromise if traveling with others
  • Provides guidance when deciding things spontaneously during a trip

Additional Tips for Using “This or That” Questions for Trip Planning

  • Be open minded – don’t just default to your usual style
  • Think aspirational – would you prefer a more active or relaxing trip right now?
  • Consider weather, season and companions – some options work better in certain contexts
  • Focus on gut reactions – go with what sparks joy and excitement
  • Do some research if you’re undecided on a scenario to learn more
  • Save your responses to track how your preferences change over time

Bonus “This or That” Travel Topics to Inspire You

  • National parks or big cities
  • Road trip or cross-country train
  • Travel photography or enjoying the moment
  • Trying local cuisine or cooking in an Airbnb
  • Hiking trails or wine tasting tours
  • Living out of a suitcase or settling in one spot
  • Luxury pampering or cultural immersion

Hope this gives you some additional ideas to use in your travel planning or getting to know your travel buddies even better.

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