Want Better Trips? Answer This Anti-Boring Travel Questionnaire (No 'Beach or City?' Nonsense)

If you’ve ever been handed a trip planning form that asked 'beach or city?' and instantly blacked out from boredom, you’re not alone. The truth is, great travel isn’t built on yes-or-no boxes or vibe-less questions. It’s shaped by the little details that make you tick. How you eat, how you flirt with adventure, how you want to feel in your down time.

This travel questionnaire was designed to help clients and (maybe even other advisors too) ditch cookie-cutter vacations in favour of truly personalised travel planning. These ten questions cut past the clichés and get to the good stuff: the feelings, desires and sparks that build better itineraries.

Because anti-boring travel starts with asking the right questions (and I have got the questionnaire). The answers, what my clients say re-written in my voice.

The Anti-Boring Travel Questionnaire for Personalised Trips

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1. When you picture the you, you like the most, what are you wearing, holding, looking at?

What one client said..

'Linen trousers, bare feet, a glass of rum, watching the sun sink into the sea like it owes me money.'

Travel Match:

Round Hill Hotel & Villas, Jamaica – barefoot old Hollywood glam, golden hour magic and a rum menu to match your main-character energy. Read a little more here in my blog post on barefoot bliss and Caribbean cool.

2. What’s your idea of indulgence that doesn’t need an Instagram caption to matter?

What one client said...

'A breakfast I didn’t make, on a terrace no one else knows about. Bonus points if it’s raining softly.'

Travel Match:

Monteverdi Tuscany, Italy – an intimate hillside escape where even the silence feels intentional. Fresh grape and rosemary focaccia, misty mornings and zero need for filters.

3. Would you rather eat something that makes you close your eyes? Or sleep somewhere that makes you gasp when you wake up?

What one client said...

'Eat. If there’s a tasting menu, I want to be emotionally compromised by course five.'

Why This Travel Questionnaire and it's questions Builds Better, More Personalised Trips

Travel Match:

Mexico City – dinner at Pujol, mezcal that makes your soul shimmy and a stay at Casa Polanco. There, every corner is oozing of arty details.

4. How spicy do you like your experiences: hint of heat, tongue-tingling, or reckless decisions?

What one client said...

'Tongue-tingling. I want heartbeats, not heartburn.'

Travel Match:

Tokyo After Dark, with a private guide to hidden izakayas, jazz dens and whisky bars hidden down secret alleyways.

5. You wake up on your second morning somewhere new. What do you not want to see on the itinerary?

What one client said...

'A group tour. Or anything that requires matching lanyards.'

Travel Match:

A private sailing charter through the Greek Islands – slow mornings, secret beaches and a captain who knows the best dockside tavernas. No megaphones. Ever. Swipe for your Vikings and Exploras

6. What’s the weirdest, most wonderful detail you still remember from a past trip?

What one client said...

'A taxi driver in Morocco who made me smell his grandmother’s mint before we drove off.'

Travel Match:

El Fenn, Marrakech – bold, brilliant and full of stories. Tiles, textiles and serendipity around every corner.

7. Say someone books a trip just to seduce you, what would seal the deal?

What one client said...

'Candlelit courtyard, live acoustic guitar and wine that only a few know about.'

Travel Match:

Les Roches Rouges, Côte d’Azur – Minimalism, romanticism and barefoot Riviera cool. There's Poolside rosé and sea-salt breezes.

8. When the vibe hits just right, do you dance, go silent or order one more round?

What one client said...

'Silent. Not from boredom but from awe.'

Travel Match:

Wadi Rum, Jordan – stargazing from a desert dome, surrounded by Mars-like stillness. The kind of quiet that makes your heartbeat louder.

9. What place from a book, film or dream would you disappear into, if you could?

What one client said...

'The Italian villa from that one movie. You know the one... slow bike rides, stone walls, too much wine.'

Travel Match:

Puglia – trulli rooftops, olive groves and candlelit dinners in courtyards that say to you 'stay a while.'

10. What would make you pause mid-trip and say: 'This. This is exactly what I needed.’

What one client said...

'A stranger giving me directions and ending up sharing a bottle of wine together.'

Travel Match:

Lisbon, Portugal – slow hills, warm locals, soulful food and just enough magic to make strangers feel like characters in their own story.

Anti-boring travel questionnaire - individuality in travel planning

Thoughts

These aren’t just fun-to-answer questions.

They’re the difference between a trip that checks boxes and one that rewires your individual sense of self. If like myself you're a travel advisor wanting to go deeper with your clients, or a client who knows you deserve more than shuffleboard and sad salads, start here.

Because better trips don’t begin with a list. They begin with a feeling. And the right questions.

By the way, one of those answers were mine. Any guesses which one?

📍 Ready to travel better?

Want help planning your next trip around the real you? Reach out at oyitravel@outlook.com. Or start with my Mini Discerning Traveller guide to get you and the entire family inspired. Or take this questionnaire and turn it into your next unforgettable journey.