Destination Research and Decision Making

From Lesson 1

Remember the difference between generic and contextual prompts? In this lesson, you’ll apply that principle specifically to destination research–getting AI to give you the kind of insider knowledge that used to require reading 15 travel blogs and three Reddit threads.

The Tourist Trap Problem

Here’s what happens when most people research destinations: they Google “best places to visit in [country],” get the same 10 listicle results everyone else sees, and end up at the same overcrowded spots that every other tourist visits.

The result? You fly halfway around the world to stand in a line for two hours, take the same photo everyone else took, and wonder why the trip didn’t feel special.

AI can break you out of this cycle–if you ask the right questions.

By the end of this lesson, you’ll be able to:

• Get honest, balanced destination assessments from AI
• Compare multiple destinations against your personal criteria
• Discover local experiences that most tourists miss
• Research seasonal patterns and optimal timing

Getting Honest Destination Intel

The secret to great destination research is asking AI to be a honest advisor, not a tourism promoter. Here’s how:

The Balanced Assessment Prompt

“Give me an honest assessment of [destination] for a [your travel style] traveler. Include:

1. The highlights: What genuinely makes this place special
2. The downsides: What will frustrate or disappoint most visitors
3. Who should go: The ideal traveler for this destination
4. Who should skip it: Who would be disappointed
5. Best time to visit: And why
6. Worst time to visit: And what happens if you go anyway
7. Budget reality check: What things actually cost (not just hotel prices)
8. The thing most travel blogs won’t tell you: One honest insight”

This prompt works because it explicitly asks for the negatives. Most AI responses default to being positive and enthusiastic. By asking for downsides and “who should skip it,” you force more balanced output.

Example output snippet for Bali:

Who should skip it: If you hate humidity, get stressed by aggressive street vendors, or want a quiet beach experience, Bali will frustrate you. The famous beaches (Kuta, Seminyak) are crowded and the water isn’t as crystal-clear as photos suggest. If that’s your ideal trip, consider the Philippines or Maldives instead.

The thing most travel blogs won’t tell you: Bali traffic is genuinely awful. A trip that looks like 20 minutes on Google Maps can take 90 minutes during peak hours. Base your accommodation decision on proximity to your main activities, not just the hotel quality.

That kind of honesty saves you from disappointment.

Going Deeper: The Local Expert Prompt

Once you’ve decided on a destination, dig deeper:

“You’re a local who has lived in [destination] for 10 years and loves showing friends around. My interests are [list interests]. I have [X days] and I’m visiting in [month].

Tell me:

• The neighborhoods tourists overlook but locals love
• Your personal favorite restaurants (specific names, what to order)
• The experience you’d recommend that isn’t in any guidebook
• The tourist trap that isn’t worth the hype (and what to do instead)
• The one logistical tip that saves hours of frustration”

Quick check: Think of a destination you’re curious about. Try the balanced assessment prompt right now. Were you surprised by any of the downsides mentioned?

Comparing Destinations: The Decision Matrix

Can’t decide between two or three destinations? Instead of agonizing, let AI build you a decision matrix.

The Comparison Prompt

“I’m trying to decide between [Destination A], [Destination B], and [Destination C] for a [duration] trip in [month/season]. Here’s what matters to me, ranked by importance:

1. [Most important factor, e.g., food scene]
2. [Second factor, e.g., budget-friendliness]
3. [Third factor, e.g., safety for solo travelers]
4. [Fourth factor, e.g., weather in my travel dates]
5. [Fifth factor, e.g., ease of getting around]

Create a comparison table rating each destination 1-5 on each factor, with a brief explanation for each rating. Then give me your overall recommendation and why.”

This works brilliantly because it forces a structured evaluation instead of vague “they’re all great!” responses. You’ll get something like:

Now you have a clear, personalized comparison instead of a gut feeling.

Seasonal Intelligence

Timing can make or break a trip. Use AI to understand the full picture:

The Seasonal Deep-Dive

“For [destination] in [month], tell me:

• Weather: Average temperatures, rainfall, what to actually expect day-to-day
• Crowds: Tourist density compared to peak season (as a percentage)
• Prices: How accommodation and flight costs compare to peak season
• What’s open/closed: Any seasonal closures, festivals, or special events
• Local mood: How locals feel about tourists during this period
• The trade-off: What I gain and what I sacrifice by visiting at this time

Be honest–if this is a bad time to visit, tell me that directly and suggest a better month.”

This is especially valuable for shoulder-season travel, where you might get 80% of the peak-season experience at 50% of the cost.

Researching Specific Interests

Generic destination research misses your specific interests. Use targeted prompts:

For Food-Focused Travelers

“I’m a serious foodie visiting [destination] for [X days]. I care more about authentic local food than Michelin stars. Tell me: the one food market I can’t miss, three restaurants where locals actually eat (not tourist traps), the regional specialty I should try even if it sounds weird, and the food neighborhood I should base myself in.”

For History and Culture Travelers

“I’m a history enthusiast visiting [destination]. Beyond the major museums and landmarks, what are the lesser-known historical sites that tell a more interesting story? I’d rather see a small, uncrowded Roman ruin than wait in line at the Colosseum.”

For Adventure Travelers

“I’m looking for outdoor adventures in [destination] that go beyond the typical tourist activities. I’m an intermediate-level [hiker/diver/cyclist]. What experiences would challenge me without being dangerous? Include any permits or guides I’d need to arrange in advance.”

The Research-to-Decision Pipeline

Here’s the workflow that brings it all together:

1. Cast a wide net: Use the balanced assessment prompt for 3-5 potential destinations
2. Compare: Build a decision matrix based on YOUR priorities
3. Validate timing: Do a seasonal deep-dive for your preferred dates
4. Go deep: Research your specific interests at the top destination
5. Gut check: Ask AI “What’s the one thing that might make me regret choosing this destination?”

That last question is powerful. It surfaces concerns you might not have thought to ask about–visa complications, altitude issues, language barriers, political situations, or cultural norms that might affect your experience.

Key Takeaways

• Ask for honest assessments with downsides, not just highlight reels
• Use a structured comparison matrix ranked by YOUR priorities to decide between destinations
• Research seasonal trade-offs to pick the right time, not just the cheapest time
• Go deep on your specific interests rather than following generic “top 10” lists
• Always do a gut check by asking about potential regrets

Up Next

In Lesson 3, you’ll take your chosen destination and turn it into a detailed, day-by-day itinerary. You’ll learn how to balance must-see attractions with spontaneous discovery, optimize travel time between locations, and build in the right amount of flexibility. This is where planning gets exciting.