How I'm Using AI to Plan My Southeast Asia Trip (November 2026)

Last year, I planned a Malaysia trip entirely with ChatGPT. It worked so well that I’m doing it again, but this time, I’m documenting the entire process in real-time.

The goal: Plan an epic November 2026 trip to either Japan, Vietnam, or Cambodia (or a combination) using every AI tool at my disposal.

The twist: I built my own AI flight search agent to find the best deals.

Follow along as I make decisions, find deals, and figure out where I’m actually going.

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The Starting Point

When: November 2026 (2-3 weeks) Who: Me and my partner Budget: Mid-range (~$150-200/day) Starting point: Europe Special needs: Gluten-free options (partner has celiac disease)

The candidates:

• 🇯🇵 Japan - Always dreamed of it, autumn colors
• 🇻🇳 Vietnam - Incredible food, good value
• 🇰🇭 Cambodia - Angkor Wat bucket list, beaches

I genuinely don’t know which to choose yet. Let’s let AI help decide.

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AI Tools I’m Using

Here’s the full toolkit for this planning process:

Tool	Role	Cost
ChatGPT (guide)	Destination comparison, itinerary drafting, decision frameworks	$20/mo (Plus)
Claude (vs ChatGPT)	Deep research, weighing trade-offs, writing packing lists	Free tier
Perplexity	Current conditions, traveler reviews, real-time info	Free
Custom Flight Agent	Daily price monitoring across routes	Self-hosted (build guide)
Google Flights	Cross-referencing AI flight suggestions	Free
Wanderlog	Visual itinerary mapping	Free tier

The combination of multiple AI tools is key. No single tool gets everything right, ChatGPT is great at big-picture planning, Perplexity excels at current, sourced information, and Claude is best for nuanced comparisons when I need to weigh competing priorities.

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Visa Requirements (AI-Researched)

Before diving into itineraries, I asked Perplexity to check visa requirements for German passport holders:

Destination	Visa Required?	Duration	Cost
Japan	No (visa-free)	Up to 90 days	Free
Vietnam	E-visa required	90 days single/multiple	~$25
Cambodia	Visa on arrival or e-visa	30 days	~$36

Japan is easiest, just show up. Vietnam’s e-visa process takes 3 business days online. Cambodia offers visa on arrival at airports, but the e-visa avoids queues.

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Phase 1: Initial Research (Current)

What I Asked the AI Tools

ChatGPT:

I'm planning a 2-3 week trip in November 2026.
Comparing Japan, Vietnam, and Cambodia.
Budget: $150-200/day for two people.
We love food, culture, and some beach time.
One of us has celiac disease (needs gluten-free options).

Compare these destinations for November travel.

Perplexity:

What's the weather like in Japan, Vietnam, and Cambodia in November?
Which is best for a 2-3 week trip?
Include recent traveler experiences.

My Flight Agent: Running daily searches for:

• Europe → Tokyo (NRT/HND)
• Europe → Hanoi (HAN) / Ho Chi Minh (SGN)
• Europe → Phnom Penh (PNH) / Siem Reap (REP)

Initial AI Analysis

Factor	Japan	Vietnam	Cambodia
November weather	Excellent (autumn)	Good (dry season starts)	Good (dry season)
Budget fit	Stretching it	Perfect	Perfect
Gluten-free ease	Good (rice-based)	Moderate	Challenging
Flight cost (est.)	$800-1200	$600-900	$700-1000
Wow factor	High	High	Very high (Angkor)

Early leaning: Vietnam or Cambodia offer better value, but Japan’s autumn is legendary…

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Phase 2: Flight Monitoring

This section updates as I track prices

Current Best Prices Found

Route	Price	Airline	Stops	Found via
BER → NRT	$---	---	---	Flight Agent
BER → HAN	$---	---	---	Flight Agent
BER → REP	$---	---	---	Flight Agent

Updating weekly as my flight agent runs

Price Trends

Chart coming as I collect more data

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Phase 3: Deep Dive Research

Japan in November

What AI told me:

• Autumn foliage peaks mid-November
• Kyoto gets extremely crowded
• Tokyo → Kyoto → Osaka is classic but busy
• Consider less touristy routes

Detailed guide: AI Trip Planning: Japan

Vietnam in November

What AI told me:

• North (Hanoi, Ha Long Bay): Cool, occasional drizzle
• Central (Hoi An, Hue): Tail end of rainy season
• South (Ho Chi Minh, Mekong): Dry season starting

Detailed guide: AI Trip Planning: Vietnam

Cambodia in November

What AI told me:

• Dry season begins
• Angkor Wat less crowded than December-February
• Can combine with southern beaches
• Consider adding Siem Reap + Koh Rong

Detailed guide: AI Trip Planning: Cambodia

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Phase 4: The Decision

Coming soon, currently gathering data

Decision Framework (AI-Assisted)

I asked Claude to help me build a decision matrix:

Help me decide between Japan, Vietnam, and Cambodia for November.
Weight these factors by importance to me:
- Unique experiences (high)
- Food scene (high)
- Budget fit (medium)
- Gluten-free ease (high)
- Weather (medium)
- Flight cost (medium)

Results: Updating as I refine

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Phase 5: Booking

Coming soon

What I’ll Book with AI Help

• Flights (via my flight agent alerts)
• Travel insurance (AI-researched coverage needs)
• Accommodation (ChatGPT recommendations + Agoda for Asia-specific deals)
• Key experiences (Perplexity research)
• Transport within destinations (Grab for Southeast Asia, Rome2rio for route options)
• Restaurant list (gluten-free focused)

Travel Insurance Research

I asked Perplexity to compare insurance needs for my three destination options:

Compare travel insurance requirements for Japan, Vietnam, and Cambodia.
What coverage is essential for each?
What activities need special coverage?
Evacuation coverage importance for each destination?

Result: Cambodia requires the most coverage (evacuation essential), Japan needs high medical coverage (expensive hospitals), Vietnam needs motorbike coverage if renting.

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Lessons Learned So Far

What’s Working

✅ Flight agent monitoring - Already seeing price patterns ✅ Perplexity for research - Great for current conditions ✅ ChatGPT for comparison - Good at weighing trade-offs

What’s Challenging

⚠️ Too many options - AI gives lots of ideas, hard to narrow down ⚠️ Conflicting advice - Different tools sometimes disagree ⚠️ Analysis paralysis - More data isn’t always better

Adjustments I’m Making

1. Setting a decision deadline (not endless research)
2. Trusting gut feelings alongside AI recommendations
3. Focusing on 2-3 key priorities, not optimizing everything

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Updates Log

[Date TBD] - Started planning, running initial comparisons [Date TBD] - Flight agent deployed, monitoring prices [Date TBD] - Next update

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Follow the Journey

I’ll update this article as I progress. Bookmark it or check back to see:

• Which destination I choose (and why)
• Best flight deals I find
• Final itinerary
• Post-trip review

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Related Guides

• My last AI-planned trip: Malaysia with ChatGPT
• Build your own flight agent: AI Flight Search Agent Tutorial
• Destination deep-dives:
  • AI Trip Planning: Japan
  • AI Trip Planning: Vietnam
  • AI Trip Planning: Cambodia
• Compare destinations: Japan vs Vietnam vs Cambodia