How I'm Using AI to Plan My Southeast Asia Trip (November 2026)
Follow along as I use ChatGPT, flight search agents, and AI tools to plan my next adventure to Japan, Vietnam, or Cambodia. Real-time updates included.
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.
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.
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.
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.
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…
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
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
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
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.
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
- Setting a decision deadline (not endless research)
- Trusting gut feelings alongside AI recommendations
- Focusing on 2-3 key priorities, not optimizing everything
Updates Log
[Date TBD] - Started planning, running initial comparisons [Date TBD] - Flight agent deployed, monitoring prices [Date TBD] - Next update
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
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
Related Articles
Build an AI Flight Search Agent (No Coding)
Learn how AI agents work by building a flight search assistant. From no-code tools to Python scripts, find the cheapest flights automatically.
Perplexity AI for Travel Research: Better Than Google?
Perplexity combines AI conversation with real-time search, making it perfect for travel research. Here's how to use it to plan smarter trips.
Google Gemini for Travel Planning: The Real-Time Advantage
Gemini's real-time data and Google integration make it uniquely powerful for travel planning. Here's how to use it effectively for your next trip.