Claude AI
The free tier handles every prompt in this guide. Claude Pro ($20/mo) mainly buys you higher usage limits and the full 200k context window, useful if you're planning a multi-city trip in one long conversation instead of starting fresh each time.
Key Features:
- ✓200k token context window on Pro (holds an entire multi-city trip in one conversation)
- ✓No real-time web access on the standard tier, so prices and availability are always estimates
- ✓Long, structured outputs without truncation, good fit for full itineraries
- ✓Follow-up questions stay in context, so you can revise a plan without re-explaining your trip
Pricing:
Free / Claude Pro $20/mo
Pros:
- + Free tier is enough for a single trip start to finish
- + Handles long, multi-part prompts (a full week itinerary in one go) without losing structure
- + Better at admitting uncertainty on prices/hours than confidently guessing wrong
Cons:
- - Cannot book anything or check real-time prices, availability, or flight status
- - Knowledge cutoff means very recent openings, closures, or visa rule changes need a manual double-check
- - No maps or live location awareness, so distances and walk times are estimates, not measurements
Best For:
Travelers who want a real planning conversation, not a form, and who will verify prices and bookings separately before paying for anything.

