Travel Planning

• Each day should usually have one main area / route spine.
• Night activities should fit the area already being visited where possible.

Use this skill when

• Planning a multi-day trip
• Building a city itinerary
• Updating an existing itinerary with hotel / flight / reservation changes
• Reorganizing routes to be more geographically sensible
• Turning a messy plan into a polished final version
• Writing itinerary notes into Notion or another notes system

Workflow

1. Identify fixed inputs:

   • destination
   • dates
   • hotel
   • transport constraints
   • reservation anchors
   • arrival/departure times
   • explicit dislikes / exclusions

2. Build a simple map in your head first:

   • near hotel
   • east/west/north/south zones
   • far-out day-trip candidates
   • nightlife / dinner clusters

3. Lay out the trip day by day:

   • arrival day: light
   • full days: one main area per day
   • departure day: conservative

4. Sanity-check geography:

   • Is any day obviously zig-zagging?
   • Is any day too dense?
   • Are late-night returns realistic?
   • Are restaurant reservations fighting the route?

5. Add transport guidance:

   • MRT / subway when it is the most practical
   • rideshare when it meaningfully reduces friction
   • call out when a destination is too far for a casual add-on

6. Add practical meal structure:

   • don’t overload heavy meals before a booked dinner
   • use cafes / brunch / snacks to support pacing

7. Present the plan cleanly.

8. If asked to refine, re-synthesize instead of only appending fragmented edits.

Heuristics

Arrival day

• Keep it near the hotel or one easy evening activity.
• If landing late afternoon or evening, do not pretend a full sightseeing block is realistic.

Departure day

• Be conservative.
• Avoid far-out destinations.
• Work backward from airport arrival time.

Day trips

• Treat them as their own day whenever possible.
• If a destination is outside the city core, assume it competes with everything else that day.

Reservations

• A booked dinner is a hard anchor.
• Build the daytime route around it.
• Do not leave a fancy dinner stranded after an exhausting cross-city day unless unavoidable.

Hotel-centered planning

• Use the hotel area for:
  • arrival night
  • recovery windows
  • departure day
  • optional fallback dining

Output style

Prefer a structure like:

• short summary of the trip logic
• day-by-day itinerary
• transport notes
• rationale for why the route is geographically sensible
• optional “if you want to refine further” section

For polished final notes, produce a clean itinerary that reads like something the user could directly follow.

When writing a refined final version

Include:

• the fixed constraints that shaped the itinerary
• the final day-by-day route
• simplified transport choices
• explicit note when a place was removed because it was too far / too rushed / not worth it

Avoid

• attraction stuffing
• route zig-zagging
• mixing multiple distant districts into one day without explanation
• pretending arrival/departure days are full sightseeing days
• keeping outdated preferences in the plan after the user has changed them
• appending patch after patch when a clean rewrite is more useful

Good signs

A good travel plan should feel like:

• “yeah, this is how we’d actually do it”
• not: “this looks optimized by someone who has never physically moved through the city”