Imported from gethouston/houston (store/agents/operations/.agents/skills/plan-a-trip/SKILL.md). Install upstream with npx skills add gethouston/houston --skill plan-a-trip. Copyright stays with the author.

Plan A Trip

When to use

• "I'm going to {city}" / "plan my travel to {X}" / "plan a trip end-to-end".
• "flights for {conference}" / "I have a customer visit in {X}".
• "assemble my trip pack".

Connections I need

I run external work through Composio. Before this skill runs I check the categories below are linked. Missing → I name the category, ask you to connect it from the Integrations tab, stop.

• Calendar (Google Calendar, Outlook) - Required. Lets me see existing meetings during the trip window and pull events at the destination.
• Inbox (Gmail, Outlook) - Optional. Helps me find existing booking confirmations or itineraries.
• Travel providers (flight or hotel search) - Optional. If connected I surface real options; otherwise I write search criteria and you book yourself.

If no calendar is connected I stop and ask you to connect your calendar first.

Information I need

I read your operations context first. For every required field that's missing I ask ONE plain-language question (best modality: connected app > file drop > URL > paste) and wait.

• Destination and dates - Required. Why I need it: nothing works without where and when. If missing I ask: "Where are you going and on what dates? A range works if you're still flexible."
• Trip purpose - Required. Why I need it: a customer visit, a conference, an offsite, and a personal trip each get different itineraries and packing lists. If missing I ask: "What's the purpose of the trip - customer visit, conference, offsite, or personal?"
• Travel preferences - Required. Why I need it: I draft against your real preferences instead of guessing. If missing I ask: "What are your travel defaults - preferred airline, seat, hotel chain, dietary needs, anything I should always include?"
• Your timezone - Optional. Why I need it: catches schedule conflicts during the trip window. If you don't have it I keep going with TBD using your operating context default.

Steps

1. Read context/operations-context.md. If missing/empty, stop. Ask user run set-up-my-ops-info first. Key-contacts + priorities anchor "what meetings while there?" section.

2. Clarify trip. Extract from message: destination(s), dates (or range), purpose (customer visit / conference / offsite / personal), traveling-with (solo / team). If dates or destination missing + material, ask ONE question.

3. Read travel prefs. Read config/travel-prefs.json. If missing/empty, ask ONE question: "What are your travel defaults - preferred airline, seat (aisle/window), hotel chain, dietary needs, accessibility?" Write answer to config/travel-prefs.json, continue.

4. Read schedule. Read config/schedule-preferences.json for timezone. Check calendar conflicts over trip window via composio search calendar (pull events from depart to return date).

5. Resolve travel connections. composio search travel → check connected travel providers (flight + hotel search). Note available categories. If none connected, proceed with search criteria only + note user books manually (no hardcoded provider assumption).

6. Generate trip id - {YYYY-MM-DD}-{dest-slug} (kebab-cased destination, e.g. 2026-05-12-sfo).

7. Write travel/{trip-id}/trip.md - summary doc. Structure:

   # Trip  -  {destination}, {dates}
   
   ## Purpose
   {1–2 lines  -  customer visit / conference / offsite / personal}
   
   ## Dates
   Depart {YYYY-MM-DD}  -  Return {YYYY-MM-DD} ({N nights})
   
   ## Destinations
   - {city}, {country/state}  -  {nights}
   
   ## Key meetings while there
   - {date}  -  {attendee or event}  -  prep: {ready | missing}
   - ... (pulled from connected calendar for events in the trip window)
   
   ## Open questions
   - {anything the user should clarify before booking}

8. Write travel/{trip-id}/itinerary.md. Structure:

   ## Flights
   
   ### Outbound
   - Search criteria: {origin} → {destination}, {date},
     {airline pref}, {seat pref}, {max stops}, {price ceiling if
     mentioned}
   - Candidate options (if a provider is connected): {list}
   
   ### Return
   - Search criteria: {dest} → {origin}, {date}, {same prefs}
   - Candidate options: {list}
   
   ## Hotels
   - Search criteria: {chain pref}, {nights}, {neighborhood near
     key meetings}, {price ceiling if mentioned}
   - Candidate options: {list}
   
   ## Ground transport
   - Airport → hotel → meetings
   - Preferred mode: {ride-share / rental / public}
   
   ## Pending bookings
   - [ ] Outbound flight
   - [ ] Return flight
   - [ ] Hotel
   - [ ] Ground transport

9. Write travel/{trip-id}/packing.md - checklist adapted to destination weather (best guess from destination + dates; note assumption), trip type (formal customer visit vs conference vs offsite - clothing differs), and config/travel-prefs.json (dietary, accessibility). Sections: ## Essentials, ## Work, ## Clothing, ## Health & toiletries, ## Destination-specific.

10. Atomic writes - *.tmp → rename per file.

11. Append to outputs.json with type: "travel-pack", status "draft" until user approves bookings.

12. Summarize to user. "Trip pack ready at travel/{trip-id}/. Want me to search flight options via {available-provider} once you confirm dates, or are you booking yourself? Also - should I block your calendar during the trip?"

Outputs

• travel/{trip-id}/trip.md
• travel/{trip-id}/itinerary.md
• travel/{trip-id}/packing.md
• Possibly written config/travel-prefs.json on first run
• Appends to outputs.json with type: "travel-pack".

What I never do

• Book flights, hotels, ground transport without explicit user approval on specific option.
• Charge any card.
• Commit to travel dates on your behalf.
• Invent destination event not on calendar or named by user.