Purpose
Turn a set of destinations, meetings, and preferences into a single door-to-door itinerary that accounts for timezones, transfer buffers, meeting sequencing, and failure points — so the executive always knows exactly where to be, when, and what happens if something slips.
When to Use
Invoke this skill when the user asks to:
- Plan a multi-city business trip for an executive
- Build a travel itinerary spanning multiple timezones
- Sequence meetings across cities and align them with flights and hotels
- Coordinate ground transport, hotel check-ins, and meeting prep into one plan
- Create a contingency-ready travel document for a C-suite leader
- Fix a trip where meetings and travel connections are colliding
Inputs Required
Before starting, collect:
- Cities and dates: Ordered list of destinations with arrival/departure dates
- Confirmed meetings: For each — company/person, city, date, fixed vs. flexible time, expected duration
- Departure origin & home timezone: Where the trip starts and the executive's base timezone
- Flight preferences: Airline/alliance loyalty, cabin class, preferred departure windows, red-eye tolerance
- Hotel preferences: Loyalty program, proximity priority (near meetings vs. airport), room requirements
- Ground transport preferences: Car service vs. rideshare vs. rental, and any standing vendor accounts
- Executive constraints: No-fly windows, dietary needs, energy/pacing preferences (e.g., no meetings within 90 min of landing), personal commitments
If flight or hotel preferences are missing, default to the executive's stated loyalty programs and a 60-minute meeting-to-transfer buffer, and flag the assumption at the top of the itinerary.
Instructions
Step 1: Build the Timezone & Sequence Map
Before scheduling anything, establish the trip's skeleton.
- List each city with its UTC offset and the local time relative to the home timezone.
- Order cities to minimize backtracking and jet-lag disruption — prefer traveling west-to-east or grouping same-timezone cities where meeting dates allow.
- For each fixed meeting, mark it as an immovable anchor. Everything else schedules around anchors.
- Flag any date/timezone conflict where a confirmed meeting cannot be reached given travel time (e.g., a morning meeting the day after a red-eye that lands after it starts).
Step 2: Lock Flights Around Anchors
For each city-to-city leg:
- Recommend a specific flight window (not an exact flight unless one is given): departure time, arrival time, and duration in both home and local time.
- Apply arrival buffers: minimum 90 minutes gate-to-curb for international, 45 minutes domestic before any transfer commitment.
- Never schedule a meeting within the executive's stated post-landing recovery window (default 90 minutes for same-timezone, 3 hours after crossing 3+ timezones).
- Note passport/visa/customs implications for international legs and lounge availability for long layovers.
Step 3: Sequence Ground Transport
For every transition point (airport→hotel, hotel→meeting, meeting→meeting, hotel→airport):
- Specify the transport mode, estimated door-to-door time, and a buffer.
- Use realistic city-specific transit assumptions (peak-hour traffic, distance from airport to CBD).
- Add a 15-minute curb buffer to every car-service pickup and a 30-minute earlier-than-needed rule for airport departures.
- Bundle same-day meetings geographically so ground transport isn't crisscrossing the city.
Step 4: Assign Hotels
For each overnight city:
- Recommend a hotel positioned by the stated priority (nearest most meetings, or nearest airport for short stops).
- Confirm check-in/check-out times against arrival/departure — flag any early-arrival gap and recommend early check-in or day-use.
- Note the walking/driving time from the hotel to the first meeting of the next day.
Step 5: Sequence Meeting Prep
Insert prep blocks, not just meetings.
- Before each meeting, add a prep window (default 30 minutes) with a one-line note of what to review.
- For back-to-back meetings, add a 15-minute reset/transition block.
- Identify any meeting where the executive lands the same day and flag whether prep time realistically exists.
Step 6: Build the Contingency Layer
For each high-risk point (tight connections, single-flight-of-the-day legs, weather-prone routes):
- Note the risk and the fallback (next available flight, alternate meeting time, backup car vendor).
- Provide one "if the first flight cancels" alternate path per critical leg.
- List a single point-of-contact/confirmation number line for flights, hotels, and car service.
Output Format
- Structure: One master document, organized chronologically by day, each day headed with date and city; all times shown in local time with home-timezone in parentheses
- Length: Scales with trip; typically 700–1,400 words for a 3–5 city trip
- Format: Structured document — a summary block at top, then day-by-day timeline blocks, then a contingency appendix
- Sections: Trip Summary & Assumptions → Timezone Map → Day-by-Day Itinerary (flights, transport, hotel, meetings, prep) → Contingency Appendix → Confirmation Reference List
- Tone: Precise, calm, and directive — written so the executive reads one line and knows the next action; no hedging
Quality Checklist
Before delivering output, verify:
- [ ] Every meeting is reachable given the flight and transfer times before it (no impossible connections)
- [ ] All times display in both local and home timezone
- [ ] Every transition (airport, hotel, meeting) has an assigned transport mode and buffer
- [ ] No meeting falls inside the executive's stated post-landing recovery window
- [ ] Each overnight city has a hotel with check-in/out reconciled against arrival/departure
- [ ] Every critical flight leg has a named fallback in the contingency appendix
Notes
- The most common failure is under-buffering ground transport in unfamiliar cities — when uncertain, add time rather than trim it.
- If a meeting anchor makes the whole sequence infeasible, surface that immediately at the top of the summary rather than silently forcing a tight connection.
- Red-eyes save days but cost the next morning; only recommend one if the executive's pacing preferences allow, and never stack a red-eye against a same-morning meeting.
- Keep confirmation numbers and vendor contacts in one appendix block so the executive never hunts across the document mid-transit.
How to use this skill
This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.
Installing in Claude Code:
~/.claude/skills/<folder-name>/SKILL.md— auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)<your-project>/.claude/skills/<folder-name>/SKILL.md— auto-loads only when working in that project (recommended for project-specific skills)
Restart Claude Code or open a new session to register.
Using in Claude.ai, ChatGPT, Gemini, or other AI tools:
- Drag this file into a new chat, or copy and paste its contents
- Send your task or request as your next message — the AI will apply the skill where it fits
For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills