Guided trip planning workflow. Asks destination, dates, travelers, class, and flexibility, then runs parallel flight/hotel search with cpp math and booking plan.
SkillScore73Maintained
On-demandOn-demand: invoked explicitly — never occupies your agent's context until called.
◆Personal Assistant pack
Last verified 8/16/2026
What it changes
Passed 16 of 22 test cases with the skill, and 11 of 22 without it.
Without skill50%
With skill73%
Checks it passed that the model alone missed
The response asks at most one single preliminary question.
The winning option justification consists of a single sentence.
The comparison table includes a dedicated column for cents-per-point valuation.
and 3 more in the full report
6 fixed10 passed either way5 still failing1 broke
Pass-rate lift
+23 pp
Tokens
+37%
Agent turns
0%
Response time
-22%
Model gemini-3.6-flashMeasured 8/16/2026v116 of 22 cases passed with skill
Tokens, turns and time describe resource use, not a dollar price.
See it in action
One of 6 test cases the skill fixed. Same model, same prompt, with and without the skill.
1 of 6
Prompt
Can you help us plan a flight itinerary for a 7-night anniversary trip to London next spring? Ask whatever questions you need to gather my preferences, evaluate points redemptions alongside cash pricing, show the math in a clear markdown table with co-pay and point valuation metrics, pick a clear winner, and provide concrete booking next steps.
What was checked, without and with the skill
Checked
Without skill
With skill
The response asks at most one single preliminary question.
Missed
Passed
case-03 · gemini-3.6-flash · 8/16/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md57 linessingle file
Plan Trip Skill
The user invoked this skill explicitly. Run a guided trip planning workflow that produces a concrete, opinionated recommendation with cents-per-point math, transfer paths, and a booking plan.
How to run this
If the user already gave details in their prompt arguments, use those. Otherwise, ask in this order, one question at a time. Don't fire all the questions at once.
Where? Destination(s). Accept regions ("Scandinavia"), cities ("Tokyo"), or specific airports.
When? Departure month or date range. Note flexibility: "exact dates" vs "any week in March" matters a lot for award availability.
Who? Number of travelers, ages if children/infants. The toolkit supports infant pricing and seat configurations.
What class? Economy / premium economy / business / first. Default to economy if unstated.
Trip length? Number of nights at destination if applicable.
Points or cash? Three valid answers: "best of both" (default), "points only" (treat cash as last resort), "cash only" (skip award search).
After question 6, confirm the plan back to the user in one sentence and start the workflow.
The workflow
Once you have the inputs:
Load lessons-learned first. Non-optional. Other skills depend on it.
Load flight-search-strategy for the canonical parallel search plan.
Pull balances via the awardwallet skill if the user's intent is points or "best of both" AND if balances aren't already in this session's context. Skip the pull if you already know them.
Run cash search in parallel via duffel, ignav, google-flights, and the relevant free MCPs (Skiplagged, Kiwi).
Run award search in parallel via seats-aero across ALL programs (never filter to one program upfront — see lessons-learned).
Cross-reference with transfer-partners and transfer-bonuses to find the cheapest currency you actually have.
Apply points-valuations to compute cents-per-point on each award option.
Surface anything from award-sweet-spots that matches this route.
Check stopovers if the destination involves a connection. Multi-city trips might unlock "two destinations for the price of one" via Aeroplan, Alaska, or Flying Blue.
Show the math in a markdown table. One row per option, ranked. Columns: program, miles cost, cash co-pay, total $ value, cpp, hold-before-transfer rule, recommendation.
Pick a winner with one-sentence reasoning.
Show booking next steps via booking-guidance: which program to call, hold rules, transfer timing, phone numbers if needed.
Hotels and ground transit
If the trip is more than just flights, mention these as available next steps in your closing summary (not as a question):
Hotels via compare-hotels (FHR/THC/Edit/Booking/Trivago/Airbnb/TaW)
Stopover side trips via stopovers + the relevant transit skill (scandinavia-transit for Norway/Sweden/Denmark, deutsche-bahn for Germany / Austria / Switzerland / Netherlands / France / Belgium)
Atlas Obscura suggestions for unique places at the destination
Round-the-world, Circle Pacific, and distance-based award products across alliances. Covers Star Alliance RTW, oneworld Explorer, Lufthansa M&M, Qantas, Cathay, JAL, Aeroplan, and Iberia charts.