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/trip-planner

Full trip planning orchestration. Combines flight search, hotel search, and points optimization into one cost analysis. Use when the user says "plan a trip" or wants the complete picture for a destination.

BOOST
From plugin
travel-hacker
69748 skills1 agent6 MCP
Install
$ npx -y skills add borski/travel-hacking-toolkit --skill trip-planner --agent claude-code

How it fires

How this skill gets triggered: by you, by Claude, or both.

  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
  • You can call itInvoke it directly when you want it.
  • Slash command/trip-planner

Context preview

The summary Claude sees to decide when to auto-load this skill.

Full trip planning orchestration. Combines flight search, hotel search, and points optimization into one cost analysis. Use when the user says "plan a trip" or wants the complete picture for a destination.

SKILL.md

trip-planner.SKILL.md
name: trip-planner
description: Full trip planning orchestration. Combines flight search, hotel search, and points optimization into one cost analysis. Use when the user says "plan a trip" or wants the complete picture for a destination.
category: orchestration
summary: Full trip planning. Flights + hotels + points in one shot.
api_key: Uses individual skill keys

**Companion reference skills.** Load these for deeper context:

  • `flight-search-strategy` — full search workflow and source priority
  • `lessons-learned` — Seats.aero workflow and common failure modes (load before any award search)
  • `points-valuations` — CPP rules, opportunity cost
  • `partner-awards` — reachability through alliance + bilateral partnerships
  • `award-sweet-spots` — flag legendary redemptions
  • `booking-guidance` — booking flow + phone numbers + the "hold before transfer" rule
  • `transfer-bonuses` — live current transfer bonuses (weekly refresh) before recommending any transfer
  • `stopovers` — per-program stopover rules; can turn a one-trip plan into a multi-city itinerary at no extra mileage cost
  • `award-holds` — per-program hold rules; affects transfer timing decisions
  • `round-the-world` — when the trip request implies 3+ stops or multiple regions, RTW products may be cheaper than separate awards
  • `status-match` — when a user mentions wanting status or asks about elite tier shortcuts; covers free direct matches, paid concierge fees, and once-per-lifetime warnings

Trip Planner

"Plan a trip to Paris Aug 11-15" answered with one complete cost breakdown.

Orchestrates `compare-flights`, `compare-hotels`, `transfer-partners`, and `trip-calculator` into a unified trip analysis. Shows total trip cost in cash vs every available points strategy.

**This is an orchestration skill.** It tells the agent which skills to invoke and how to combine their outputs.

When to Use

  • "Plan a trip to Paris Aug 11-15"
  • "What's the cheapest way to do SFO to Tokyo for a week in September?"
  • "How much would a trip to Stockholm cost in points vs cash?"
  • Any request that involves both flights AND accommodation

When NOT to Use

  • Flight-only comparison (use `compare-flights`)
  • Hotel-only comparison (use `compare-hotels`)
  • Award calendar (use `award-calendar`)
  • "Should I use points?" without a specific trip (use `trip-calculator`)

Workflow

Step 1: Parse Trip Parameters

Extract from the user's request:

| Parameter | Example | Required | |-----------|---------|----------| | Origin | SFO | Yes | | Destination | Paris / CDG | Yes | | Departure date | 2026-08-11 | Yes | | Return date | 2026-08-15 | Yes (assume one-way if not given) | | Travelers | 2 adults | Default: 1 | | Cabin class | Business | Default: Economy | | Preferences | FHR hotels, nonstop flights | Optional |

If anything is ambiguous, ask. Don't guess dates or travelers.

Step 2: Run Searches in Parallel

Launch ALL searches simultaneously. Don't wait for one to finish before starting another.

PARALLEL:
  1. compare-flights: origin → destination, departure date, cabin
  2. compare-flights: destination → origin, return date, cabin (if round-trip)
  3. compare-hotels: destination, checkin = departure, checkout = return

Each of these internally runs their own parallel sub-searches (Duffel, Ignav, seats.aero, Chase, Amex, SerpAPI, Trivago, LiteAPI, Airbnb, etc).

Step 3: Combine into Trip Cost Matrix

Build a table showing total trip cost for each strategy.

**For each booking strategy, calculate total = outbound + return + hotel:**

| Strategy | Outbound | Return | Hotel (4 nights) | Total | Points Used | Cash Out of Pocket | |----------|----------|--------|-------------------|-------|-------------|-------------------| | All cash | $4,200 | $3,800 | $1,200 | **$9,200** | 0 | $9,200 | | Flights: award, Hotel: cash | $120 tax | $95 tax | $1,200 | **$1,415** | 110,000 UR | $1,415 | | Flights: award, Hotel: FHR | $120 tax | $95 tax | $8,284 (paid via points) | **$8,499** | 110,000 UR + 828,400 MR | $215 | | Flights: Chase portal, Hotel: Edit | — | — | — | **varies** | 540,000 UR | $0 | | Flights: award, Hotel: Airbnb | $120 tax | $95 tax | $780 | **$995** | 110,000 UR | $995 |

Step 4: Calculate Value Scores

For each strategy, compute:

Points value = (all-cash total - cash out of pocket) / total points used × 100

This tells you the CPP you're getting across the whole trip, not just one component.

Example:

"Flights: award + Hotel: Airbnb"
All-cash equivalent: $9,200
Cash out of pocket: $995
Points saved: $9,200 - $995 = $8,205
Points used: 110,000 UR
Trip CPP: $8,205 / 110,000 × 100 = 7.5 cpp

Step 5: Present the Trip Plan

Trip: SFO → Paris, Aug 11-15, 2 adults, Business Class

**✈️ Outbound: SFO → CDG, Aug 11**

| Option | Source | Price/Points | Currency | |--------|--------|-------------|----------| | Cash (lowest) | Duffel | $4,200 | — | | Flying Blue | seats.aero | 55,000 + $120 tax | Chase UR (1:1) | | Chase Portal Boost | chase-travel | 180,000 | Chase UR |

**✈️ Return: CDG → SFO, Aug 15**

| Option | Source | Price/Points | Currency | |--------|--------|-------------|----------| | Cash (lowest) | Duffel | $3,800 | — | | Aeroplan | seats.aero | 70,000 + $200 tax | Chase UR (1:1) |

**🏨 Hotels: Paris, Aug 11-15 (4 nights)**

| Option | Source | Per Night | Total | Points | Benefits | |--------|--------|-----------|-------|--------|----------| | SO/ Paris [EDIT] | Chase | $639 | $2,555 | 127,756 UR | Breakfast, $100 credit | | Le Bristol [FHR] | Amex | $1,849 | $8,284 | 828,400 MR | $100 credit, breakfast, upgrade | | Marriott Champs | SerpAPI | $289 | $1,156 | — | — | | Airbnb: Marais 2BR | Airbnb | $195 | $780 | — | Kitchen |

**💰 Trip Total by Strategy**

| # | Strategy | Total Cash | Points | CPP | Rating | |---|----------|-----------|--------|-----|--------| | 1 | Award flights (FB+AC) + Airbnb | $1,115 | 125,000 UR | 6.5 | ⭐ Best value | | 2 | Award flights + Chase Edit hotel | $2,870 |

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