/gardening

name: gardening
description: Audit and tend to existing travel reservations. Reads a user-provided reservations file, then systematically checks every booking for price drops, better cabin availability, improved routings, schedule changes, nearby airport alternatives, and award repricing opportunities. Invoke proactively on a regular cadence or when the user says "garden", "check my bookings", "audit reservations", "price drop", "better routing", "did my flight change", "tend reservations", "reservation maintenance", or "check my trips".
category: orchestration
summary: Audit existing reservations for price drops, better cabins, schedule changes, and improved routings.
api_key: Uses individual skill keys

Reservation Gardening

**Concept:** "Gardening" (coined by Nicholas Kralev, popularized by View from the Wing) means regularly tending to your travel reservations — catching problems early and spotting opportunities to upgrade, rebook, or save money.

Reservations File

The user points this skill at a file containing their current bookings. The file path is provided when invoking the skill (e.g., `~/trips/reservations.json` or `~/trips/reservations.yaml`).

**If no file path is provided, ask the user for it.**

Expected File Format

The file should contain an array of reservations. Each reservation should include as much of the following as possible:

[
  {
    "trip_name": "Sydney Vacation",
    "confirmation": "ABC123",
    "type": "flight",
    "booking_date": "2026-03-15",
    "program": "United MileagePlus",
    "paid_with": "points",
    "cost": { "miles": 85000, "taxes_usd": 45.60 },
    "cash_price_at_booking": 2340,
    "segments": [
      {
        "airline": "UA",
        "flight": "UA870",
        "origin": "SFO",
        "destination": "SYD",
        "date": "2026-09-12",
        "departure": "22:30",
        "arrival": "07:15+2",
        "cabin": "business",
        "fare_class": "I",
        "seat": "6A",
        "aircraft": "787-9"
      }
    ],
    "passengers": 2,
    "notes": "Booked with Chase UR transfer"
  },
  {
    "trip_name": "Sydney Vacation",
    "confirmation": "HTL-9876",
    "type": "hotel",
    "hotel_name": "Park Hyatt Sydney",
    "program": "World of Hyatt",
    "paid_with": "points",
    "cost": { "points": 30000, "per_night": true },
    "cash_price_at_booking": 850,
    "checkin": "2026-09-14",
    "checkout": "2026-09-18",
    "room_type": "King Deluxe",
    "guests": 2
  }
]

Flexible on format — YAML, JSON, CSV, or even markdown tables are fine. Parse whatever is provided.

Gardening Checklist

For **every reservation** in the file, run through this checklist. Parallelize searches across reservations for speed.

1. Price Drop Detection (PRIORITY)

This is the user's #1 interest. For each booking:

**Cash bookings:**

• Search current cash prices on the SAME flights/dates using Duffel, Ignav, Google Flights, Skiplagged, and Kiwi
• Search **nearby airports** (within ~100 miles / reasonable driving distance) for the same dates
• SFO → also check OAK, SJC
• LAX → also check BUR, SNA, LGB, ONT
• NYC → also check JFK, EWR, LGA
• CHI → also check ORD, MDW
• DCA → also check IAD, BWI
• Use common sense for other cities
• Compare current price vs booked price
• Flag if current price is **≥10% lower** or **≥$50 cheaper** (whichever triggers first)
• Note the airline's rebooking/price-match policy (e.g., Southwest auto-refunds the difference; most US airlines allow free cancellation within 24hrs of booking; some credit cards have price protection)

**Award bookings:**

• Search current award availability on the same route/dates via Seats.aero and the booking program
• Check if the same flight is now available for **fewer miles**
• Check if a **better cabin** is now available at the same or similar mileage price
• Check if a **different program** now offers the same flight cheaper (cross-reference `data/sweet-spots.json`)
• For dynamic-pricing programs (United, Delta, Aeroplan on some partners), prices fluctuate — a drop is rebookable

**Hotels:**

• Search current rates on the same hotel via LiteAPI, Trivago, Skiplagged Hotels
• Check portal pricing (Chase UR, Amex) if the user has those currencies
• For award hotel stays, check if the points price dropped
• Flag cash rate drops and compare against the award value (cpp math)

2. Better Routing / Connection Check

For each flight:

• Search the same origin-destination pair on the same date for:
• **Nonstop options** that may have opened up (if the booking has stops)
• **Shorter connections** (if booked connection is >3 hours)
• **Better connection airports** (avoiding known bad ones like ORD in winter, LHR T5-to-T3 transfers)
• Search **nearby origin/destination airports** for:
• Better nonstop availability
• Significantly cheaper fares
• Better timing (red-eye vs daytime)
• Flag routes where the total travel time can be reduced by **≥1 hour**

3. Better Cabin Availability

For each flight booked in economy or premium economy:

• Check if **business or first class award space** has opened up on the same flight
• Check the price in the user's booking program AND alternative programs
• Calculate the **incremental cost** to upgrade (e.g., "upgrade from 38K economy to 85K business = 47K more miles, worth 3.2cpp against $1,500 cash fare difference")
• For paid tickets, check if paid upgrades, upgrade certificates, or mileage upgrades are available

For each flight already in business:

• Check if **first class** has opened up (especially on airlines with great F products: ANA, Singapore, Cathay, Emirates)

4. Schedule Change Detection

• If the user provides confirmation codes / PNRs, note that AwardWallet can monitor these automatically
• Flag any segments where the **departure time may have shifted** (search current schedules)
• Check for **aircraft type changes** (e.g., 787-9 → 737 is a significant downgrade; 777-300ER → A350 may change seat ma