Gardening

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)