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 map)
• Warn about seasonal schedule changes if the trip is far out (airlines typically publish schedules in waves)

5. Seat Assignment Check

• If seats are listed in the reservation, verify the seat still makes sense for the aircraft type
• Flag if an aircraft swap may have invalidated the seat assignment
• Suggest using the seatmaps skill for detailed seat recommendations if relevant

Output Format

Present results as a per-reservation audit report:

## 🌱 Gardening Report: [Trip Name]

### [Confirmation] — [Route] on [Date]

| Check | Status | Details |
|-------|--------|---------|
| Price | 🔴 DROP | Was $2,340, now $1,890 (-$450, -19%). Rebookable via United free cancel/rebook. |
| Nearby airports | 🟡 NOTE | OAK-SYD via AKL on Air NZ: $1,780 (-$560 vs SFO). Adds 2hr travel time to OAK. |
| Better cabin | 🟢 UPGRADE | First class opened up: 110K United (vs 85K booked in J). ANA F via VA would be 72.5K. |
| Routing | ✅ OK | Current routing is optimal. |
| Schedule | ✅ OK | No changes detected. |
| Seat | ⚠️ CHECK | Aircraft changed from 787-9 to 777-300ER. Seat 6A may not exist. Verify on seatmaps. |

Summary Section

After all reservations, provide a priority action list:

## 🎯 Priority Actions

1. **REBOOK NOW** — SFO-SYD dropped $450. Free cancel/rebook on United. Save $900 for 2 passengers.
2. **CONSIDER** — ANA First opened up via Virgin Atlantic for 72.5K. Currently in J at 85K United. Better product, fewer miles, but phone booking required.
3. **VERIFY** — Aircraft swap on UA870. Check seat assignment.

When to Garden

Recommend the user gardens their reservations:

• Immediately after booking — verify tickets issued, seats assigned, confirmation visible on operating airline
• Monthly for trips >30 days out
• Weekly for trips 7-30 days out
• Daily for trips <7 days out
• After any airline schedule change announcement (typically Mar/Apr and Sep/Oct)

Tools to Use

Invoke these in parallel for each reservation:

• Duffel / Ignav / Google Flights / Skiplagged / Kiwi — current cash prices
• Seats.aero — current award availability
• LiteAPI / Trivago / Skiplagged Hotels — hotel price checks
• AwardWallet — pull latest itineraries and detect changes automatically
• Seatmaps — verify seat assignments after aircraft swaps

AwardWallet Integration

AwardWallet is the best automated gardening tool available:

• It scrapes itineraries from loyalty accounts and emails
• It detects and alerts on schedule changes, aircraft swaps, seat changes, and class of service changes
• Recommend the user connect their accounts if not already done
• When running this skill, always pull fresh AwardWallet data first to catch changes the user may not know about