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Stopovers

Community
borski
stopovers

Per-program stopover rules for award redemptions. Which programs allow free stopovers, how many, how long, and which don't. Covers Icelandair, Aeroplan, Alaska, Flying Blue, Singapore, Cathay, JAL, and the negative space (BA, AA, Delta).

Overview

Publisherborski
Repositorytravel-hacking-toolkit
Skill namestopovers
Stars
690
Forks
75
Bundled files
Instructions only
LicenseMIT
Links
  • Markdown instructions

    A SKILL.md file the model loads on demand, so it only costs tokens when a request actually matches.

  • Works with any LLM

    AI skills are plain Markdown, not provider-specific code, so this works with GPT, Claude, Gemini, Grok, or a local model.

  • Self-contained

    Everything the model needs lives in the instructions — no extra files to sync.

  • Open source

    Published by borski on GitHub. Read the source before you install it.

Installation

Install the Stopovers AI skill in TypingMind to use it with any LLM, or drop it into another agent that reads SKILL.md.

1

Install in TypingMind

TypingMind installs a skill straight from its GitHub folder — it reads SKILL.md, bundles the resource files, and stores the result locally.

  1. Open the app and go to Plugins → Skills.
  2. Choose "Install from GitHub".
  3. Paste the skill folder URL below and confirm.
    https://github.com/borski/travel-hacking-toolkit/tree/main/plugins/travel-hacking-toolkit/skills/stopovers
  4. Enable the skill in any chat where you want it available.
Plugins → Skills → Add skill → From GitHub URL, then paste the folder URL and press Continue.
2

Install in another agent

Any agent that reads the Agent Skills format can use this skill — copy the folder into that agent's skills directory.

Claude Code — .claude/skills
git clone --depth 1 https://github.com/borski/travel-hacking-toolkit.git /tmp/travel-hacking-toolkit
mkdir -p .claude/skills
cp -r /tmp/travel-hacking-toolkit/plugins/travel-hacking-toolkit/skills/stopovers .claude/skills/stopovers
Restart Claude Code after copying so it picks up the new skill.

Use it in TypingMind

Enable Stopovers in any TypingMind chat and the model takes it from there. Its name and description sit in the system prompt, and the moment a request matches, the model loads the full instructions itself — you never invoke it by hand, and it costs no tokens until it is actually used.

The model loads Stopovers on its own as soon as a request matches it.

Works with any AI model

AI skills are plain Markdown instructions rather than provider-specific code, so Stopovers is not tied to the model it was written for. Install it once in TypingMind and use it with GPT-5, Claude, Gemini, Grok, DeepSeek, Mistral, Llama, or a local model you run yourself — all on your own API keys.

  • Loaded only when it is needed

    The system prompt carries just the name and description. The instructions are fetched on the first matching request, so an idle skill costs nothing.

  • Switch models mid-chat

    Because the skill is instructions rather than code, changing model does not break it — the next model reads the same SKILL.md.

Skill instructions

This is the SKILL.md content the model loads. Read it before installing — a skill is instructions your model will follow.

Stopover Rules per Loyalty Program

Reference data for which programs allow stopovers on award redemptions, how many, where, for how long, and at what cost. Sourced primarily from each airline's own award rules pages, cross-checked against Frequent Miler, OMAAT, Travel Miles 101, Prince of Travel, and Upgraded Points.

Data lives in data/stopovers.json. Refresh cadence is 90 days because stopover rules change rarely (much less often than transfer bonuses or program valuations).

What Is a Stopover?

A planned interruption of a journey at a point between origin and destination. The IATA standard definition is:

  • More than 24 hours for international itineraries
  • More than 4 hours for domestic itineraries (US/Canada)

Each loyalty program defines its own rules within or beyond this baseline. Some programs let you stop for a week. Some let you stop for 365 days. Some don't allow stopovers at all.

The headline value: a free stopover lets you visit two destinations on a single award. Iceland on the way to Europe. Tokyo on the way to Bangkok. Singapore on the way to Sydney.

When to Use This Skill

  • User wants to plan a multi-city trip and asks "what's the best program for stopovers?"
  • User asks about a specific program's stopover rule (e.g. "does Aeroplan allow stopovers?")
  • Building a trip itinerary that could benefit from a free second destination
  • Comparing programs for award redemption when stopover flexibility matters
  • Identifying the cheapest "free vacation in Iceland" via Icelandair stopover
  • Researching JetBlue + Icelandair partner award routings

When NOT to Use

  • Cash flight stopovers (most cash fares have layover rules but not "free stopover" perks; check the airline's fare conditions instead)
  • Booking the actual itinerary (use the program's website or call the booking phone)
  • Award holds (use award-holds skill — that's a different concept)
  • Round-the-world tickets (use round-the-world skill — different framework with global routing rules)

Quick Reference Table

The full data is in data/stopovers.json. Headlines:

Programs That Allow Stopovers (positive)

ProgramMax Round-TripMax DaysCostBookingConfidence
Aeroplan2 (1 per direction)455,000 ptsOnlineVERIFIED
Alaska Atmos Rewards2 (1 per one-way)unspecifiedFreePhoneVERIFIED
ANA Mileage Club1unspecifiedFreeOnlineLIKELY
Avianca LifeMiles1unspecifiedFreeOnlineLIKELY
Cathay Asia Miles2unspecifiedFreeOnlineVERIFIED
Copa ConnectMiles1unspecifiedFreeOnlineLIKELY
Etihad Guest1unspecifiedFreePhoneLIKELY
Flying Blue (AF/KLM)unlimitedup to 365FreePhoneVERIFIED
Icelandair Saga Club2 (transatlantic)7FreeOnlineVERIFIED
JAL Mileage Bank3 (partner only)unspecifiedFreePhoneVERIFIED
Korean SKYPASS1unspecifiedFreePhoneLIKELY
Lufthansa Miles & More2unspecifiedFreeOnlineLIKELY
Qatar Privilege Club1unspecifiedFreePhoneUNVERIFIED
Singapore KrisFlyer1 (Saver) / 2 (Advantage)30FreeOnlineVERIFIED
TAP Miles & Go1 (partners only)unspecifiedFreeOnlineLIKELY
Turkish Miles & Smiles1unspecifiedFreePhoneLIKELY
United (Excursionist Perk)DISCONTINUED Aug 2025———VERIFIED

Programs That Do NOT Allow Stopovers (negative space)

These programs price each segment as its own award. Long layovers up to ~24 hours are still typically permitted but offer no perk.

  • British Airways Avios — each segment priced separately
  • American Airlines AAdvantage — long layovers up to 24h only
  • Delta SkyMiles — long layovers up to 24h only
  • Iberia Plus Avios — same as BA
  • Virgin Atlantic Flying Club — no formal stopover program
  • JetBlue TrueBlue — revenue-based, segment-priced

For full details, restrictions, recent changes, and primary sources for any program, query data/stopovers.json.

The Iceland Callout

Icelandair's stopover program is the single best free-vacation perk built into a flight ticket in commercial aviation. Some specifics worth highlighting:

  • Free at no additional airfare on every transatlantic Icelandair itinerary
  • Up to 7 nights in Reykjavík (some Saga Premium fares allow longer)
  • Same rules apply on cash bookings AND on award redemptions through Saga Club
  • 70+ year history — Icelandair has been doing this since their founding
  • Bookable via JetBlue TrueBlue partner award (added 2024) — so transferable points programs like Bilt, Chase UR transfers etc. can reach this
  • No tricks — book a transatlantic Icelandair flight, choose your stopover length when booking, done

When recommending stopover-friendly programs to a US-Europe traveler with flexible plans, this should usually be near the top of the list.

Primary source: icelandair.com/flights/stopover

Reading the Data File

bash
# All programs that allow stopovers, sorted by max round-trip stopovers
jq '.programs[] | select(.category == "positive") |
    {name, max_rt: .max_stopovers_round_trip, surcharge: .surcharge_points, booking: .booking_method}' \
    data/stopovers.json | head -40

# Find programs that allow free phone-bookable stopovers
jq '.programs[] | select(.category == "positive" and .surcharge_points == 0 and .booking_method == "phone") |
    {name, max_rt: .max_stopovers_round_trip, restrictions: .restrictions}' \
    data/stopovers.json

# Programs that do NOT allow stopovers (negative space)
jq '.programs[] | select(.category == "negative") | {name, restrictions}' data/stopovers.json

# All sources/citations for a given program
jq '.programs[] | select(.id == "aeroplan") | .sources' data/stopovers.json

# Recently changed programs (last 24 months)
jq '.programs[] | select(.recent_changes != null) | {name, recent_changes}' data/stopovers.json

# Discontinued programs (e.g. United Excursionist)
jq '.programs[] | select(.discontinued == true) | {name, discontinued_date, restrictions}' data/stopovers.json

Decision Rules

When a user is planning a trip and stopovers are relevant, follow these:

  1. Free Iceland stopover is the easiest second country for any US-Europe traveler. It's built into the cash fare AND the award redemption. Mention it whenever the trip includes US/Canada to/from Europe.

  2. Map hub airports to programs. Match the user's likely connecting hub to a program with stopover rights:

    • Tokyo (NRT/HND) → ANA, JAL, Singapore (transit), Korean partner
    • Hong Kong (HKG) → Cathay
    • Singapore (SIN) → Singapore KrisFlyer
    • Doha (DOH) → Qatar
    • Abu Dhabi (AUH) → Etihad
    • Istanbul (IST) → Turkish
    • Amsterdam (AMS) / Paris (CDG) → Flying Blue
    • Reykjavik (KEF) → Icelandair
    • Seoul (ICN) → Korean
    • Bogotá (BOG) → Avianca
    • Panama City (PTY) → Copa
    • Frankfurt (FRA) / Munich (MUC) → Lufthansa
  3. Alaska Atmos is the most generous Western program for partner stopovers but requires phone booking. Allow 30+ minutes per call.

  4. Flying Blue allows unlimited stopovers but requires phone booking. Some agents incorrectly say only AMS/CDG hub stopovers — cite the FAQ at flyingblue.us/en/spend/flights/rewards if pushed back on.

  5. Singapore KrisFlyer Saver awards beat Advantage on cost but allow only 1 stopover round-trip vs 2.

  6. Turkish Miles & Smiles is famously hard to book by phone but offers excellent Star Alliance pricing if you're patient.

  7. United Excursionist Perk is GONE as of August 21, 2025. Don't recommend MileagePlus for stopover routing anymore.

  8. For BA Avios, AA AAdvantage, Delta SkyMiles — these don't allow stopovers. Either book each segment as its own award (for the redemption price) or use a different program (e.g. Alaska Atmos for Cathay, Flying Blue for Delta metal).

  9. When in doubt, the program's own award rules page is canonical. Frequent Miler, OMAAT, and Travel Miles 101 are cross-checks.

Cross-References

  • partner-awards — what you can book through a program (alliance + bilateral) before checking stopover rules
  • alliances — alliance membership for the multi-carrier oneworld/Star/SkyTeam stopover rules
  • booking-guidance — phone numbers for programs that require phone booking (Flying Blue, Alaska, Turkish, Etihad, Qatar)
  • transfer-partners — transferable point currency that reaches the program for the stopover redemption
  • transfer-bonuses — current transfer promotions that may make a stopover-friendly program even cheaper
  • award-holds — most stopover-friendly programs (Aeroplan, Flying Blue, Alaska) DO NOT allow holds, so you can't lock the multi-city award before transferring. Plan timing carefully.
  • round-the-world — RTW products are the natural next step when a single stopover isn't enough. Star Alliance RTW (a paid cash fare via staralliance.com, NOT a mileage award) allows up to 15 stopovers in one ticket. The only miles-priced RTW survivor is Lufthansa Miles & More.

Source Hierarchy (Per Research Integrity Protocol)

  1. The airline's own award rules page — canonical when available
  2. Frequent Miler — most respected secondary source for current accuracy
  3. OMAAT (One Mile at a Time) — comprehensive guides, occasionally outdated
  4. Travel Miles 101 — accurate baseline reference
  5. Prince of Travel — strong on Aeroplan and Alaska
  6. Upgraded Points / TPG / View From The Wing — useful but often slower to update on devaluations

When sources disagree, the airline's own page wins. When the airline's page is silent or ambiguous, the most-recent Frequent Miler post wins. Never make up rules.

Avoiding Fabrication

  • The data file has confidence markers (VERIFIED / LIKELY / UNVERIFIED). When confidence is below VERIFIED, communicate that uncertainty to the user.
  • If a user asks about a program not in the data file, say so honestly. Don't guess. Look it up via Frequent Miler or the airline's own page first.
  • Stopover rules can quietly change. Note the last_verified date when you cite a rule. Anything older than 90 days should be re-verified before being recommended for an actual booking.

Frequently asked questions

What does the Stopovers AI skill do?

Per-program stopover rules for award redemptions. Which programs allow free stopovers, how many, how long, and which don't. Covers Icelandair, Aeroplan, Alaska, Flying Blue, Singapore, Cathay, JAL, and the negative space (BA, AA, Delta).

Why use Stopovers on TypingMind?

Because you install it once and use it with any model. Stopovers is plain Markdown rather than provider-specific code, so the same skill runs on GPT-5, Claude, Gemini, Grok, or a local model — and you can switch model mid-chat without it breaking. TypingMind runs on your own API keys, so you pay providers directly instead of a per-seat subscription, and your skills and chats stay in your own storage.

How do I install Stopovers in TypingMind?

Open Plugins → Skills → Install from GitHub in TypingMind and paste https://github.com/borski/travel-hacking-toolkit/tree/main/plugins/travel-hacking-toolkit/skills/stopovers. TypingMind reads its SKILL.md and installs it as a skill you can enable per chat.

Which AI models can use Stopovers?

Any model you connect in TypingMind. AI skills are plain Markdown instructions rather than provider-specific code, so GPT, Claude, Gemini, Grok, and local models can all load this skill when a request matches it.

How many AI models can I use with Stopovers?

As many as you like. As long as a model supports skills, you can use Stopovers with it — GPT, Claude, Gemini, Grok, DeepSeek, Mistral, Llama and more — all on TypingMind with your own API keys.

Is the Stopovers AI skill free?

Yes. It is published on GitHub by borski under the MIT license. You only pay your own AI provider for the tokens you use.

What are AI skills?

An AI skill is a reusable instruction bundle that teaches an AI model how to do one specific task. It follows the open Agent Skills format: a SKILL.md file with a name and description, plus any scripts, templates or reference files the model may need. The model reads the instructions only when your request matches the skill, so an installed skill costs nothing until it is used.

How are AI skills different from plugins or MCP servers?

A plugin or MCP server gives a model new tools to call — code that runs somewhere and returns a result. An AI skill gives the model knowledge and process instead: how to approach a task, which steps to follow, what good output looks like. Skills are plain Markdown, so they need no server, no API key and no runtime, and they work with any model.

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