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Agent skill

Stopovers

by borski in borski/travel-hacking-toolkit

Per-program stopover rules for award redemptions. An agent skill from borski/travel-hacking-toolkit.

MITAuto-check passed

Install Stopovers

skills CLI
$ npx skills add borski/travel-hacking-toolkit --skill stopovers -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install borski/travel-hacking-toolkit stopovers --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/borski/travel-hacking-toolkit.git skills-src && mkdir -p .claude/skills && cp -r skills-src/plugins/travel-hacking-toolkit/skills/stopovers .claude/skills/stopovers && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
stopovers
GitHub stars
688
Token cost
~2.8k tokens
SKILL.md length
1,273 words
Files
1
Skills in repo
46
Repo updated
First seen
Licence
MIT

At a glance

Per-program stopover rules for award redemptions. An agent skill from borski/travel-hacking-toolkit.

  • Works in 9 steps: Free Iceland stopover is the easiest… → Map hub airports to programs. Match the… → Alaska Atmos is the most generous… → …
  • SKILL.md covers What Is a Stopover?, When to Use This Skill, When NOT to Use and Quick Reference Table, plus 6 more sections
  • Calls jq

What it does

Stopovers is an agent skill from borski/travel-hacking-toolkit. 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).

Its SKILL.md is about 2.8k tokens, which your agent loads only when the skill is triggered. It is a single SKILL.md file with no bundled scripts.

The repository describes itself as: AI-powered travel hacking and search with cash, points, miles, and award flights. Drop-in skills and MCP servers for Claude, Codex, and OpenCode. The licence is MIT.

Example prompts

  • “/stopovers”

Requirements

  • Pre-approved tools (allowed-tools): Bash(jq *), Read

Workflow steps

9 steps, taken from the first numbered list in SKILL.md.

  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…
  2. Map hub airports to programs. Match the user's likely connecting hub to a program with stopover rights
  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…
  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…
  9. When in doubt, the program's own award rules page is canonical. Frequent Miler, OMAAT, and Travel Miles 101 are cross-checks.

What it can do on your machine

Read from SKILL.md and the folder at commit db82131. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves these tools, so the agent can use them without asking each time:

    • Bash(jq *)
    • Read

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    Shell commands in SKILL.md call:

    • jq

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    Links to these hosts (documentation or services it may open):

    • icelandair.com
    • flyingblue.us

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Stopovers loads about 2.8k tokens when it runs. Until then it costs about 62 tokens; SKILL.md has 1,273 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~62
When it runs · the whole SKILL.md, loaded when a task matches
~2.8k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from borski/travel-hacking-toolkit at commit db82131, republished under its MIT licence (© borski). 1,273 words, ~2,820 tokens.

Download SKILL.mdSave it as .claude/skills/stopovers/SKILL.md (or your agent's skills folder).
name
stopovers
description
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).
allowed-tools
Bash(jq *), Read
category
reference
summary
Per-program stopover rules for award redemptions. Includes Icelandair free stopover, Aeroplan, Alaska Atmos, Flying Blue, Singapore tiers, plus the negative…

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
Show full SKILL.md (584 more words)Show less

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.

© borski, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

Just SKILL.md in plugins/travel-hacking-toolkit/skills/stopovers of borski/travel-hacking-toolkit.

Open the folder on GitHubat commit db82131

Compare with similar skills

Stopovers next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.

Stopovers compared with similar skills
SkillStarsUsed inTokensAuto-checkLicenceRepo updated
Stopovers this skillborski/travel-hacking-toolkit688—~2.8kAutomated safety check: PassMIT
Strict Programming Practicescode-yeongyu/oh-my-openagent70k—~9.5kAutomated safety check: PassCustom licence
Referral Programalirezarezvani/claude-skills28k—~3.4kAutomated safety check: PassMIT
Intern Programsickn33/agentic-awesome-skills47k1 repos~3.9kAutomated safety check: PassMIT
Mentorship Programsickn33/agentic-awesome-skills47k1 repos~3.7kAutomated safety check: PassMIT
Implementing Anti Phishing Training Programmukul975/Anthropic-Cybersecurity-Skills34k—~1.3kAutomated safety check: PassApache-2.0

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Questions about Stopovers

What does Stopovers do?

Per-program stopover rules for award redemptions. An agent skill from borski/travel-hacking-toolkit. Stopovers is an agent skill from borski/travel-hacking-toolkit. Per-program stopover rules for award redemptions.

How do I install Stopovers in Claude Code?

Run `npx skills add borski/travel-hacking-toolkit --skill stopovers -a claude-code`. Or copy the skill folder (plugins/travel-hacking-toolkit/skills/stopovers in borski/travel-hacking-toolkit) into .claude/skills/stopovers in your project. Claude Code loads it when a task matches its description.

How do I install Stopovers in Codex?

Run `npx skills add borski/travel-hacking-toolkit --skill stopovers -a codex`. Or copy the skill folder (plugins/travel-hacking-toolkit/skills/stopovers in borski/travel-hacking-toolkit) into .agents/skills/stopovers in your project. Codex loads it when a task matches its description.

Can I use Stopovers in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add borski/travel-hacking-toolkit --skill stopovers -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/stopovers, .gemini/skills/stopovers, .github/skills/stopovers and .opencode/skills/stopovers in your project.

What does Stopovers need to run?

Going by SKILL.md and its folder, Stopovers needs the command-line tools its instructions call (jq). Its frontmatter pre-approves these tools: Bash(jq *), Read.

Does Stopovers access the network?

SKILL.md names 2 domains. As links in the text: icelandair.com and flyingblue.us. This is read from the text; nothing was executed.

Is Stopovers safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.

What licence does Stopovers use?

Stopovers is published under the MIT licence (the repository's licence). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does Stopovers use?

About 2.8k tokens (SKILL.md is roughly 11k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full.

What are the alternatives to Stopovers?

Skills that share tags, products or a category with Stopovers: Strict Programming Practices (code-yeongyu/oh-my-openagent, 70k stars), Referral Program (alirezarezvani/claude-skills, 28k stars), Intern Program (sickn33/agentic-awesome-skills, 47k stars) and Mentorship Program (sickn33/agentic-awesome-skills, 47k stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains Stopovers?

borski (a GitHub user) maintains it in borski/travel-hacking-toolkit, which has 688 GitHub stars. The repository holds 46 skills in this directory. The repository was last updated on October 5, 2026.

Source: borski/travel-hacking-toolkit on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.