diff --git a/agenda/build_place_yaml.py b/agenda/build_place_yaml.py
new file mode 100644
index 0000000..bc346f4
--- /dev/null
+++ b/agenda/build_place_yaml.py
@@ -0,0 +1,257 @@
+"""Build airport and station YAML entries from Wikidata."""
+
+import argparse
+import typing
+from pathlib import Path
+
+import requests
+import yaml
+
+API_URL = "https://www.wikidata.org/w/api.php"
+PERSONAL_DATA_DIR = Path("~/src/personal-data").expanduser()
+USER_AGENT = "agenda-build-place-yaml/0.1"
+
+Entity = dict[str, typing.Any]
+Entities = dict[str, Entity]
+
+
+class WikidataClient:
+    """Small Wikidata API client for place lookups."""
+
+    def __init__(self) -> None:
+        """Create a Wikidata API session."""
+        self.session = requests.Session()
+        self.session.headers.update({"User-Agent": USER_AGENT})
+
+    def get_json(self, params: dict[str, str]) -> dict[str, typing.Any]:
+        """Fetch JSON from Wikidata."""
+        response = self.session.get(API_URL, params=params)
+        response.raise_for_status()
+        return typing.cast(dict[str, typing.Any], response.json())
+
+    def get_alpha2_country_code(self, qid: str) -> str:
+        """Query the Wikidata API for alpha-2 country code."""
+        data = self.get_json(
+            {
+                "action": "wbgetclaims",
+                "entity": qid,
+                "property": "P297",
+                "format": "json",
+            }
+        )
+        p297 = data["claims"]["P297"]
+        return typing.cast(str, p297[0]["mainsnak"]["datavalue"]["value"]).lower()
+
+    def search_entities(self, query: str) -> Entities:
+        """Search Wikidata and return detailed entities."""
+        search_data = self.get_json(
+            {
+                "action": "query",
+                "list": "search",
+                "format": "json",
+                "srsearch": query,
+            }
+        )
+        search_results = search_data["query"]["search"]
+        if not search_results:
+            return {}
+
+        ids = [result["title"] for result in search_results]
+        entity_data = self.get_json(
+            {
+                "action": "wbgetentities",
+                "format": "json",
+                "ids": "|".join(ids),
+            }
+        )
+        return typing.cast(Entities, entity_data["entities"])
+
+
+def entity_names(entity: Entity) -> set[str]:
+    """Return labels and aliases for a Wikidata entity."""
+    names: set[str] = {lang["value"] for lang in entity.get("labels", {}).values()}
+    for alias_list in entity.get("aliases", {}).values():
+        for alias in alias_list:
+            names.add(alias["value"])
+    return names
+
+
+def exact_station_match(station_name: str, entity: Entity) -> bool:
+    """Return whether the entity names match the requested station name."""
+    names = entity_names(entity)
+    return station_name in names or f"{station_name} station" in names
+
+
+def entity_claim_value(
+    entity: Entity, property_id: str, default: typing.Any = None
+) -> typing.Any:
+    """Return the first Wikidata claim value for a property."""
+    claims = entity.get("claims", {})
+    if property_id not in claims:
+        return default
+    return claims[property_id][0]["mainsnak"]["datavalue"]["value"]
+
+
+def build_station_info(
+    client: WikidataClient, station_name: str, entity_id: str, entity: Entity
+) -> dict[str, typing.Any]:
+    """Build a stations.yaml entry."""
+    coords = entity_claim_value(entity, "P625")
+    country_value = entity_claim_value(entity, "P17")
+    uic = entity_claim_value(entity, "P722")
+    uk_station_code = entity_claim_value(entity, "P4755")
+
+    station_info: dict[str, typing.Any] = {
+        "name": station_name,
+        "latitude": coords["latitude"],
+        "longitude": coords["longitude"],
+        "country": client.get_alpha2_country_code(country_value["id"]),
+        "wikidata": entity_id,
+        "routes": {},
+    }
+
+    if uic is not None:
+        station_info["uic"] = uic
+    if uk_station_code is not None:
+        station_info["alpha3"] = uk_station_code
+
+    return station_info
+
+
+def search_for_station(
+    client: WikidataClient, station_name: str
+) -> dict[str, typing.Any]:
+    """Search for a station and return a stations.yaml entry."""
+    haswbstatement = "P31=Q55488|P31=Q18543139|P31=Q1147171"
+    entities = client.search_entities(f"{station_name} haswbstatement:{haswbstatement}")
+
+    for entity_id, entity in entities.items():
+        if exact_station_match(station_name, entity):
+            return build_station_info(client, station_name, entity_id, entity)
+
+    if entities:
+        entity_id, entity = next(iter(entities.items()))
+        return build_station_info(client, station_name, entity_id, entity)
+
+    raise ValueError(f"No Wikidata station found for {station_name!r}")
+
+
+def build_airport_info(
+    client: WikidataClient, iata: str, entity_id: str, entity: Entity
+) -> dict[str, typing.Any]:
+    """Build an airports.yaml entry."""
+    label = entity["labels"]["en"]["value"]
+    claims = entity["claims"]
+    coords = claims["P625"][0]["mainsnak"]["datavalue"]["value"]
+    country_qid = claims["P17"][0]["mainsnak"]["datavalue"]["value"]["id"]
+
+    info: dict[str, typing.Any] = {
+        "iata": iata,
+        "name": label,
+        "city": label,
+        "country": client.get_alpha2_country_code(country_qid),
+        "latitude": coords["latitude"],
+        "longitude": coords["longitude"],
+        "qid": entity_id,
+    }
+
+    website = entity_claim_value(entity, "P856")
+    if website is not None:
+        info["website"] = website
+
+    return info
+
+
+def search_for_airport(client: WikidataClient, iata: str) -> dict[str, typing.Any]:
+    """Search for an airport by IATA code and return an airports.yaml entry."""
+    entities = client.search_entities(f"haswbstatement:P238={iata.upper()}")
+    if not entities:
+        raise ValueError(f"No Wikidata airport found for IATA code {iata!r}")
+
+    entity_id, entity = next(iter(entities.items()))
+    return build_airport_info(client, iata.upper(), entity_id, entity)
+
+
+def load_yaml(path: Path) -> typing.Any:
+    """Load a YAML file."""
+    return yaml.safe_load(path.read_text())
+
+
+def dump_yaml(data: typing.Any) -> str:
+    """Dump YAML using the local personal-data style."""
+    return yaml.dump(data, sort_keys=False, allow_unicode=True)
+
+
+def dump_yaml_list_with_blank_lines(items: list[dict[str, typing.Any]]) -> str:
+    """Dump a YAML list with a blank line between top-level items."""
+    text = dump_yaml(items).lstrip()
+    return text.replace("\n- ", "\n\n- ")
+
+
+def upsert_station(data_dir: Path, station_info: dict[str, typing.Any]) -> bool:
+    """Add or replace a station entry. Return True when an existing entry changed."""
+    path = data_dir / "stations.yaml"
+    stations = typing.cast(list[dict[str, typing.Any]], load_yaml(path))
+
+    for index, station in enumerate(stations):
+        if station.get("name") == station_info["name"]:
+            stations[index] = station_info
+            path.write_text(dump_yaml_list_with_blank_lines(stations))
+            return True
+
+    stations.append(station_info)
+    path.write_text(dump_yaml_list_with_blank_lines(stations))
+    return False
+
+
+def upsert_airport(data_dir: Path, airport_info: dict[str, typing.Any]) -> bool:
+    """Add or replace an airport entry. Return True when an existing entry changed."""
+    path = data_dir / "airports.yaml"
+    airports = typing.cast(dict[str, dict[str, typing.Any]], load_yaml(path))
+    iata = typing.cast(str, airport_info["iata"])
+    existed = iata in airports
+    airports[iata] = airport_info
+    path.write_text(dump_yaml(airports))
+    return existed
+
+
+def station_main(argv: list[str] | None = None) -> int:
+    """CLI entrypoint for building and importing a station YAML entry."""
+    parser = argparse.ArgumentParser(
+        description="Add or update a station in personal-data/stations.yaml."
+    )
+    parser.add_argument("station_name")
+    parser.add_argument("--data-dir", default=str(PERSONAL_DATA_DIR))
+    parser.add_argument("--print-only", action="store_true")
+    args = parser.parse_args(argv)
+
+    station_info = search_for_station(WikidataClient(), args.station_name)
+    if args.print_only:
+        print(dump_yaml_list_with_blank_lines([station_info]).strip())
+        return 0
+
+    replaced = upsert_station(Path(args.data_dir), station_info)
+    action = "Updated" if replaced else "Added"
+    print(f"{action} station {station_info['name']} in {args.data_dir}/stations.yaml")
+    return 0
+
+
+def airport_main(argv: list[str] | None = None) -> int:
+    """CLI entrypoint for building and importing an airport YAML entry."""
+    parser = argparse.ArgumentParser(
+        description="Add or update an airport in personal-data/airports.yaml."
+    )
+    parser.add_argument("iata")
+    parser.add_argument("--data-dir", default=str(PERSONAL_DATA_DIR))
+    parser.add_argument("--print-only", action="store_true")
+    args = parser.parse_args(argv)
+
+    airport_info = search_for_airport(WikidataClient(), args.iata)
+    if args.print_only:
+        print(dump_yaml({airport_info["iata"]: airport_info}).strip())
+        return 0
+
+    replaced = upsert_airport(Path(args.data_dir), airport_info)
+    action = "Updated" if replaced else "Added"
+    print(f"{action} airport {airport_info['iata']} in {args.data_dir}/airports.yaml")
+    return 0
diff --git a/agenda/generate_booking_yaml.py b/agenda/generate_booking_yaml.py
new file mode 100644
index 0000000..f9743c1
--- /dev/null
+++ b/agenda/generate_booking_yaml.py
@@ -0,0 +1,457 @@
+"""Generate travel booking YAML from booking text or a booking URL."""
+
+import argparse
+import configparser
+import importlib
+import json
+import os
+import sys
+import typing
+from dataclasses import dataclass
+from datetime import date, datetime
+from pathlib import Path
+
+import html2text
+import lxml.html
+import openai
+import requests
+import yaml
+
+USER_AGENT = "generate-booking-yaml/0.1"
+REPO_ROOT = Path(__file__).resolve().parent.parent
+SPEC_PATH = REPO_ROOT / "docs" / "personal-data-yaml.md"
+PERSONAL_DATA_DIR = Path("~/src/personal-data").expanduser()
+
+
+class TripLike(typing.Protocol):
+    """Trip attributes needed for booking import matching."""
+
+    start: date
+    end: date | None
+
+
+@dataclass(frozen=True)
+class BookingConfig:
+    """Configuration for one travel booking YAML generator."""
+
+    booking_type: str
+    yaml_filename: str
+    spec_heading: str
+    json_key: str = "booking"
+
+
+BOOKING_CONFIGS: dict[str, BookingConfig] = {
+    "flight": BookingConfig(
+        booking_type="flight",
+        yaml_filename="flights.yaml",
+        spec_heading="flights.yaml",
+    ),
+    "train": BookingConfig(
+        booking_type="train",
+        yaml_filename="trains.yaml",
+        spec_heading="trains.yaml",
+    ),
+}
+
+
+def read_api_key() -> str:
+    """Read API key from ~/.config/openai/config."""
+    config_path = os.path.expanduser("~/.config/openai/config")
+    parser = configparser.ConfigParser()
+    parser.read(config_path)
+    return parser["openai"]["api_key"]
+
+
+def read_markdown_section(markdown_text: str, heading: str) -> str:
+    """Return one second-level markdown section by heading text."""
+    section_headings = (f"## `{heading}`", f"## {heading}")
+    start = -1
+    matched_heading = ""
+    for section_heading in section_headings:
+        start = markdown_text.find(section_heading)
+        if start != -1:
+            matched_heading = section_heading
+            break
+    if start == -1:
+        raise ValueError(f"Could not find section for heading {heading!r}")
+
+    next_heading = markdown_text.find("\n## ", start + len(matched_heading))
+    if next_heading == -1:
+        return markdown_text[start:].strip()
+    return markdown_text[start:next_heading].strip()
+
+
+def yaml_format_description(config: BookingConfig) -> str:
+    """Return relevant personal-data YAML documentation for the prompt."""
+    spec_text = SPEC_PATH.read_text()
+    sections = [
+        read_markdown_section(spec_text, "General Rules"),
+        read_markdown_section(spec_text, "Cross-File References"),
+        read_markdown_section(spec_text, config.spec_heading),
+    ]
+    return "\n\n".join(sections)
+
+
+def read_existing_bookings(
+    config: BookingConfig, data_dir: Path = PERSONAL_DATA_DIR
+) -> str:
+    """Read the existing YAML file for examples and local style."""
+    path = data_dir / config.yaml_filename
+    return path.read_text()
+
+
+def build_prompt(
+    booking_text: str,
+    config: BookingConfig,
+    current_bookings: str | None = None,
+) -> str:
+    """Build prompt to pass to the LLM."""
+    bookings = current_bookings
+    if bookings is None:
+        bookings = read_existing_bookings(config)
+
+    return f"""
+I keep a record of all my {config.booking_type} bookings in a YAML file.
+
+Use this YAML format specification:
+
+{yaml_format_description(config)}
+
+Here's my current list of bookings for examples of local style and known
+references.
+===
+{bookings}
+===
+Here's a new booking I just made.
+
+Return the YAML representation for this booking using the documented format and
+the same local style as my existing bookings.
+
+Rules:
+- Wrap the response in a JSON object with a single key "{config.json_key}" that
+  contains the booking in YAML.
+- The value of "{config.json_key}" must be YAML text, not JSON.
+- Exclude the top-level "trip" key from the YAML.
+- Do not invent details that are not present in the booking text.
+- Quote prices and identifiers that might otherwise be parsed as numbers.
+
+===
+{booking_text}
+"""
+
+
+def get_from_open_ai(prompt: str, model: str = "gpt-5.4") -> dict[str, str]:
+    """Pass prompt to OpenAI and get reply."""
+    client = openai.OpenAI(api_key=read_api_key())
+
+    response = client.chat.completions.create(
+        messages=[{"role": "user", "content": prompt}],
+        model=model,
+        response_format={"type": "json_object"},
+    )
+
+    reply = response.choices[0].message.content
+    assert isinstance(reply, str)
+    return typing.cast(dict[str, str], json.loads(reply))
+
+
+def fetch_webpage(url: str) -> lxml.html.HtmlElement:
+    """Fetch webpage HTML and parse it."""
+    response = requests.get(url, headers={"User-Agent": USER_AGENT})
+    response.raise_for_status()
+    return lxml.html.fromstring(response.content)
+
+
+def webpage_to_text(root: lxml.html.HtmlElement) -> str:
+    """Convert parsed HTML into readable text content."""
+    root_copy = lxml.html.fromstring(lxml.html.tostring(root))
+
+    for script_or_style in root_copy.xpath("//script|//style"):
+        script_or_style.drop_tree()
+
+    text_maker = html2text.HTML2Text()
+    text_maker.ignore_links = False
+    text_maker.ignore_images = True
+    return text_maker.handle(lxml.html.tostring(root_copy, encoding="unicode"))
+
+
+def url_to_booking_text(url: str) -> str:
+    """Fetch a URL and convert it to source text for the model."""
+    return webpage_to_text(fetch_webpage(url))
+
+
+def booking_text_from_args(args: list[str]) -> str:
+    """Return booking text from a URL argument or stdin."""
+    if args:
+        if len(args) != 1:
+            raise SystemExit("Usage: generate-BOOKING-booking-yaml [URL]")
+        return url_to_booking_text(args[0])
+    return sys.stdin.read()
+
+
+def generate_booking_yaml(
+    booking_text: str, config: BookingConfig, model: str = "gpt-5.4"
+) -> str:
+    """Generate booking YAML from source text."""
+    prompt = build_prompt(booking_text, config)
+    return get_from_open_ai(prompt, model=model)[config.json_key]
+
+
+def datetime_from_yaml_value(value: typing.Any) -> datetime:
+    """Convert a YAML date/datetime/string value into a datetime."""
+    if isinstance(value, datetime):
+        return value
+    if isinstance(value, date):
+        return datetime.combine(value, datetime.min.time())
+    if isinstance(value, str):
+        parsed = datetime.fromisoformat(value)
+        return parsed
+    raise TypeError(f"Unsupported departure value: {value!r}")
+
+
+def first_departure(booking: dict[str, typing.Any], config: BookingConfig) -> datetime:
+    """Return the first departure datetime for a generated booking."""
+    if config.booking_type == "flight":
+        flights = booking["flights"]
+        assert isinstance(flights, list)
+        first_flight = flights[0]
+        assert isinstance(first_flight, dict)
+        return datetime_from_yaml_value(first_flight["depart"])
+
+    return datetime_from_yaml_value(booking["depart"])
+
+
+def comparable_departure(
+    booking: dict[str, typing.Any], config: BookingConfig
+) -> datetime:
+    """Return a timezone-naive departure datetime for sorting."""
+    return first_departure(booking, config).replace(tzinfo=None)
+
+
+def generated_bookings_from_yaml(yaml_text: str) -> list[dict[str, typing.Any]]:
+    """Parse generated booking YAML into a list of booking mappings."""
+    loaded = yaml.safe_load(yaml_text)
+    if isinstance(loaded, dict):
+        return [typing.cast(dict[str, typing.Any], loaded)]
+    if isinstance(loaded, list) and all(isinstance(item, dict) for item in loaded):
+        return typing.cast(list[dict[str, typing.Any]], loaded)
+    raise ValueError("Generated booking YAML must be a mapping or list of mappings.")
+
+
+def trip_key_position(booking: dict[str, typing.Any], config: BookingConfig) -> int:
+    """Return the preferred insertion position for the top-level trip key."""
+    keys = list(booking)
+    if config.booking_type == "flight":
+        if "booking_reference" in booking:
+            return keys.index("booking_reference") + 1
+        return 0
+
+    if "to" in booking:
+        return keys.index("to") + 1
+    if "from" in booking:
+        return keys.index("from") + 1
+    return 0
+
+
+def set_trip_key(
+    booking: dict[str, typing.Any], config: BookingConfig, trip_date: date
+) -> dict[str, typing.Any]:
+    """Set trip in the usual top-level position while preserving other key order."""
+    without_trip = {key: value for key, value in booking.items() if key != "trip"}
+    keys = list(without_trip)
+    position = trip_key_position(without_trip, config)
+    reordered: dict[str, typing.Any] = {}
+
+    for index, key in enumerate(keys):
+        if index == position:
+            reordered["trip"] = trip_date
+        reordered[key] = without_trip[key]
+
+    if "trip" not in reordered:
+        reordered["trip"] = trip_date
+
+    booking.clear()
+    booking.update(reordered)
+    return booking
+
+
+def build_trips(data_dir: Path) -> list[TripLike]:
+    """Build trips from personal data without importing agenda.trip at module load."""
+    trip_module = importlib.import_module("agenda.trip")
+    build_trip_list = typing.cast(
+        typing.Callable[..., list[TripLike]], trip_module.build_trip_list
+    )
+    return build_trip_list(data_dir=str(data_dir))
+
+
+def matching_trip_date(depart: datetime, data_dir: Path = PERSONAL_DATA_DIR) -> date:
+    """Find the trip grouping date for a departure, falling back to departure date."""
+    depart_date = depart.date()
+    matching_starts: list[date] = []
+
+    for trip in build_trips(data_dir):
+        trip_end = trip.end or trip.start
+        if trip.start <= depart_date <= trip_end:
+            matching_starts.append(trip.start)
+
+    if matching_starts:
+        return max(matching_starts)
+    return depart_date
+
+
+def add_trip_dates(
+    bookings: list[dict[str, typing.Any]],
+    config: BookingConfig,
+    data_dir: Path = PERSONAL_DATA_DIR,
+) -> None:
+    """Add the top-level trip key to generated booking mappings."""
+    for booking in bookings:
+        trip_date = matching_trip_date(first_departure(booking, config), data_dir)
+        set_trip_key(booking, config, trip_date)
+
+
+def dump_generated_bookings(bookings: list[dict[str, typing.Any]]) -> str:
+    """Dump only generated bookings for insertion into an existing YAML list."""
+    text = yaml.dump(bookings, sort_keys=False, allow_unicode=True)
+    return text.lstrip()
+
+
+def join_yaml_list_blocks(preamble: str, blocks: list[str], trailing: str = "") -> str:
+    """Join top-level YAML list blocks with a blank line between items."""
+    body = "\n\n".join(block.rstrip("\n") for block in blocks)
+    return preamble + body + "\n" + trailing
+
+
+def split_yaml_list_blocks(text: str) -> tuple[str, list[str], str]:
+    """Split a top-level YAML list into preamble, item blocks, and trailing text."""
+    lines = text.splitlines(keepends=True)
+    first_item = next(
+        (index for index, line in enumerate(lines) if line.startswith("- ")), None
+    )
+    if first_item is None:
+        return text, [], ""
+
+    item_starts = [
+        index
+        for index, line in enumerate(lines[first_item:], start=first_item)
+        if line.startswith("- ")
+    ]
+    blocks = [
+        "".join(lines[start:end])
+        for start, end in zip(item_starts, item_starts[1:] + [len(lines)])
+    ]
+    return "".join(lines[:first_item]), blocks, ""
+
+
+def existing_bookings_from_blocks(blocks: list[str]) -> list[dict[str, typing.Any]]:
+    """Parse split YAML item blocks into booking mappings."""
+    bookings = []
+    for block in blocks:
+        loaded = yaml.safe_load(block)
+        if not isinstance(loaded, list) or len(loaded) != 1:
+            raise ValueError("Could not parse existing booking block.")
+        item = loaded[0]
+        if not isinstance(item, dict):
+            raise ValueError("Existing booking block is not a mapping.")
+        bookings.append(typing.cast(dict[str, typing.Any], item))
+    return bookings
+
+
+def insertion_index(
+    existing_bookings: list[dict[str, typing.Any]],
+    new_bookings: list[dict[str, typing.Any]],
+    config: BookingConfig,
+) -> int:
+    """Return the chronological insertion index for generated bookings."""
+    new_depart = min(comparable_departure(booking, config) for booking in new_bookings)
+    for index, booking in enumerate(existing_bookings):
+        if comparable_departure(booking, config) > new_depart:
+            return index
+    return len(existing_bookings)
+
+
+def insert_booking_text(
+    existing_text: str,
+    new_yaml_text: str,
+    config: BookingConfig,
+) -> str:
+    """Insert generated booking YAML into an existing top-level YAML list."""
+    preamble, blocks, trailing = split_yaml_list_blocks(existing_text)
+    new_bookings = generated_bookings_from_yaml(new_yaml_text)
+    _, new_blocks, _ = split_yaml_list_blocks(dump_generated_bookings(new_bookings))
+    if len(new_blocks) != len(new_bookings):
+        raise ValueError("Could not split generated booking YAML into item blocks.")
+
+    existing_bookings = existing_bookings_from_blocks(blocks)
+
+    new_items = sorted(
+        zip(new_bookings, new_blocks),
+        key=lambda item: comparable_departure(item[0], config),
+    )
+    for booking, block in new_items:
+        insert_at = insertion_index(existing_bookings, [booking], config)
+        existing_bookings.insert(insert_at, booking)
+        blocks.insert(insert_at, block)
+
+    return join_yaml_list_blocks(preamble, blocks, trailing)
+
+
+def import_booking_yaml(
+    generated_yaml: str,
+    config: BookingConfig,
+    data_dir: Path = PERSONAL_DATA_DIR,
+) -> int:
+    """Add generated booking YAML to the configured personal-data file."""
+    bookings = generated_bookings_from_yaml(generated_yaml)
+    add_trip_dates(bookings, config, data_dir)
+    new_yaml = dump_generated_bookings(bookings)
+
+    yaml_path = data_dir / config.yaml_filename
+    existing_text = yaml_path.read_text()
+    updated_text = insert_booking_text(existing_text, new_yaml, config)
+    yaml_path.write_text(updated_text)
+    return len(bookings)
+
+
+def main_for_type(booking_type: str, argv: list[str] | None = None) -> int:
+    """CLI entrypoint for a specific booking type."""
+    parser = argparse.ArgumentParser(
+        description=(
+            f"Generate {booking_type} booking YAML from stdin or a URL and import it."
+        )
+    )
+    parser.add_argument("url", nargs="?", help="Booking URL to fetch")
+    parser.add_argument("--model", default=os.environ.get("OPENAI_MODEL", "gpt-5.4"))
+    parser.add_argument(
+        "--data-dir",
+        default=str(PERSONAL_DATA_DIR),
+        help="Directory containing personal-data YAML files.",
+    )
+    parser.add_argument(
+        "--print-only",
+        action="store_true",
+        help="Print generated YAML instead of editing the personal-data file.",
+    )
+    parsed = parser.parse_args(argv)
+
+    config = BOOKING_CONFIGS[booking_type]
+    args = [parsed.url] if parsed.url else []
+    booking_text = booking_text_from_args(args)
+    new_yaml = generate_booking_yaml(booking_text, config, model=parsed.model)
+    if parsed.print_only:
+        print(new_yaml)
+        return 0
+
+    count = import_booking_yaml(new_yaml, config, data_dir=Path(parsed.data_dir))
+    print(f"Imported {count} {booking_type} booking(s).")
+    return 0
+
+
+def train_main(argv: list[str] | None = None) -> int:
+    """CLI entrypoint for train booking YAML generation."""
+    return main_for_type("train", argv)
+
+
+def flight_main(argv: list[str] | None = None) -> int:
+    """CLI entrypoint for flight booking YAML generation."""
+    return main_for_type("flight", argv)
diff --git a/agenda/trip.py b/agenda/trip.py
index 2561094..0518b93 100644
--- a/agenda/trip.py
+++ b/agenda/trip.py
@@ -119,6 +119,47 @@ def get_unbooked_flight_origin_iata(
     return "LHR"
 
 
+UNBOOKED_RAIL_DESTINATIONS: dict[tuple[str, str], tuple[str, str]] = {
+    ("fr", "paris"): ("London St Pancras", "Paris Gare du Nord"),
+}
+
+
+def load_station_lookup(data_dir: str) -> dict[str, StrDict]:
+    """Load stations keyed by station name."""
+    stations = travel.parse_yaml("stations", data_dir)
+    return {station["name"]: station for station in stations}
+
+
+def get_unbooked_rail_route(item: StrDict, data_dir: str) -> StrDict | None:
+    """Return an assumed rail route for a conference without booked travel."""
+    location = item.get("location")
+    country = item.get("country")
+    if not isinstance(location, str) or not isinstance(country, str):
+        return None
+
+    station_names = UNBOOKED_RAIL_DESTINATIONS.get(
+        (country.casefold(), normalize_place_name(location))
+    )
+    if station_names is None:
+        return None
+
+    stations = load_station_lookup(data_dir)
+    from_station = stations.get(station_names[0])
+    to_station = stations.get(station_names[1])
+    if from_station is None or to_station is None:
+        return None
+
+    key = "_".join(["train"] + sorted([from_station["name"], to_station["name"]]))
+    route: StrDict = {"type": "train", "key": key}
+    geojson_filename = from_station.get("routes", {}).get(to_station["name"])
+    if geojson_filename:
+        route["geojson_filename"] = os.path.join("train_routes", geojson_filename)
+    else:
+        route["from"] = latlon_tuple(from_station)
+        route["to"] = latlon_tuple(to_station)
+    return route
+
+
 def load_travel(travel_type: str, plural: str, data_dir: str) -> list[StrDict]:
     """Read flight and train journeys."""
     items: list[StrDict] = travel.parse_yaml(plural, data_dir)
@@ -473,10 +514,10 @@ def conference_free_days(trip: Trip) -> dict[str, tuple[int, int]]:
         return {}
 
     def conf_attend_start(c: StrDict) -> date:
-        return typing.cast(date, as_date(c.get("attend_start") or c["start"]))
+        return as_date(c.get("attend_start") or c["start"])
 
     def conf_attend_end(c: StrDict) -> date:
-        return typing.cast(date, as_date(c.get("attend_end") or c["end"]))
+        return as_date(c.get("attend_end") or c["end"])
 
     sorted_confs = sorted(trip.conferences, key=conf_attend_start)
     result: dict[str, tuple[int, int]] = {}
@@ -634,6 +675,11 @@ def get_trip_routes(trip: Trip, data_dir: str) -> list[StrDict]:
 
     unbooked_routes = []
     for item in trip.conferences:
+        unbooked_rail_route = get_unbooked_rail_route(item, data_dir)
+        if unbooked_rail_route is not None:
+            unbooked_routes.append(unbooked_rail_route)
+            continue
+
         if item["country"] in {"gb", "be"}:  # not flying to Belgium
             continue
         destination_iata = preferred_airport_iata(item, airports)
@@ -870,7 +916,7 @@ def _trip_element_label(element: TripElement) -> str:
         return start_loc
     if isinstance(end_loc, str):
         return end_loc
-    return typing.cast(str, element.title)
+    return element.title
 
 
 def _trip_element_summary(trip: Trip, element: TripElement) -> str:
diff --git a/scripts/build_airport_yaml b/scripts/build_airport_yaml
new file mode 100755
index 0000000..cb7c9d6
--- /dev/null
+++ b/scripts/build_airport_yaml
@@ -0,0 +1,15 @@
+#!/usr/bin/python3
+
+import os
+import sys
+
+SCRIPT_PATH = os.path.realpath(__file__)
+SCRIPT_DIR = os.path.dirname(SCRIPT_PATH)
+REPO_ROOT = os.path.dirname(SCRIPT_DIR)
+if REPO_ROOT not in sys.path:
+    sys.path.insert(0, REPO_ROOT)
+
+from agenda.build_place_yaml import airport_main
+
+if __name__ == "__main__":
+    raise SystemExit(airport_main())
diff --git a/scripts/build_station_yaml b/scripts/build_station_yaml
new file mode 100755
index 0000000..9285a8f
--- /dev/null
+++ b/scripts/build_station_yaml
@@ -0,0 +1,15 @@
+#!/usr/bin/python3
+
+import os
+import sys
+
+SCRIPT_PATH = os.path.realpath(__file__)
+SCRIPT_DIR = os.path.dirname(SCRIPT_PATH)
+REPO_ROOT = os.path.dirname(SCRIPT_DIR)
+if REPO_ROOT not in sys.path:
+    sys.path.insert(0, REPO_ROOT)
+
+from agenda.build_place_yaml import station_main
+
+if __name__ == "__main__":
+    raise SystemExit(station_main())
diff --git a/scripts/generate-flight-booking-yaml b/scripts/generate-flight-booking-yaml
new file mode 100755
index 0000000..ba9c161
--- /dev/null
+++ b/scripts/generate-flight-booking-yaml
@@ -0,0 +1,15 @@
+#!/usr/bin/python3
+
+import os
+import sys
+
+SCRIPT_PATH = os.path.realpath(__file__)
+SCRIPT_DIR = os.path.dirname(SCRIPT_PATH)
+REPO_ROOT = os.path.dirname(SCRIPT_DIR)
+if REPO_ROOT not in sys.path:
+    sys.path.insert(0, REPO_ROOT)
+
+from agenda.generate_booking_yaml import flight_main
+
+if __name__ == "__main__":
+    raise SystemExit(flight_main())
diff --git a/scripts/generate-train-booking-yaml b/scripts/generate-train-booking-yaml
new file mode 100755
index 0000000..1c0a7ba
--- /dev/null
+++ b/scripts/generate-train-booking-yaml
@@ -0,0 +1,15 @@
+#!/usr/bin/python3
+
+import os
+import sys
+
+SCRIPT_PATH = os.path.realpath(__file__)
+SCRIPT_DIR = os.path.dirname(SCRIPT_PATH)
+REPO_ROOT = os.path.dirname(SCRIPT_DIR)
+if REPO_ROOT not in sys.path:
+    sys.path.insert(0, REPO_ROOT)
+
+from agenda.generate_booking_yaml import train_main
+
+if __name__ == "__main__":
+    raise SystemExit(train_main())
diff --git a/tests/test_build_place_yaml.py b/tests/test_build_place_yaml.py
new file mode 100644
index 0000000..9e181dd
--- /dev/null
+++ b/tests/test_build_place_yaml.py
@@ -0,0 +1,101 @@
+"""Tests for agenda.build_place_yaml."""
+
+from pathlib import Path
+
+import yaml
+
+from agenda import build_place_yaml
+
+
+def test_upsert_station_adds_new_station(tmp_path: Path) -> None:
+    """Station upsert should add a new station to stations.yaml."""
+    path = tmp_path / "stations.yaml"
+    path.write_text("""- name: London St Pancras
+  latitude: 51.531921
+  longitude: -0.126361
+  country: gb
+  wikidata: Q720102
+  routes: {}
+""")
+
+    replaced = build_place_yaml.upsert_station(
+        tmp_path,
+        {
+            "name": "Paris Gare du Nord",
+            "latitude": 48.8809,
+            "longitude": 2.3553,
+            "country": "fr",
+            "wikidata": "Q624511",
+            "routes": {},
+        },
+    )
+
+    stations = yaml.safe_load(path.read_text())
+    assert replaced is False
+    assert [station["name"] for station in stations] == [
+        "London St Pancras",
+        "Paris Gare du Nord",
+    ]
+    assert "\n\n- name: Paris Gare du Nord\n" in path.read_text()
+
+
+def test_upsert_station_replaces_existing_station(tmp_path: Path) -> None:
+    """Station upsert should replace an existing station with the same name."""
+    path = tmp_path / "stations.yaml"
+    path.write_text("""- name: Paris Gare du Nord
+  latitude: 0
+  longitude: 0
+  country: fr
+  wikidata: Q624511
+  routes: {}
+""")
+
+    replaced = build_place_yaml.upsert_station(
+        tmp_path,
+        {
+            "name": "Paris Gare du Nord",
+            "latitude": 48.8809,
+            "longitude": 2.3553,
+            "country": "fr",
+            "wikidata": "Q624511",
+            "routes": {},
+        },
+    )
+
+    stations = yaml.safe_load(path.read_text())
+    assert replaced is True
+    assert len(stations) == 1
+    assert stations[0]["latitude"] == 48.8809
+    assert "\n\n- name:" not in path.read_text()
+
+
+def test_upsert_airport_adds_mapping_entry(tmp_path: Path) -> None:
+    """Airport upsert should add a new IATA-keyed airport entry."""
+    path = tmp_path / "airports.yaml"
+    path.write_text("""LHR:
+  iata: LHR
+  name: Heathrow Airport
+  city: London
+  country: gb
+  latitude: 51.47
+  longitude: -0.4543
+  qid: Q8691
+""")
+
+    replaced = build_place_yaml.upsert_airport(
+        tmp_path,
+        {
+            "iata": "ORY",
+            "name": "Paris Orly Airport",
+            "city": "Paris Orly Airport",
+            "country": "fr",
+            "latitude": 48.723333,
+            "longitude": 2.379444,
+            "qid": "Q193353",
+        },
+    )
+
+    airports = yaml.safe_load(path.read_text())
+    assert replaced is False
+    assert list(airports) == ["LHR", "ORY"]
+    assert airports["ORY"]["country"] == "fr"
diff --git a/tests/test_generate_booking_yaml.py b/tests/test_generate_booking_yaml.py
new file mode 100644
index 0000000..51ff471
--- /dev/null
+++ b/tests/test_generate_booking_yaml.py
@@ -0,0 +1,187 @@
+"""Tests for agenda.generate_booking_yaml."""
+
+from dataclasses import dataclass
+from datetime import date
+from pathlib import Path
+
+import pytest
+import yaml
+
+from agenda import generate_booking_yaml
+
+
+@dataclass
+class FakeTrip:
+    """Small stand-in for agenda.types.Trip in matching tests."""
+
+    start: date
+    end: date | None
+
+
+def test_yaml_format_description_includes_train_spec() -> None:
+    """Train prompt docs should come from personal-data-yaml.md."""
+    description = generate_booking_yaml.yaml_format_description(
+        generate_booking_yaml.BOOKING_CONFIGS["train"]
+    )
+
+    assert "## General Rules" in description
+    assert "## Cross-File References" in description
+    assert "## `trains.yaml`" in description
+    assert "`operator`: booking/operator label" in description
+
+
+def test_build_prompt_uses_spec_and_keeps_trip_exclusion() -> None:
+    """The generated prompt should use the documented schema."""
+    prompt = generate_booking_yaml.build_prompt(
+        "Eurostar booking details",
+        generate_booking_yaml.BOOKING_CONFIGS["train"],
+        current_bookings="- operator: eurostar\n",
+    )
+
+    assert "Use this YAML format specification" in prompt
+    assert "## `trains.yaml`" in prompt
+    assert 'Exclude the top-level "trip" key' in prompt
+    assert "Eurostar booking details" in prompt
+
+
+def test_booking_text_from_args_fetches_url(monkeypatch: pytest.MonkeyPatch) -> None:
+    """URL arguments should be fetched instead of reading stdin."""
+    monkeypatch.setattr(
+        generate_booking_yaml,
+        "url_to_booking_text",
+        lambda url: f"fetched {url}",
+    )
+
+    assert generate_booking_yaml.booking_text_from_args(["https://example.com"]) == (
+        "fetched https://example.com"
+    )
+
+
+def test_matching_trip_date_uses_built_trip_end(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """Trip matching should use build_trip_list-derived end dates."""
+    monkeypatch.setattr(
+        generate_booking_yaml,
+        "build_trips",
+        lambda data_dir: [  # noqa: ARG005
+            FakeTrip(date(2026, 2, 6), date(2026, 2, 9)),
+            FakeTrip(date(2026, 3, 3), date(2026, 3, 5)),
+        ],
+    )
+
+    assert generate_booking_yaml.matching_trip_date(
+        generate_booking_yaml.datetime_from_yaml_value("2026-02-08 12:00:00+01:00"),
+        Path("/tmp/personal-data"),
+    ) == date(2026, 2, 6)
+
+
+def test_matching_trip_date_falls_back_to_departure_date(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """A booking outside known trips should use its first departure date."""
+    monkeypatch.setattr(
+        generate_booking_yaml, "build_trips", lambda data_dir: []  # noqa: ARG005
+    )
+
+    assert generate_booking_yaml.matching_trip_date(
+        generate_booking_yaml.datetime_from_yaml_value("2026-04-10 12:00:00+01:00"),
+        Path("/tmp/personal-data"),
+    ) == date(2026, 4, 10)
+
+
+def test_import_train_booking_adds_trip_and_inserts_chronologically(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """Generated train bookings should be written into trains.yaml in order."""
+    (tmp_path / "trains.yaml").write_text("""- operator: early
+  from: A
+  to: B
+  trip: 2026-02-01
+  depart: 2026-02-01 10:00:00+00:00
+  arrive: 2026-02-01 11:00:00+00:00
+  legs: []
+
+- operator: late
+  from: C
+  to: D
+  trip: 2026-02-10
+  depart: 2026-02-10 10:00:00+00:00
+  arrive: 2026-02-10 11:00:00+00:00
+  legs: []
+""")
+    monkeypatch.setattr(
+        generate_booking_yaml,
+        "matching_trip_date",
+        lambda depart, data_dir: date(2026, 2, 6),
+    )
+
+    count = generate_booking_yaml.import_booking_yaml(
+        """- operator: eurostar
+  from: London St Pancras
+  to: Brussels Midi
+  depart: 2026-02-06 15:04:00+00:00
+  arrive: 2026-02-06 18:12:00+01:00
+  legs: []
+""",
+        generate_booking_yaml.BOOKING_CONFIGS["train"],
+        data_dir=tmp_path,
+    )
+
+    written = yaml.safe_load((tmp_path / "trains.yaml").read_text())
+    assert count == 1
+    assert [item["operator"] for item in written] == ["early", "eurostar", "late"]
+    assert written[1]["trip"] == date(2026, 2, 6)
+    assert list(written[1]).index("trip") == 3
+    assert "\n\n- operator: eurostar\n" in (tmp_path / "trains.yaml").read_text()
+
+
+def test_import_flight_booking_adds_trip_and_inserts_chronologically(
+    tmp_path: Path,
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """Generated flight bookings should be written into flights.yaml in order."""
+    (tmp_path / "flights.yaml").write_text("""---
+- booking_reference: OLD
+  trip: 2026-02-01
+  flights:
+   - depart: 2026-02-01 10:00:00+00:00
+     from: BRS
+     to: AMS
+     flight_number: '1'
+     airline: U2
+
+- booking_reference: NEWER
+  trip: 2026-02-10
+  flights:
+   - depart: 2026-02-10 10:00:00+00:00
+     from: BRS
+     to: AMS
+     flight_number: '2'
+     airline: U2
+""")
+    monkeypatch.setattr(
+        generate_booking_yaml,
+        "matching_trip_date",
+        lambda depart, data_dir: date(2026, 2, 6),
+    )
+
+    count = generate_booking_yaml.import_booking_yaml(
+        """booking_reference: MID
+flights:
+  - depart: 2026-02-06 10:00:00+00:00
+    from: BRS
+    to: AMS
+    flight_number: '3'
+    airline: U2
+""",
+        generate_booking_yaml.BOOKING_CONFIGS["flight"],
+        data_dir=tmp_path,
+    )
+
+    written = yaml.safe_load((tmp_path / "flights.yaml").read_text())
+    assert count == 1
+    assert [item["booking_reference"] for item in written] == ["OLD", "MID", "NEWER"]
+    assert written[1]["trip"] == date(2026, 2, 6)
+    assert list(written[1]).index("trip") == 1
diff --git a/tests/test_trip.py b/tests/test_trip.py
index 69c0e6e..614d669 100644
--- a/tests/test_trip.py
+++ b/tests/test_trip.py
@@ -3,6 +3,7 @@
 from datetime import date
 
 import agenda.trip
+import pytest
 from agenda.types import Trip
 from web_view import app
 
@@ -101,3 +102,68 @@ def test_get_coordinates_and_routes_adds_unbooked_flight_airports() -> None:
         coord["name"] for coord in coordinates if coord["type"] == "airport"
     }
     assert airport_names == {"Heathrow Airport", "Paris Charles de Gaulle Airport"}
+
+
+def test_get_trip_routes_assumes_unbooked_paris_trip_is_by_train(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    """Paris conferences without booked travel should show rail, not flight."""
+    trip = Trip(
+        start=date(2026, 7, 20),
+        conferences=[
+            {
+                "name": "Paris Conf",
+                "location": "Paris",
+                "country": "fr",
+            }
+        ],
+    )
+    stations = [
+        {
+            "name": "London St Pancras",
+            "latitude": 51.531921,
+            "longitude": -0.126361,
+            "routes": {"Paris Gare du Nord": "London_St_Pancras_to_Paris_Gare_du_Nord"},
+        },
+        {
+            "name": "Paris Gare du Nord",
+            "latitude": 48.88111111111111,
+            "longitude": 2.355277777777778,
+            "routes": {"London St Pancras": "London_St_Pancras_to_Paris_Gare_du_Nord"},
+        },
+    ]
+
+    def fake_parse_yaml(name: str, data_dir: str) -> object:
+        if name == "stations":
+            return stations
+        if name == "airports":
+            return {
+                "LHR": {
+                    "name": "Heathrow Airport",
+                    "latitude": 51.47,
+                    "longitude": -0.45,
+                },
+                "CDG": {
+                    "name": "Paris Charles de Gaulle Airport",
+                    "city": "Paris",
+                    "country": "fr",
+                    "latitude": 49.01,
+                    "longitude": 2.55,
+                },
+            }
+        raise AssertionError(f"unexpected YAML load: {name}")
+
+    monkeypatch.setattr(agenda.trip.travel, "parse_yaml", fake_parse_yaml)
+    monkeypatch.setattr(
+        agenda.trip, "load_flight_destination_rules", lambda _data_dir: []
+    )
+
+    routes = agenda.trip.get_trip_routes(trip, "/tmp/personal-data")
+
+    assert routes == [
+        {
+            "type": "train",
+            "key": "train_London St Pancras_Paris Gare du Nord",
+            "geojson_filename": "train_routes/London_St_Pancras_to_Paris_Gare_du_Nord",
+        }
+    ]