diff --git a/docs/tutorial/multiple-values/multiple-options-with-multiple-values.md b/docs/tutorial/multiple-values/multiple-options-with-multiple-values.md
new file mode 100644
index 0000000000..65d924f397
--- /dev/null
+++ b/docs/tutorial/multiple-values/multiple-options-with-multiple-values.md
@@ -0,0 +1,37 @@
+# Multiple options with multiple values
+
+For when simple doesn't quite cut it, you may also declare a *CLI option* that takes several values of different types and can be used multiple times.
+
+For this, we use the standard Python `list` and declare it as a list of `tuple`:
+
+{* docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_an_py310.py hl[9] *}
+
+Just as before, the types internal to the `tuple` define the type of each value in the tuple.
+
+## Check it
+
+<div class="termy">
+
+```console
+$ python main.py
+
+Congratulations, you're debt-free!
+
+// Now let's borrow some money.
+$ python main.py --borrow 2.5 Mark
+
+Borrowed 2.50 from Mark
+
+Total borrowed: 2.50
+
+// And, of course, it may be used multiple times
+$ python main.py --borrow 2.5 Mark --borrow 5.25 Sean --borrow 1.75 Wade
+
+Borrowed 2.50 from Mark
+Borrowed 5.25 from Sean
+Borrowed 1.75 from Wade
+
+Total borrowed: 9.50
+```
+
+</div>
diff --git a/docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_an_py310.py b/docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_an_py310.py
new file mode 100644
index 0000000000..45dbbaf61e
--- /dev/null
+++ b/docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_an_py310.py
@@ -0,0 +1,22 @@
+from typing import Annotated
+
+import typer
+
+app = typer.Typer()
+
+
+@app.command()
+def main(borrow: Annotated[list[tuple[float, str]], typer.Option()] = []):
+    if not borrow:
+        print("Congratulations, you're debt-free!")
+        raise typer.Exit(0)
+    total = 0.0
+    for amount, person in borrow:
+        print(f"Borrowed {amount:.2f} from {person}")
+        total += amount
+    print()
+    print(f"Total borrowed: {total:.2f}")
+
+
+if __name__ == "__main__":
+    app()
diff --git a/docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_py310.py b/docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_py310.py
new file mode 100644
index 0000000000..382a466625
--- /dev/null
+++ b/docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_py310.py
@@ -0,0 +1,20 @@
+import typer
+
+app = typer.Typer()
+
+
+@app.command()
+def main(borrow: list[tuple[float, str]] = typer.Option([])):
+    if not borrow:
+        print("Congratulations, you're debt-free!")
+        raise typer.Exit(0)
+    total = 0.0
+    for amount, person in borrow:
+        print(f"Borrowed {amount:.2f} from {person}")
+        total += amount
+    print()
+    print(f"Total borrowed: {total:.2f}")
+
+
+if __name__ == "__main__":
+    app()
diff --git a/mkdocs.yml b/mkdocs.yml
index 3cf3b5c1f7..cebb8aea63 100644
--- a/mkdocs.yml
+++ b/mkdocs.yml
@@ -146,6 +146,7 @@ nav:
           - tutorial/multiple-values/index.md
           - tutorial/multiple-values/multiple-options.md
           - tutorial/multiple-values/options-with-multiple-values.md
+          - tutorial/multiple-values/multiple-options-with-multiple-values.md
           - tutorial/multiple-values/arguments-with-multiple-values.md
       - tutorial/prompt.md
       - tutorial/progressbar.md
diff --git a/pyproject.toml b/pyproject.toml
index 990366bd3e..9d37018a3a 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -228,6 +228,7 @@ ignore = [
 # Default mutable data structure
 "docs_src/options_autocompletion/tutorial006_an_py310.py" = ["B006"]
 "docs_src/multiple_values/multiple_options/tutorial002_an_py310.py" = ["B006"]
+"docs_src/multiple_values/multiple_options_with_multiple_values/tutorial001_an_py310.py" = ["B006"]
 "docs_src/options_autocompletion/tutorial007_an_py310.py" = ["B006"]
 "docs_src/options_autocompletion/tutorial008_an_py310.py" = ["B006"]
 "docs_src/options_autocompletion/tutorial009_an_py310.py" = ["B006"]
diff --git a/tests/test_tutorial/test_multiple_values/test_multiple_options_with_multiple_values/__init__.py b/tests/test_tutorial/test_multiple_values/test_multiple_options_with_multiple_values/__init__.py
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/test_tutorial/test_multiple_values/test_multiple_options_with_multiple_values/test_tutorial001.py b/tests/test_tutorial/test_multiple_values/test_multiple_options_with_multiple_values/test_tutorial001.py
new file mode 100644
index 0000000000..305ae6791b
--- /dev/null
+++ b/tests/test_tutorial/test_multiple_values/test_multiple_options_with_multiple_values/test_tutorial001.py
@@ -0,0 +1,77 @@
+import importlib
+import subprocess
+import sys
+from types import ModuleType
+
+import pytest
+from typer.testing import CliRunner
+
+runner = CliRunner()
+
+
+@pytest.fixture(
+    name="mod",
+    params=[
+        pytest.param("tutorial001_py310"),
+        pytest.param("tutorial001_an_py310"),
+    ],
+)
+def get_mod(request: pytest.FixtureRequest) -> ModuleType:
+    module_name = f"docs_src.multiple_values.multiple_options_with_multiple_values.{request.param}"
+    mod = importlib.import_module(module_name)
+    return mod
+
+
+def test_main(mod: ModuleType):
+    result = runner.invoke(mod.app)
+    assert result.exit_code == 0
+    assert "Congratulations, you're debt-free!" in result.output
+
+
+def test_borrow_1(mod: ModuleType):
+    result = runner.invoke(mod.app, ["--borrow", "2.5", "Mark"])
+    assert result.exit_code == 0
+    assert "Borrowed 2.50 from Mark" in result.output
+    assert "Total borrowed: 2.50" in result.output
+
+
+def test_borrow_many(mod: ModuleType):
+    result = runner.invoke(
+        mod.app,
+        [
+            "--borrow",
+            "2.5",
+            "Mark",
+            "--borrow",
+            "5.25",
+            "Sean",
+            "--borrow",
+            "1.75",
+            "Wade",
+        ],
+    )
+    assert result.exit_code == 0
+    assert "Borrowed 2.50 from Mark" in result.output
+    assert "Borrowed 5.25 from Sean" in result.output
+    assert "Borrowed 1.75 from Wade" in result.output
+    assert "Total borrowed: 9.50" in result.output
+
+
+def test_invalid_borrow(mod: ModuleType):
+    result = runner.invoke(mod.app, ["--borrow", "2.5"])
+    assert result.exit_code != 0
+    # TODO: when deprecating Click 7, remove second option
+
+    assert (
+        "Option '--borrow' requires 2 arguments" in result.output
+        or "--borrow option requires 2 arguments" in result.output
+    )
+
+
+def test_script(mod: ModuleType):
+    result = subprocess.run(
+        [sys.executable, "-m", "coverage", "run", mod.__file__, "--help"],
+        capture_output=True,
+        encoding="utf-8",
+    )
+    assert "Usage" in result.stdout
diff --git a/typer/main.py b/typer/main.py
index f4f21bb844..6b95f5283b 100644
--- a/typer/main.py
+++ b/typer/main.py
@@ -1671,10 +1671,24 @@ def get_click_param(
         # Handle Tuples and Lists
         if lenient_issubclass(origin, list):
             main_type = get_args(main_type)[0]
-            assert not get_origin(main_type), (
-                "List types with complex sub-types are not currently supported"
-            )
+            list_origin = get_origin(main_type)
+            list_origin_is_tuple = lenient_issubclass(list_origin, tuple)
+            if not list_origin_is_tuple:
+                assert not list_origin, (
+                    "List types with complex sub-types are not currently supported"
+                )
             is_list = True
+            if list_origin_is_tuple:
+                types = []
+                for type_ in get_args(main_type):
+                    assert not get_origin(type_), (
+                        "List[Tuple] types with complex Tuple sub-types are not "
+                        "currently supported"
+                    )
+                    types.append(
+                        get_click_type(annotation=type_, parameter_info=parameter_info)
+                    )
+                parameter_type = tuple(types)
         elif lenient_issubclass(origin, tuple):
             types = []
             for type_ in get_args(main_type):
@@ -1692,6 +1706,8 @@ def get_click_param(
         )
     convertor = determine_type_convertor(main_type)
     if is_list:
+        if list_origin_is_tuple:
+            convertor = generate_tuple_convertor(get_args(main_type))
         convertor = generate_list_convertor(
             convertor=convertor, default_value=default_value
         )