diff --git a/CHANGES/1382.feature.rst b/CHANGES/1382.feature.rst
new file mode 120000
index 000000000..62a3dbc9b
--- /dev/null
+++ b/CHANGES/1382.feature.rst
@@ -0,0 +1 @@
+1340.feature.rst
\ No newline at end of file
diff --git a/yarl/_path.py b/yarl/_path.py
index f7995ddc5..838aa94cb 100644
--- a/yarl/_path.py
+++ b/yarl/_path.py
@@ -2,6 +2,7 @@
 
 from collections.abc import Sequence
 from contextlib import suppress
+from itertools import chain
 from pathlib import PurePosixPath
 
 
@@ -54,11 +55,11 @@ def calculate_relative_path(target: str, base: str) -> str:
     target_path = PurePosixPath(target)
     base_path = PurePosixPath(base)
 
-    if not base[-1] == "/":
+    if base[-1] != "/":
         base_path = base_path.parent
 
-    for step, path in enumerate((base_path, *base_path.parents)):
-        if target_path.is_relative_to(path):
+    for step, path in enumerate(chain((base_path,), base_path.parents)):
+        if path == target_path or path in target_path.parents:
             break
         elif path.name == "..":
             raise ValueError(f"'..' segment in {str(base_path)!r} cannot be walked")