diff --git a/upath/core.py b/upath/core.py
index 3aaa93af..0e7b48ff 100644
--- a/upath/core.py
+++ b/upath/core.py
@@ -1355,7 +1355,7 @@ def relative_to(  # type: ignore[override]
             if self.__class__ is not other.__class__:
                 raise ValueError(
                     "incompatible protocols:"
-                    f" {self._protocol!r} != {other._protocol!r}"
+                    f" {self.protocol!r} != {other.protocol!r}"
                 )
             if self.storage_options != other.storage_options:
                 raise ValueError(
@@ -1371,7 +1371,7 @@ def relative_to(  # type: ignore[override]
             raise ValueError(f"{self!s} is not in the subpath of {other!s}")
         else:
             rel = copy(self)
-            rel._relative_base = str(other)
+            rel._relative_base = other.path
             return rel
 
     def is_relative_to(self, other, /, *_deprecated) -> bool:  # type: ignore[override]
diff --git a/upath/extensions.py b/upath/extensions.py
index fabc86a6..48966cbd 100644
--- a/upath/extensions.py
+++ b/upath/extensions.py
@@ -370,6 +370,8 @@ def relative_to(  # type: ignore[override]
         *_deprecated,
         walk_up=False,
     ) -> Self:
+        if isinstance(other, ProxyUPath):
+            other = other.__wrapped__
         return self._from_upath(
             self.__wrapped__.relative_to(other, *_deprecated, walk_up=walk_up)
         )
diff --git a/upath/implementations/sftp.py b/upath/implementations/sftp.py
index 018b8e8b..ff924a52 100644
--- a/upath/implementations/sftp.py
+++ b/upath/implementations/sftp.py
@@ -36,6 +36,19 @@ def __init__(
             **storage_options: Unpack[SFTPStorageOptions],
         ) -> None: ...
 
+    @property
+    def path(self) -> str:
+        path = super().path
+        if len(path) > 1:
+            return path.removesuffix("/")
+        return path
+
+    def __str__(self) -> str:
+        path_str = super().__str__()
+        if path_str.startswith(("ssh:///", "sftp:///")):
+            return path_str.removesuffix("/")
+        return path_str
+
     def iterdir(self) -> Iterator[Self]:
         if not self.is_dir():
             raise NotADirectoryError(str(self))
diff --git a/upath/implementations/smb.py b/upath/implementations/smb.py
index 685f4539..7adaade1 100644
--- a/upath/implementations/smb.py
+++ b/upath/implementations/smb.py
@@ -40,6 +40,19 @@ def __init__(
             **storage_options: Unpack[SMBStorageOptions],
         ) -> None: ...
 
+    @property
+    def path(self) -> str:
+        path = super().path
+        if len(path) > 1:
+            return path.removesuffix("/")
+        return path
+
+    def __str__(self) -> str:
+        path_str = super().__str__()
+        if path_str.startswith("smb:///"):
+            return path_str.removesuffix("/")
+        return path_str
+
     def mkdir(
         self,
         mode: int = 0o777,
diff --git a/upath/tests/cases.py b/upath/tests/cases.py
index 56bb0141..82bd136d 100644
--- a/upath/tests/cases.py
+++ b/upath/tests/cases.py
@@ -655,3 +655,9 @@ def test_move_into_memory(self, clear_fsspec_memory_cache):
         assert target.exists()
         assert target.read_text() == content
         assert not source.exists()
+
+    def test_relative_to(self):
+        base = self.path
+        child = self.path / "folder1" / "file1.txt"
+        relative = child.relative_to(base)
+        assert str(relative) == "folder1/file1.txt"
diff --git a/upath/tests/implementations/test_data.py b/upath/tests/implementations/test_data.py
index 5b1fe92e..db59cb10 100644
--- a/upath/tests/implementations/test_data.py
+++ b/upath/tests/implementations/test_data.py
@@ -283,3 +283,7 @@ def test_move_memory(self, clear_fsspec_memory_cache):
     @pytest.mark.skip(reason="DataPath does not support unlink")
     def test_move_into_memory(self, clear_fsspec_memory_cache):
         pass
+
+    @pytest.mark.skip(reason="DataPath does not support relative_to")
+    def test_relative_to(self):
+        pass