diff --git a/backend/server/chat/tests.py b/backend/server/chat/tests.py
index f59b03ae..7b3aa43a 100644
--- a/backend/server/chat/tests.py
+++ b/backend/server/chat/tests.py
@@ -120,6 +120,15 @@ class ChatAgentToolSharedTripAccessTests(TestCase):
 
 
 class ChatViewSetToolValidationBoundaryTests(TestCase):
+    def test_trip_context_destination_summary_normalizes_to_first_segment(self):
+        self.assertEqual(
+            ChatViewSet._trip_context_search_location(
+                "A; B; +1 more",
+                ["Fallback City"],
+            ),
+            "A",
+        )
+
     def test_dates_is_required_matches_required_param_short_circuit(self):
         self.assertTrue(
             ChatViewSet._is_required_param_tool_error({"error": "dates is required"})
@@ -467,3 +476,84 @@ class ChatViewSetSearchPlacesClarificationTests(APITransactionTestCase):
         self.assertEqual(first_call_kwargs.get("category"), "food")
         self.assertEqual(second_call_kwargs.get("category"), "food")
         self.assertEqual(second_call_kwargs.get("location"), "Rome, Italy")
+
+    @patch("chat.views.execute_tool")
+    @patch("chat.views.stream_chat_completion")
+    @patch("integrations.utils.auto_profile.update_auto_preference_profile")
+    def test_trip_context_retry_uses_normalized_summary_destination_for_search_places(
+        self,
+        _mock_auto_profile,
+        mock_stream_chat_completion,
+        mock_execute_tool,
+    ):
+        user = User.objects.create_user(
+            username="chat-summary-retry-user",
+            email="chat-summary-retry-user@example.com",
+            password="password123",
+        )
+        self.client.force_authenticate(user=user)
+
+        conversation_response = self.client.post(
+            "/api/chat/conversations/",
+            {"title": "Summary Destination Retry Test"},
+            format="json",
+        )
+        self.assertEqual(conversation_response.status_code, 201)
+        conversation_id = conversation_response.json()["id"]
+
+        async def first_stream(*args, **kwargs):
+            yield 'data: {"tool_calls": [{"index": 0, "id": "call_1", "type": "function", "function": {"name": "search_places", "arguments": "{}"}}]}\n\n'
+            yield "data: [DONE]\n\n"
+
+        async def second_stream(*args, **kwargs):
+            yield 'data: {"content": "I found places in Paris."}\n\n'
+            yield "data: [DONE]\n\n"
+
+        mock_stream_chat_completion.side_effect = [first_stream(), second_stream()]
+        mock_execute_tool.side_effect = [
+            {"error": "location is required"},
+            {"results": [{"name": "Louvre Museum"}]},
+        ]
+
+        response = self.client.post(
+            f"/api/chat/conversations/{conversation_id}/send_message/",
+            {
+                "message": "Find top attractions",
+                "destination": "Paris, France; Rome, Italy; +1 more",
+            },
+            format="json",
+        )
+
+        self.assertEqual(response.status_code, 200)
+        chunks = [
+            chunk.decode("utf-8")
+            if isinstance(chunk, (bytes, bytearray))
+            else str(chunk)
+            for chunk in response.streaming_content
+        ]
+        payload_lines = [
+            chunk.strip()[len("data: ") :]
+            for chunk in chunks
+            if chunk.strip().startswith("data: ")
+        ]
+        json_payloads = [
+            json.loads(payload) for payload in payload_lines if payload != "[DONE]"
+        ]
+
+        self.assertTrue(any("tool_result" in payload for payload in json_payloads))
+        self.assertTrue(
+            any(
+                payload.get("content") == "I found places in Paris."
+                for payload in json_payloads
+            )
+        )
+        self.assertFalse(
+            any(
+                "specific location" in payload.get("content", "").lower()
+                for payload in json_payloads
+            )
+        )
+
+        self.assertEqual(mock_execute_tool.call_count, 2)
+        second_call_kwargs = mock_execute_tool.call_args_list[1].kwargs
+        self.assertEqual(second_call_kwargs.get("location"), "Paris, France")
diff --git a/backend/server/chat/views/__init__.py b/backend/server/chat/views/__init__.py
index 948af457..92186082 100644
--- a/backend/server/chat/views/__init__.py
+++ b/backend/server/chat/views/__init__.py
@@ -199,8 +199,31 @@ class ChatViewSet(viewsets.ModelViewSet):
         )
 
     @staticmethod
-    def _trip_context_search_location(destination, itinerary_stops):
+    def _normalize_trip_context_destination(destination):
         destination_text = (destination or "").strip()
+        if not destination_text:
+            return ""
+
+        if ";" not in destination_text:
+            if re.fullmatch(r"\+\d+\s+more", destination_text, re.IGNORECASE):
+                return ""
+            return destination_text
+
+        for segment in destination_text.split(";"):
+            segment_text = segment.strip()
+            if not segment_text:
+                continue
+
+            if re.fullmatch(r"\+\d+\s+more", segment_text, re.IGNORECASE):
+                continue
+
+            return segment_text
+
+        return ""
+
+    @classmethod
+    def _trip_context_search_location(cls, destination, itinerary_stops):
+        destination_text = cls._normalize_trip_context_destination(destination)
         if destination_text:
             return destination_text
 
@@ -309,8 +332,6 @@ class ChatViewSet(viewsets.ModelViewSet):
         itinerary_stops = []
         if collection_name:
             context_parts.append(f"Trip: {collection_name}")
-        if destination:
-            context_parts.append(f"Destination: {destination}")
         if start_date and end_date:
             context_parts.append(f"Dates: {start_date} to {end_date}")
 
@@ -369,6 +390,8 @@ class ChatViewSet(viewsets.ModelViewSet):
         trip_context_location = self._trip_context_search_location(
             destination, itinerary_stops
         )
+        if trip_context_location:
+            context_parts.append(f"Destination: {trip_context_location}")
         prior_user_messages = list(
             conversation.messages.filter(role="user")
             .order_by("-created_at")