diff --git a/src/components/drag/Droppable.js b/src/components/drag/Droppable.js
index c51c25e..facc108 100644
--- a/src/components/drag/Droppable.js
+++ b/src/components/drag/Droppable.js
@@ -4,11 +4,7 @@ import { useDroppable } from "@dnd-kit/core";
 function Droppable({ id, children, disabled }) {
   const { setNodeRef } = useDroppable({ id, disabled });
 
-  return (
-    <div style={{ width: "100%", height: "100%" }} ref={setNodeRef}>
-      {children}
-    </div>
-  );
+  return <div ref={setNodeRef}>{children}</div>;
 }
 
 Droppable.defaultProps = {
diff --git a/src/components/drag/Sortable.js b/src/components/drag/Sortable.js
deleted file mode 100644
index 24f6783..0000000
--- a/src/components/drag/Sortable.js
+++ /dev/null
@@ -1,30 +0,0 @@
-import React from "react";
-import { useSortable } from "@dnd-kit/sortable";
-
-function Sortable({ id, children }) {
-  const {
-    attributes,
-    listeners,
-    setNodeRef,
-    isDragging,
-    transform,
-    transition,
-  } = useSortable({ id });
-
-  const style = {
-    cursor: "pointer",
-    opacity: isDragging ? 0.25 : undefined,
-    transform:
-      transform && `translate3d(${transform.x}px, ${transform.y}px, 0px)`,
-    zIndex: isDragging ? 100 : undefined,
-    transition,
-  };
-
-  return (
-    <div ref={setNodeRef} style={style} {...listeners} {...attributes}>
-      {children}
-    </div>
-  );
-}
-
-export default Sortable;
diff --git a/src/components/drag/SortableTile.js b/src/components/drag/SortableTile.js
new file mode 100644
index 0000000..b8f3be1
--- /dev/null
+++ b/src/components/drag/SortableTile.js
@@ -0,0 +1,65 @@
+import React from "react";
+import { Box } from "theme-ui";
+import { useDroppable } from "@dnd-kit/core";
+import { useSortable } from "@dnd-kit/sortable";
+
+function Sortable({ id, children, showDropGutter }) {
+  const {
+    attributes,
+    listeners,
+    isDragging,
+    transition,
+    setDroppableNodeRef,
+    setDraggableNodeRef,
+  } = useSortable({ id });
+  const { setNodeRef: setGroupNodeRef } = useDroppable({
+    id: `__group__${id}`,
+  });
+
+  const dragStyle = {
+    cursor: "pointer",
+    opacity: isDragging ? 0.25 : undefined,
+    zIndex: isDragging ? 100 : undefined,
+    transition,
+  };
+
+  // Sort div left aligned
+  const sortDropStyle = {
+    position: "absolute",
+    left: "-5px",
+    top: 0,
+    width: "2px",
+    height: "100%",
+    borderRadius: "2px",
+  };
+
+  // Group div center aligned
+  const groupDropStyle = {
+    position: "absolute",
+    top: 0,
+    left: "50%",
+    width: "1px",
+    height: "100%",
+  };
+
+  return (
+    <Box style={{ position: "relative" }}>
+      <Box
+        ref={setDraggableNodeRef}
+        style={dragStyle}
+        {...listeners}
+        {...attributes}
+      >
+        {children}
+      </Box>
+      <Box
+        ref={setDroppableNodeRef}
+        style={sortDropStyle}
+        bg={showDropGutter && "primary"}
+      />
+      <Box ref={setGroupNodeRef} style={groupDropStyle} />
+    </Box>
+  );
+}
+
+export default Sortable;
diff --git a/src/components/drag/SortableTiles.js b/src/components/drag/SortableTiles.js
index 4527ad8..338113f 100644
--- a/src/components/drag/SortableTiles.js
+++ b/src/components/drag/SortableTiles.js
@@ -7,11 +7,16 @@ import {
   TouchSensor,
   useSensor,
   useSensors,
+  closestCenter,
 } from "@dnd-kit/core";
 import { SortableContext, arrayMove } from "@dnd-kit/sortable";
 import { animated, useSpring, config } from "react-spring";
 
-function SortableTiles({ groups, onGroupChange, renderTile, children }) {
+import { combineGroups } from "../../helpers/select";
+
+import SortableTile from "./SortableTile";
+
+function SortableTiles({ groups, onGroupChange, renderTile, renderTiles }) {
   const mouseSensor = useSensor(MouseSensor, {
     activationConstraint: { delay: 250, tolerance: 5 },
   });
@@ -22,14 +27,29 @@ function SortableTiles({ groups, onGroupChange, renderTile, children }) {
   const sensors = useSensors(mouseSensor, touchSensor);
 
   const [dragId, setDragId] = useState();
+  const [overId, setOverId] = useState();
 
-  function handleDragStart({ active }) {
+  function handleDragStart({ active, over }) {
     setDragId(active.id);
+    setOverId(over?.id);
+  }
+
+  function handleDragMove({ over }) {
+    setOverId(over?.id);
   }
 
   function handleDragEnd({ active, over }) {
     setDragId();
-    if (active && over && active.id !== over.id) {
+    setOverId();
+    if (!active || !over) {
+      return;
+    }
+
+    if (over.id.startsWith("__group__")) {
+      return;
+    }
+
+    if (active.id !== over.id) {
       const oldIndex = groups.findIndex((group) => group.id === active.id);
       const newIndex = groups.findIndex((group) => group.id === over.id);
       onGroupChange(arrayMove(groups, oldIndex, newIndex));
@@ -37,18 +57,41 @@ function SortableTiles({ groups, onGroupChange, renderTile, children }) {
   }
 
   const dragBounce = useSpring({
-    transform: !!dragId ? "scale(1.05)" : "scale(1)",
+    transform: !!dragId ? "scale(0.9)" : "scale(1)",
     config: config.wobbly,
   });
 
+  const overGroupId =
+    overId && overId.startsWith("__group__") && overId.slice(9);
+
   return (
     <DndContext
       onDragStart={handleDragStart}
+      onDragMove={handleDragMove}
       onDragEnd={handleDragEnd}
       sensors={sensors}
+      collisionDetection={closestCenter}
     >
       <SortableContext items={groups}>
-        {children}
+        {renderTiles(
+          groups.map((group) => (
+            <SortableTile
+              id={group.id}
+              key={group.id}
+              showDropGutter={overId === group.id}
+            >
+              {dragId && overGroupId === group.id && group.id !== dragId
+                ? // If over a group render a preview of that group
+                  renderTile(
+                    combineGroups(
+                      group,
+                      groups.find((group) => group.id === dragId)
+                    )
+                  )
+                : renderTile(group)}
+            </SortableTile>
+          ))
+        )}
         {createPortal(
           <DragOverlay dropAnimation={null}>
             {dragId && (
diff --git a/src/components/map/MapTiles.js b/src/components/map/MapTiles.js
index 9c815b2..f630e59 100644
--- a/src/components/map/MapTiles.js
+++ b/src/components/map/MapTiles.js
@@ -10,7 +10,6 @@ import MapTileGroup from "./MapTileGroup";
 import Link from "../Link";
 import FilterBar from "../FilterBar";
 
-import Sortable from "../drag/Sortable";
 import SortableTiles from "../drag/SortableTiles";
 
 import useResponsiveLayout from "../../hooks/useResponsiveLayout";
@@ -69,7 +68,7 @@ function MapTiles({
     setHasMapState(_hasMapState);
   }, [selectedGroupIds, maps, mapStates, groups]);
 
-  function groupToMapTile(group) {
+  function renderTile(group) {
     if (group.type === "item") {
       const map = maps.find((map) => map.id === group.id);
       const isSelected = selectedGroupIds.includes(group.id);
@@ -107,12 +106,8 @@ function MapTiles({
 
   const multipleSelected = selectedGroupIds.length > 1;
 
-  return (
-    <SortableTiles
-      groups={groups}
-      onGroupChange={onMapsGroup}
-      renderTile={groupToMapTile}
-    >
+  function renderTiles(tiles) {
+    return (
       <Box sx={{ position: "relative" }}>
         <FilterBar
           onFocus={() => onTileSelect()}
@@ -142,11 +137,7 @@ function MapTiles({
             columns={layout.gridTemplate}
             onClick={() => onTileSelect()}
           >
-            {groups.map((group) => (
-              <Sortable id={group.id} key={group.id}>
-                {groupToMapTile(group)}
-              </Sortable>
-            ))}
+            {tiles}
           </Grid>
         </SimpleBar>
         {databaseDisabled && (
@@ -205,7 +196,16 @@ function MapTiles({
           </Flex>
         )}
       </Box>
-    </SortableTiles>
+    );
+  }
+
+  return (
+    <SortableTiles
+      groups={groups}
+      onGroupChange={onMapsGroup}
+      renderTile={renderTile}
+      renderTiles={renderTiles}
+    />
   );
 }
 
diff --git a/src/components/token/TokenTiles.js b/src/components/token/TokenTiles.js
index 29a70e4..cb3c9d2 100644
--- a/src/components/token/TokenTiles.js
+++ b/src/components/token/TokenTiles.js
@@ -11,7 +11,6 @@ import TokenTileGroup from "./TokenTileGroup";
 import Link from "../Link";
 import FilterBar from "../FilterBar";
 
-import Sortable from "../drag/Sortable";
 import SortableTiles from "../drag/SortableTiles";
 
 import useResponsiveLayout from "../../hooks/useResponsiveLayout";
@@ -49,7 +48,7 @@ function TokenTiles({
     setAllTokensVisisble(selectedTokens.every((token) => !token.hideInSidebar));
   }, [selectedGroupIds, tokens, groups]);
 
-  function groupToTokenTile(group) {
+  function renderTile(group) {
     if (group.type === "item") {
       const token = tokens.find((token) => token.id === group.id);
       const isSelected = selectedGroupIds.includes(group.id);
@@ -102,12 +101,8 @@ function TokenTiles({
     }
   }
 
-  return (
-    <SortableTiles
-      groups={groups}
-      onGroupChange={onTokensGroup}
-      renderTile={groupToTokenTile}
-    >
+  function renderTiles(tiles) {
+    return (
       <Box sx={{ position: "relative" }}>
         <FilterBar
           onFocus={() => onTileSelect()}
@@ -136,11 +131,7 @@ function TokenTiles({
             columns={layout.gridTemplate}
             onClick={() => onTileSelect()}
           >
-            {groups.map((group) => (
-              <Sortable id={group.id} key={group.id}>
-                {groupToTokenTile(group)}
-              </Sortable>
-            ))}
+            {tiles}
           </Grid>
         </SimpleBar>
         {databaseDisabled && (
@@ -199,7 +190,16 @@ function TokenTiles({
           </Flex>
         )}
       </Box>
-    </SortableTiles>
+    );
+  }
+
+  return (
+    <SortableTiles
+      groups={groups}
+      onGroupChange={onTokensGroup}
+      renderTile={renderTile}
+      renderTiles={renderTiles}
+    />
   );
 }
 
diff --git a/src/helpers/select.js b/src/helpers/select.js
index 4b577d5..45263fa 100644
--- a/src/helpers/select.js
+++ b/src/helpers/select.js
@@ -1,4 +1,5 @@
 import { useEffect, useState } from "react";
+import { v4 as uuid } from "uuid";
 import Fuse from "fuse.js";
 
 import { groupBy, keyBy } from "./shared";
@@ -135,6 +136,30 @@ export function handleItemSelect(
   }
 }
 
+/**
+ * @typedef GroupItem
+ * @property {string} id
+ * @property {"item"} type
+ */
+
+/**
+ * @typedef GroupContainer
+ * @property {string} id
+ * @property {"group"} type
+ * @property {GroupItem[]} items
+ * @property {string} name
+ */
+
+/**
+ * @typedef {GroupItem|GroupContainer} Group
+ */
+
+/**
+ * Transform an array of group ids to their groups
+ * @param {string[]} groupIds
+ * @param {Group[]} groups
+ * @return {Group[[]}
+ */
 export function groupsFromIds(groupIds, groups) {
   const groupsByIds = keyBy(groups, "id");
   const filteredGroups = [];
@@ -144,6 +169,11 @@ export function groupsFromIds(groupIds, groups) {
   return filteredGroups;
 }
 
+/**
+ * Get all items from a group including all sub groups
+ * @param {Group} group
+ * @return {GroupItem[]}
+ */
 function getGroupItems(group) {
   if (group.type === "group") {
     let groups = [];
@@ -156,6 +186,13 @@ function getGroupItems(group) {
   }
 }
 
+/**
+ * Transform an array of groups into their assosiated items
+ * @param {Group[]} groups
+ * @param {any[]} allItems
+ * @param {string} itemKey
+ * @returns {any[]}
+ */
 export function itemsFromGroups(groups, allItems, itemKey = "id") {
   const allItemsById = keyBy(allItems, itemKey);
   const groupedItems = [];
@@ -168,3 +205,28 @@ export function itemsFromGroups(groups, allItems, itemKey = "id") {
 
   return groupedItems;
 }
+
+/**
+ * Combine two groups
+ * @param {Group} a
+ * @param {Group} b
+ * @returns {GroupContainer}
+ */
+export function combineGroups(a, b) {
+  if (a.type === "item") {
+    return {
+      id: uuid(),
+      type: "group",
+      items: [a, b],
+      name: "",
+    };
+  }
+  if (a.type === "group") {
+    return {
+      id: a.id,
+      type: "group",
+      items: [...a.items, b],
+      name: a.name,
+    };
+  }
+}