Yes, you can make loop trips with CREATE A CALCULATED ROUTE (using waypoints).
1. Create a "custom place" for each place you want to visit, as you did, saving each one.
2. Click the "Select Marker" button (to the right of the "Add Waypoint" text), and
3. Click the marker for the place you want to visit. Do (2) and (3) for each custom place.
4. Now you have a list of waypoints to visit. (You need to click them in the order you want the route to go, and you’ll see them on the “my current waypoints” list in the "My Current Waypoints" just to the right of the "Add Waypoint" button.)
5. Add the start & finish addresses – your home for both, in "Start Address" and "End Address".
6. Click “find route from addresses"...
7. It will draw the route. If the RTA Maps program thinks a loop is the shortest way, it will draw a loop.
Try this!
And let us know, how it goes for you.
Mark