Using Area Type Tool successfully when font size is small compared to grid size

I'm trying to make a calendar.  I'm using an object (split into grid) for the "background", to be able to control fill/stroke.  I'm using the Area Type Tool (also split into grid) on top of that for filling in the dates/text.  This worked brilliantly for my yearly view where the date is centered in the grid box and is nearly as large as the square it occupies.  However, on my monthly view, where I want a much smaller number in the upper left corner of the calendar square, I encounter a situation where when I hit "enter", the cursor moves BELOW the number within the same cell (instead of to the next cell).   In fact, when I hit "enter" a second time, the cursor moves down again.  So it looks like it wants to have three lines of text within that cell when using that font size.  The only workaround I have found at this time it to enter my number, then just hit "enter" "enter" to end up in the next cell.  Is there a better way to achieve the same result without having to have 30+ separate text boxes, one for each date?  Thanks in advance for any advice!