I would never believe it if I didn't see it myself, so I am posting a picture:
As you can see, my first-generation iPad fits in my Small Cafe Bag!
OK so it's not the fancy Risretto, and it's not as roomy as the Medium Cafe Bag. But it fits! I can even fit my keys, wallet, and a couple other items in the bag!
So if you were curious, yes it fits! It's snug. But if you like the compactness of the Small Cafe Bag and assumed the iPad was too big for it, give it a try yourself!