Just for fun…
There is a puddle…
…on an island (Ryan Island)…
…in a lake (Siskiwit Lake)…
…on an island (Isle Royale)…
…in a lake (Lake Superior)…
…on a landmass (the Americas)…
…surrounded by water (oceans of the world).
Can you do better?
(By the way, I found this neat island on my own while playing with Google Earth. After looking for the name of this island on the Internet I found that Ryan Island has the distinction of being the largest island on the largest lake, on the largest island, in the largest (freshwater) lake in the world.)
David Richeson: Division by Zero 
Great post. Reminds me of the trivia question asking which state has the lowest highest point…or the state with the highest lowest point…or you can do countries for an international flair. And at least make a few guesses before googling the answer. :)
My favorite along these lines: what state has the lowest recorded high temperature? The highest recorded low temperature?
It turns out that the answer to both questions is…. Hawaii. The record high is 100 degrees F (tied with Alaska, actually), the record low is 12 degrees F.
Been there, done that. There are two other candidates in the Great Lakes.
http://is.gd/dpPuL
Wow. 1994. Excellent. Thanks for the link.
How about islands on one of three lakes on an island in a lake on an island (kinda) in a lake on a continent in the ocean (credit for this one goes probably goes to Farley Mowat):
http://maps.google.com/?ie=UTF8&ll=61.24902,-99.408031&spn=0.016452,0.037551&t=h&z=15
The water/land boundaries are so fractal-like in that region that it is hard to tell what’s what! Thanks.
This may also be of interest:
http://pining.blogspot.com/2010/07/enclave-within-enclave-within-enclave.html
Wow, that is crazy! I’m definitely going to have to look into it more. Thanks for sharing.