They are both islands, making the license plate game a challenge.
They are about the same size (Cuba=109,000 sq. km. vs. Iceland=103,000 sq. km.)
Cuba has many more people (11,400,000 vs. 327,000).
Their capitol cities are both on the ocean.
Cuba works totally on cash, two kinds in fact. You could survive a trip in Iceland with only your Visa card (we did take money out of an ATM to see what it looked like).
They are both undergoing major construction to prepare for tourists.
Neither one has a McDonald's or a Starbucks, but Iceland does have other American food chains (such as Dominos and Subway).
Cuba has very old cars. Iceland has new ones.
Both I would highly recommend seeing.
It is funny how we draw upon our past when we visit new people and places and make comparisons. I met a woman I liked instantly, even before I realized she reminds me of a friend. The city of Reykjavik reminded me of Portland, Oregon with the mountains in the background, the outdoors culture, and the quirkiness of the locals. Despite living in a place that hardly ever sees the sun, everyone we met was friendly and outgoing.
I had other thoughts while in Iceland. As I think of them, I'll add them to this post.