So far, I've had the opportunity to visit the territories marked in dark blue on the map above.
You can build a non-interactive version of your map of countries visited - It's easy and fun.
A World Nomads offers one of the best and most complete travel insurance recommended by National Geographic and Lonely Planet. Other excellent and cheaper option is IATI Seguros, which has no age limit and allows multivariate insurance (including long-term travel) to any destination in the world. It's the insurance I use in my travels.