For me, I'd either say Cyrodiil, Morrowind or Skyrim. Mostly because IRL I'd say I most closely resemble (out of TES races) a Nord/ Imperial. I come from a cold place, and live in a somewhat... Imperial-like area. (Central England) and I admire the Dunmer.

I'd sit for a drink in the Bannered Mare, go up North and have a few pints in the Bannered Mare before high-fiving several Dunmer of Morrowind. In that order.

Morrowind obviously, I'd join House Telvanni.