Need recommendations for a two week trip thru Spain & Portugal

Two weeks really isn’t all that long. The Costa Del Sol is out of the way for where you want to end up and you can get the same vibe along the Algarve, or even up by Lisbon in Cascais or Estoril. How you’re getting around will impact what you visit. With starting in Madrid and ending in Lisbon, I’d head to Extremadura. It is an overlooked region of Spain. It May, temperatures shouldn’t be too terribly high. Some cities between those locations are Toledo, Trujillo, Mérida, Cáceres, and Guadalupe. If heading to the Algarve, then Zarfa and Sevilla are possibilities. From Sevilla you’d need to head west. Huelva is not on most tourists’ radar. The Algarve starts once you cross the border. There are plenty of lesser sites to visit in Extremadura; too many to list here. One could easily spend a month in that region.

You simply need to do some research and select places of interest to you and that might suit your retirement, whatever you mean by that.

Agreeing with jaimeelsabio, 2 weeks is short to cover that territory for general tourism. For sinking in to get vibes for retirement locations it seems insufficient— research could offer more focus.

Considerations might include the area’s population demographics (more Brits than Spaniards in some of the coastal areas), visa possibilities, tax implications, costs of living (especially real estate), transportation options/accessibility.