Best places for a cycling adventure

Hi all, my brother and I are looking for a place to do a 5ish-day cycling adventure this winter or spring. He’s in DC and we’re open to travel, ideally someplace where my family could also come and have fun in the sun while we’re out on the road. I know @Francqlife did a Canary Islands camp which seems like it would check a lot of boxes. Any other suggestions or experiences folks would recommend? Thanks!

On an unrelated note, my Cervélo Caledonia 5 had a creak that would never go away so the company warrantied the frame and I’ll be getting a Soloist in a few weeks time. Swapping out the black matte for gold dust. Should be fun!

You might want to look into the various cycle tours Bicycle Breeze offers in Cuba. Much closer than the Canary Islands, and non-cycling family members are catered for. Disclaimer: I have not done one of their tours but I want to! and Book the Cuba bicycle tour of your dreams - Cycling tours in Cuba