Some personal and where to start

While struggling to get the latest update to Windows 10 to install (me and a few thousand others) I realized I only had 3 GB of free space on a 120 GB SSD. So having bought a new 500 GB SSD, I now have a free 120 GB drive to play with. I am a newbie only to Linux, not in real life, being the far side of retirement, so I think it is time to make the jump into Linux. From what I have read disc space is not going to be an issue, but what can I put in it that I can dual-boot with Windows? Is Ubuntu the place to start? I like a Windows icon based system not command line. And I will probably have a go with trying Wine with some of my Windows applications. Does Wine work with Ububtu?

Someone point me in a direction to start please. And where do I find all of these things to install?