Hi,
Yes you are correct, Y-DNA can trace further back in time, thousands of years in fact.
As you probably already know, only males can take Y-DNA tests & it traces a man's father's line, his grandfather, gt grandfather etc etc.
Autosomal DNA tests by comparison can be taken by males & females and reach back around 500 years or so - they test all ancestral lines of the family tree and are cheaper to buy.
There is lots of helpful info on the Rootschat DNA board -
https://www.rootschat.com/forum/ancestral-family-tree-dna-testing/I did a search on the FTDNA website for the surname Winn/Wynn and there is a Y-DNA surname project for Winn (+ variants) - see these links:
https://www.familytreedna.com/groups/winn/abouthttps://www.familytreedna.com/public/winn?iframe=yresultsThere are 440 members of the Winn/Wynn surname project which is pretty good. If you are male & only interested in your direct paternal line of Winn then a Y-DNA test from FTDNA is worth a shot.
As long as there are no non-paternity events in your paternal line back to the 1700s hopefully your DNA should match one or more members of this project.
An Autosomal DNA test from: Ancestry/MyHeritage/LivingDNA/23andme may bring some near or distant cousin matches on the Winn/Wynn line which might also help.