To start, you gotta use a search engine other than Google, Yahoo, or Bing. Try: https://duckduckgo.com/ Doesn't track any user data. Also, using a VPN blocks websites from tracking your location. Try: https://www.tunnelbear.com/ Then, you can start here: https://www.reddit.com/r/deepweb/ ///
Tor Browser. there is a sort of an index wiki page with links to the most known sites in the deep dark web. You can go from there.
and even better, to use another machine (leave your regular computer up-and-running - maybe downloading some big file), with a different OS, such as TAILS (which will force you through the TOR network anyway), plus a VPN. Or if you're really concerned about privacy & security, try QubesOS.