You're making the typical newbie mistake of looking for crystal-clear one-size-fits-all universal advice. In practice, it all depends. Different tools provide different benefits while making different trade-offs. If you don't know whether you need Tails, read up on what Tails is and what it aims to achieve. Some people may benefit from a VPN (often for the same reasons they may benefit from a bridge), and for others it's pointless (but never harmful IMNSHO).
Don't rely on the advice of strangers on the internet. Real security comes from understanding your specific situations and the tools available to you.
I know this answer fricking sucks and doesn't help you, but anonymity is hard. If you don't feel like you have any specific personal situation you need to evaluate tools against, just install Tor Browser on the computer you are currently using and be happy – it works and is designed to meet most regular needs.
Due to Apple's policies, there are no good ones. The least bad one is called Onion Browser and is recommended by the Tor Project.