Technology

The ISP will always know the IP you're connecting to. Encrypted DNS might get you slightly more privacy for sites using shared IPs like with Cloudflare. But in a lot of cases, there's only 1 website per IP, so the ISP still knows where you're browsing. A VPN solves this by routing all traffic through the VPNs IP first. But you can still be tracked just the same by the VPN and to an extent, the VPNs ISP.

DoH & DoT still leak the domain name (and of course IP address) you're connecting to. The domain name leak can be solved by Encrypted Client Hello but that's still a draft and not turned on for many servers.

Yes and no.

Modern HTTPS connections send the URL you are connecting to in the initial hello, so the remote webserver knows what security certificate to use when you connect. A lot of web servers host multiple sites, especially for smaller webpages, and so it doesn't assume that since you connected to that specific webserver, that you're connecting to the site that the webserver is hosting, even if it's only hosting a single site.

This can leak the data to anyone sniffing the traffic.

You can also determine some traffic by IP address, this is for larger web services like Facebook, youtube and other sites of similar size. They load balance groups of IPs for their traffic, all are serving the same data. So if you connect to an IP that's owned by Facebook, for example, then your actions can be easily derived.

Since the connection is still secured by TLS, the content can't be deciphered, but the location you are going to absolutely can.

It really depends on a lot of factors.

You can substitute "Tor" for "VPN" in the above and be largely correct. Tor acts like a VPN, but every packet goes through multiple hops, so an attacker would need to do quite a bit of work (i.e. compromise multiple nodes) to link traffic to you.

So:

• TLS (https) - network owner can't see specific content, but can determine what sites you visit
• VPN - network owner can't tell what sites you visit, but can tell you're on a VPN; VPN can tell what sites you visit, but not specific content
• Tor - network owner can't tell what sites you visit, but can tell you're using Tor; Tor exit node operators can see what sites people using it visit, but can't attribute it to an individual user w/o a sophisticated attack

In most cases, TLS is perfectly fine, provided you make sure to not click through any TLS errors (i.e. certificate can't be validate => probable middle-man attack), and using a VPN is probably overkill. A VPN protects you from that middle-man attack, but honestly, if you're savvy enough to use a VPN, you're probably savvy enough to not get compromised by a middle-man attack. Likewise if you use Tor, you're probably savvy enough to not get compromised by a middle-man attack.

That said, I fully support using Tor and VPNs, I just won't go so far as to say someone is dumb for not using them on public Wi-Fi. Make sure you're connecting to a real Wi-Fi service and don't disable TLS protections and you're probably fine, from a security perspective. If you're likely to be targeted by a government agency, Tor is the bare minimum of what you should use.