Being near a computer that uses Tor should be fine as long as it isn't tied to you in specific. Even using Tor once or twice is probably fine, although never using Tor from a location or device or IP address that can be linked to you is always the best bet. One of the main things you need to worry about is simply getting the Tor software in the first place, an attacker could very well just monitor the Tor project website and see who all downloads Tor. A lot more people download Tor than regularly use it though. In many cases your usage pattern of Tor will leak to an attacker who can monitor the Tor directory authorities, but your usage pattern will not leak to an attacker who monitors the Tor download site. I don't like using remote virtual machines. The people who own the remote server can spy on your traffic as it passes through. Plus unless you use Tor to connect to the remote machine you are not going to be getting the cool encryption features of Tor. Almost all VPNs are extremely weak to website fingerprinting attacks because they don't pad their encrypted packets to all be the same size. Tor pads packets to 512 bytes and this significantly distorts fingerprints. Website fingerprinting attacks have in some cases identified that traffic has a 98%+ probability of being a certain preidentified website, even though the traffic is encrypted and can not be decrypted without the proper keys or a currently infeasible amount of computing power. I think the best anyone has done against Tor is 60%. Tor kind of tries to disguise its traffic as SSL. Although it still sticks out. For example all packets are 512 bytes. It also used to have a unique parameter with its SSL implementation but they changed that after some country (forgot which) started using it to identify connections to bridges. Tor traffic still sticks out but it has gotten more and more disguised over the past few years, and currently it requires a significant amount of resources to passively scan large amounts of traffic looking for Tor traffic. If it was easy to do bridges wouldn't work to by pass the great firewall of China, they would just block all Tor traffic.