Should tunnels be connected from an ISP to an internal data center?

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Generally speaking, I recommend initiating connections from a higher security environment to a lower security environment. In either case, you'll get the confidentiality protection afforded by the secure tunnel, but you gain a slight advantage of reduced complexity by connecting to the less secure environment from the more secure one.

You'll need to create a firewall rule allowing inbound access on the firewall protecting the destination environment. You should definitely create a point-to-point rule that limits inbound access to the source IP address of the other tunnel endpoint; regardless, this rule still allows some extra degree of inbound access. When you have the choice of adding complexity to a less sensitive or more sensitive environment, you should opt to add it to the less sensitive environment.

Remember that complexity is the enemy of security: it makes verification of security controls more difficult and increases the likelihood of a configuration error. Adding the inbound rule to the less secure environment increases the complexity of that environment rather than the more secure one.

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