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We are currently using Web 8.1 version of CMS with around 80+ websites. We are considering upgrading to latest version. My understanding of migration path for on premise is as follows.
web 8.1 (current version) --> sites 9 --> Tridion sites 9.5 --> Tridion sites 9.6
But, my question is instead of on prem, if we want move to Tridion sites cloud, What would be the migration path? Can we directly go to cloud after upgrading to sites 9?
There are obviously a lot of caveats and factors before I can tell you "definitely yes". Our approach is to always move to the cloud on the latest version, meaning that you would have to upgrade to 9.6.
What I tend to see customers doing is to upgrade as part of the move to cloud, i.e. RWS could assist in the initial upgrade to 9.6 on premise, then handle the move to cloud.
This is oversimplifying the process a lot, as it really depends on how customized your deployment is, what model you're using for Cloud (Content Management only or full Stack), etc.
With disclaimers as I don't do these myself and every project can be different
What I suspect would be the correct migration path here would be to get a copy of your database upgraded all the way to 9.6 (following the DB migration path of 8.1 -> 8.5 -> 9 -> 9.6) and then testing it with your extensions and configurations. Please note that I am talking about a DB upgrade, not a full environment upgrade that would go through all these versions. Based on the results then potentially extensions and web applications would have to be modified to cope with the new version, and moved to Cloud.
The official documentation also shares some clues: https://docs.rws.com/986894/123145/tridion-sites-9-6-main-documentation/versions-from-which-you-can-upgrade
Just to add a little to Nuno's correct answer above.
"Can we directly go to cloud after upgrading to sites 9?" As I understand it, like most cloud solutions of anything, there's a priority on not lagging being on legacy versions wherever possible.
And, like most cloud solutions of anything, it's often going to be simpler to upgrade/test/deploy on a more local environment (access, security, bandwidth etc. etc.).
Given this - I'm not sure that you would ever want to join a cloud solution with anything but the latest version of anything that you can.
Also, if you do have extensions note that you will need to ensure that these can be deployed using the AddOn framework as (again, as I understand it) the Cloud Ops team will make the final (to PROD) deployment of AddOns etc. - so there's no phaffing with the odd file here and there :)
