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Most drilling operations in deep water are performed in Dynamic Positioning (DP) mode. In harsh environments and shallow water conditions, thruster assisted position mooring configurations are often the preferred choice as the mooring lines provide an extra help to counteract the environmental loads. Drilling operations, both in pure DP or thruster-assisted position mooring modes, are limited by the ability of the vessel to maintain position and heading within the required accuracy. In addition, the motion in heave, roll and pitch must be within predefined limits. These limits vary between the type of operation to be performed. For example, reconnecting the low marine riser package has much stricter motion limitations compared to logging or drilling through riser operations. All these operations need to be carefully planned; and having estimate in advance of the vessel motion and station-keeping performance could be of vital importance, also considering planned maintenance. The aim of this paper is to share experiences in planning DP drilling operations by using cloud-based time-domain simulations performed with a digital twin of a semi-submersible drilling rig. A digital twin is a virtual representation of an asset, used from early design through building and operations, maintained and easily accessible throughout its lifecycle. A digital twin can replicate many aspects of the asset; in the case of planning DP drilling operations, our digital twin includes time-domain models for running simulations and predicting the vessel motion.