Abstract Future deepwater drilling in Trinidad and Tobago will definitely present enormous challenges. During the period 1999 to 2003, eight deepwater wells were drilled in deepwater acreage. None of these wells found hydrocarbon in economic quantities although abundant reserves have been found in the shelf area (< 1000 meters water depth). The data from these wells would be useful for further deepwater and ultra deepwater drilling in Trinidad. To date, no wells have been drilled in our ultra deepwater acreage but seismic acquisition and processing has been undertaken. Thus lessons learned from the first deepwater campaign will definitely propel the way forward for further exploration works in deeper waters. We have to adapt our operations to accommodate the problems associated with our first phase of deepwater drilling in our area. This paper will look at the approaches we should adapt in the next phase of deepwater drilling. Some of these issues include rig selection, well location, well design and planning, environmental studies (wind, wave, climate etc.) and shallow hazard assessment. The key learnings from previous deepwater drilling events are useful in future operation in Trinidad and Tobago.