Crossing the bar should not be regarded as something to dread but it should be regarded with respect and to such ends a trip across the bar should be treated as a voyage and planned in accordance with SOLAS principles.
First of all the boat needs to be sea worthy and fit for the job, with an alternative power supply or method, with no unattended maintenance tasks or repairs that may affect the ability of the boat and its crew to meet the demands of the trip. There should be adequate means of navigation, including a chart, tide table and all the gear associated with chart navigation. A hand bearing compass is vital for checking where you are and ensuring you have confidence in your navigation. Putting the club Way Points (WP) into a GPS does NOT constitute adequate preparation for a trip over the bar.