What (and how long ago) is your previous sailing experience?
Are you taking any medication?
Do you have any allergies?
Are you a strong swimmer?
Are you expecting any payment?
Are you affected by seasickness?
Will trip reports and voyage forms be filed?
Who is the shore-based contact to monitor progress?
What form will a passage plan take?
Can you supply several references?
Will drugs or alcohol be carried on board?
Will firearms be carried?
Will wet gear be provided?
Will PFDs and tethers be provided?
What is the protocol for the wearing of PFDs and tethers?
Is there a grab bag on board? Can it be used for wallet, medications, spare glasses, etc.?
Where is the storage space for clothes and wet gear?
How comprehensive is the first aid kit?
What is the watchkeeping plan?
How skilled are you at recognizing vessel lights at night?
How will the work and duties on board be divided?
Is there any gear on board that the crew is not permitted to use?
What restrictions are there on the crew in terms of what they can't do on board?
Are men permitted to urinate over the side? (They shouldn't be.)
What knots can you tie?
What is your navigation skill level?
What food do you like or dislike?
How will the cooking arrangements work?
What stores are on board and are any restricted?
What is the state of the emergency equipment? Have the service periods expired?
Will there be time before departure to familiarize with safety equipment and storm tactics?
Will there be time before departure to familiarize with all the ship's gear and sails?
What measures will be taken to prevent falling overboard?
Will crew overboard retrieval be practiced before departure?
How old is the rigging wire?
Is the boat clean and tidy? What is the state of the bilge?
Have likely weather patterns been considered?
What are the weather parameters for a departure?
What is the motoring range of the boat and at what speed/RPM?
Discuss and plan for the big six--collision, fire, flooding, grounding, injury, and sickness.