It would be easier to answer your query if you had mentioned the type/size of boat and whether you're talking about ham SSB or marine SSB or both.
The easiest way to put a HF/SSB rig on the air with RELIABLE long-distance communication is to construct one or more vertical dipole antennas. See my posts on constructing a marine dipole: Gallery :: Constructing a Marine Dipole Antenna
and on tuning a marine dipole antenna:
SSCA Discussion Board :: View topic - How to Tune a Marine Dipole Antenna
A vertical dipole antenna will outperform any other seagoing antenna you can put on a sailboat. Period. They are, however, limited to single-band operation for transmitting; they receive well on all bands.
For many years when chartering, I carried a small HF transceiver with big alligator clips on the power cord, and a dipole antenna. It took only a few minutes after stepping aboard to be QRV (ready) to transmit on the ham bands, and to talk with friends around the world.
Good luck on your delivery.
S/V Born Free