20 miles down the coast is not a "long" trip by any stretch, but depending on the path,.. it could be tretiourious...
there are many required items on sea races (like the tybe 500, and others).. this would be a good place to start on what gear to carry...
http://www.tybee500.com/n…tybee_nor.pdf?1242081088
8. Safety Equipment
8.1 US Coast Guard (USCG) approved life preservers will be worn by each sailor while
racing and each boat will have a minimum of one USCG approved throwable device
aboard while racing. All life preservers will be in reasonably new, undamaged condition.
8.2 Each sailing crewmember will have, secured to his person, a small knife, a whistle,
a 406 MHz EPIRB (with a valid & current NOAA registration and a battery with valid
date stamp), a personal safety strobe, a waterproof flashlight, and a safety line that can
be readily attached to the boat. Note: 121 & 243 MHz epirbs are no longer acceptable.
Proof of NOAA Registration of the 406 MHz EPIRB must be provided to the Principal
Race Officer.
8.3 Each boat will have a waterproof VHF radio, marine grade compass, three day /
night flares in date, charts comprising the entire coastal area of the race for that day,
and a cellular phone in a transparent, waterproof bag. The Race committee will be provided
with the number of the cellular phone. Communication between sailing and
ground team members is permitted during the race; however, communication with any
vessels on the water is not permitted.
Ground crew and family "Flight plans" are a good thing as well...
and i like to try and sail with "on shore" breezes when possible so my bloated, blue, dead body will wash up on shore (vs. out to sea as shark bait)... :)(or your "broken" cat can drift to shore, not to japan)
that being said.... anything out of your "comfort zone" should be well planned, practiced, and you really better be able to repair ANYTHING that can break on such a trip...