In addition to some self-sufficiency waterproof food and fresh water, we find it handy to have some other things when we're doing such sailing.
1. A couple of waterproof single smoke and ariel flares is awful handy just in case.
2. One paddle is better than a daggerboard or paddling surfboard style and we wished we had two when the sun went down and we still had a long way to go w/o wind.
3. A fully charged cell phone,
4. LED divers flashlight and a couple of chemical lights and a whistle for each person,
5. submersible GPS,
6. a chart of the area,
7. small waterproof strobe,
8. VHF submersible radio,
9. A few extra batteries in a water proof container with your cell phone is good insurance,
10. A small sea anchor was handy and on one occasion staying put was a good thing and being bow to seas rather than beam on made life better than otherwise.
11. Suitable clothing for expected conditions and something so you can be warm and seen if it turns into an unexpected night-time thing.
12. Give someone who is reliable a copy of your float plan and some instructions if they don't hear back from you at a prearranged time.
13. Give big boats and especially ships a very wide berth. They may or may not actually see you and they don't turn on a dime nor do they stop very well. It is always surprising how fast they are actually going. Just because your a sail boat with the right of way, doesn't mean it will go that way ...and bigger always has the right of way and is more forgiving in a crash than is smaller.
14. PFDs for each whether or not your wearing wet or dry suits.
We were caught out once or twice on such sails and found these kinds of things very useful.
Most of this kind of stuff can be simply lanyard and/or tie to our PFDs so it is easily available for each person whether you or your crew is on the boat or unexpectedly in the water.
On a couple of occasions, we intended a day sail and it turned into a late sail going until nearly midnight. One went unexpectedly until 10 or so the next AM.
Group sailing is great but we generally have often become separated...sometimes never seeing the other boats or they each other.
Assuming what someone else may or may not do is a poor substitute for proper preparation, planning, communication and contingencies. Don't rely totally on someone else to pull your bacon out of the fire.
Expect the best, plan and prepare for the worst, then enjoy.
