I have some experience in a
Pearson Vanguard 33. In my opinion, 3 people onboard for an overnight or longer voyage should the maximum if you want to still be friends when the voyage is over. When tacking or jibing, the tiller sweeps the
cockpit, requiring at least one crew
member to step over it (energetically). More than 3 in the cockpit gets to be a real "goat rope". The
interior volume is small for a 33. With 5 people on board it would be crowded as HELL, it would be difficult to impossible to get any rest or sleep as the other crew would keep you awake
cooking, eating, using the
head, etc, etc. "Sardines in a can" is a pretty accurate description of what it would be like. Personally, if I were going to make this voyage, I'd prefer to do it with only one other crew
member (preferably female) besides myself. The Vanguard is an easy
boat to sail. 2 able-bodied people should have no problem. I would MUCH prefer to go single-handed than to suffer being stuck onboard such a
small boat with 4 other people. Highly unlikely to be an enjoyable experience. I'm not trying to discourage you at all. By all means: "GO!!!". Just don't expect to enjoy yourself with so many people crammed in such a small space for several days.