driftwood is bad. that stuff rips your keel straight off. i was lucky i avoided it when i did. i sure hope i don't meet any of that stuff in my galleon.
floating goods are tiny. you really need an eagle's eye to spot them at times. if you meet some stuff, and it's not upwind when using realistic sailing mode, strike your sails. then, scout around with your spyglass until you find it. this is tricky, because the goods sometimes get hidden behind the waves. then just go for it. lifeboats work the same way, as well as native rafts.
i don't know how long it takes to sail from oxbay to redmond, but i guess it should take one and a half or two game-days, thus a maximum of 6 real hours without speeding up the game. speeding up the game it should take 2 hours, though that's a complete guess. using directsail really takes a long time. the shortest voyage is from guadeloupe to falaise de fleur, taking 20 to 30 minutes, 15 if you're lucky.