MONDAY I'm in Barbados. Sailing here from Gran Canaria underlines the fundamental weakness of the risk assessment I used to advocate in school. You identify risks, take every precaution and it still goes pear-shaped.
Everything pointed to gentle winds, warm seas and star-filled nights - not gales and fierce squalls. But that's what has happened. The anchorage abounds with horror stories. Risk assessment is a way to make gambling seem res-pectable. But you can still lose your shirt on a dead cert.
TUESDAY Even retired education officers twitch when schools are mentioned. School uniforms are mandatory in Barbados -no uniform, no school. The kids look smart, but the local press reports discipline problems in classrooms, suggesting that universal uniformity is not the whole answer.
WEDNESDAY Sailing to Admiralty Bay, a 100-mile hop, I meet one of the cruise liners that now infest the Caribbean. Their passengers seem to buy a new T-shirt on a different island each day, but everywhere is so close these ships sail in circles to give the illusion of cruising. I overtake this one.
THURSDAY Admiralty Bay is a picture postcard tropical anchorage, but the local news smacks of home. Parents and their children (in school uniform) demonstrate to highlight poor school conditions; leaking roofs and tatty toilets we know all about, but termites eating floors and furniture?
When he opens a new school later in the week, the minister for education here carefully lists multi-million-dollar school-building projects. Elsewhere, St Vincent teachers accuse their government of "not negotiating in good faith", while the government claims the teachers are "negotiating in bad faith". Both sides promise action - so much in common, so far apart.
On Bequia I meet the island's last harpooner, who throws harpoons at whales from a boat rowed by eight men. Sometimes the whales win, dragging the boat and its crew underwater. Living history.
FRIDAY My route to Grenada takes me over Kick-em-Jenny, an undersea volcano thinking of erupting. If it does, there'll be 20 minutes' warning before tidal waves rush across the Caribbean. This topic is not covered in the RYA's Yachtmaster syllabus, but it does give the cruise liners a chance to sell "Poseidon Adventure" T-shirts.
I plan to hide in the Tobago Cays but I suspect that's another fine plan that will not survive contact with reality.
Alastair Buchan is a former education officer from Sunderland who has sailed single-handed to the Caribbean