First of all, I usually head back to the Caribbean in mid October, just after Canadian Thanksgiving. It's still sort-of hurricane season. The old Mariner's poem about hurricanes, that started "June - too soon" and ended "October - All over", doesn't appear to be the current viewpoint. October has seen many late season storms - Wilma in late October 2005 being the most famous. Wilma was the most intense hurricane ever-recorded and the 22nd storm in a record breaking year. However, statistics also indicate that even though tropical storms continue through to as late as December, this late-season weather usually is limited to affecting the Mexican coast and the Gulf of Mexico. The Eastern Caribbean and islands are usually storm free after September. But.... don't count on it. Mother Nature calls the shots, and there was Lenny in November 1999, coming out of the west, travelling east with little advance warning, and surprising and devastating many of the eastern Caribbean islands as it smacked into their usually-sheltered leeward coastlines.
So, with very close scrutiny of the weather, I headed back to Antigua and "Manx Mist" on Oct 16th.
2009 was fortunately one of the lightest years on record, with only 9 named storms, only 3 of which made hurricane strength, and the season was over for the eastern islands. Sigh of relief!
Then you're thinking about what might greet you when you open the boat up. A leak could have it filled with water. Damp could have it filled with mould. And then there's the possibility of invasions of insects or rodents. You take as many precautions as possible when you pack the boat away, and hope everything is looking good when you return. And it was. 2nd sigh of relief!

What is guaranteed to await you is - work.
The excellent folks at Jolly Harbour marina (Stephen and crew) had relocated MM to the work yard prior to my return.
After running through the check list of prepping the boat to return to the water, the only main job to do was the annual bottom paint job. So after a good sanding, and 2 coats of anti-fouling, Manx Mist was ready to go "splash".
One small nagging issue was around a leaky seacock on the engine water intake - it didn't appear to be a huge concern so, eager to be sailing again, I decided to ignore it - this would turn out to be an increasing problem for the rest of the season.
Anyway, back in the water on Oct 21st after 4 days of work in the yard, and we're ready to go sailing.
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