There is plenty of upwind sailing getting to the Caribbean and going east on your way through the islands. The never ceasing eastern trade winds are relentless day and night through December, January and February. I am told it will calm down in March and April but I haven't seen it yet.
When we were at Green Island Antigua the wind blew at between 20-25 knots from the ENE 24 hours a day for 14 days in a row. The never ending upwind sailing is tough even on a fast upwind boat. We love upwind sailing back home, much more than going downwind. We have a boat that is very fast upwind especially in heavier weather. After 5000 miles it seems as though 4000 of it has been with an apparent wind angle of 50 degrees or less.
A 135 LP headsail is too large considering the amount of upwind sailing. We nearly always go out with a triple reefed main which on our boat (a headsail driven boat) is the best configuration as it allows us to sail with a less furled, more efficient headsail. For our next trip we will either carry a 100 LP headsail on the headstay instead of the current 135 LP or more likely will add a smaller roller furled sail to our inner forestay. Today we carry a storm jib on the inner forestay as a sail for really heavy conditions. When we convert to a furler on the inner stay the sail will be small enough that it will be a reasonable sized storm jib when partially furled.
Terri complains about rough ocean sailing too much, I need to find a new wife. This comment was provided by Terri :)
Jon
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