Weather Conditions: Wind 10 knots ENE. Clear Skies.

Leaving Great Harbour caused me the most apprehension I’d had about leaving an anchorage since St. Martin. I had gone through The Narrows and the Windward Pass (never a good labels to see on a chart), the Pillsbury Sound (I guess the rocks would be soft here) and Current Cut (another ominous sounding name) on a ferry from Road Town, Tortola to St. Thomas to get our visas extended (once again). The ferry ride confirmed my suspicion, the actual conditions were far more worrisome than the charts reflected.

So I spent the departure morning with the owner of one of the restaurants pouring over charts and talking about the most favorable routes. He wasn’t much help when it came to currents and wind directions (the items I was most concerned about); he basically ended up giving me the old worn-out Caribbean nonsense I’ve heard so much of in the last couple of years: “Just head on down this way, through these cays and then you’ll round these rocks here, then you got to squeeze through here, then you’re home free, it’s easy mon, but whatever you do, don’t follow the ferries because they end up on the rocks all the time.” Oh great, how encouraging to hear that pilots who navigate these waters daily “end up on the rocks all the time,” but I scarcely believed it. Thousands of boats navigate these waters every month without incident. We would just have to stay diligent.

After checking out of customs in Great Harbour, which by the way, was to date the worst customs experience we had in the Caribbean, we headed back to the boat to check on the crew and the progress they’d made to ready the boat for the voyage.

We’d weighed anchor by 11:00am, two hours after I had wanted to be off, and headed southwest toward the Windward Passage. The light wind and seas were pleasant, though our progress was slow, and by the time we made it between Lovango Cay and Durloe Cays (the actual Windward Passage) and approached The Brothers (two rocks sticking out in the middle of the Pillsbury Sound – the soft ones, I presumed), the wind backed off to 3 knots and the current was pushing us backward – exactly what I had feared.

As we fired up the engine and motored toward Cabrita Point, the entrance to Current Cut, the wind shifted out of the south-southeast (the Island effect I anticipated), and we shorten the sheets and beat through the narrow channel between the southeast corner of St. Thomas and Great St. James Island.

Just after exiting the cut, and breathing a sigh of relief, we turned west and continued motor sailing downwind to Charlotte Amalie when the transmission failed once again. So we turned of the engine and sailed the remaining way to our anchorage.

Fortuitously, we arrived after the last cruise ship had departed Long Bay so we sailed into the anchorage unmolested while putting more oil into the transmission. We started the engine and ran it just long enough to maneuver around the anchorage, drop the hook and get it set.