We left St. Thomas for Ile A Vache at 1:00pm after lunch at the fuel dock with our friends, Tom and Christie from s/v Ashlana. The wind was blowing out of the Southeast at 14 to 17 knots as we left Long Bay under a full main and the staysail. As we left the protection of Muhlenfel’s Point, we started rolling in the four-foot seas and everyone went below until their respective watches started.

5/11/08 Sunday

At sunrise the wind was unchanged and the night had gone by without any notable events. Two very large, light gray porpoises came to visit at 9:30am; they were longer than our fourteen-foot dinghy. Thirty minutes later, we were visited by a pod of 30 small porpoise. At 10:45am, after breakfast, we raised the mizzen and standing jib. The boat totally leveled out (not rolling from port to starboard) and we more than doubled our speed. By 11:12 a.m. everyone was up and feeling better and at 1:00pm, 24 hours later, we had gone 61.5 miles. The wind had been dropping all afternoon, and when I took my watch from Alexis at midnight, it was horrible. There was little to no wind and we rolled in the windless swell with the rigging banging and squeaking into the early morning hours.

5/12/08 Monday

By midmorning the wind had picked up again and at 1:00pm, we had traveled 97 miles in the past twenty-four hours. At 1:30pm the wind had picked up to 20 knots with a building swell as well. I took Tracy’s watch that afternoon, and toward the end of Preston’s watch (8:00pm), we reefed the main two points. The wind blew all night up to 20 knots. During my watch a flying fish hit the back of the settee and flopped on the deck for a while. Then about an hour later, another hit a pole holding up the hardtop and sent a shower of scales over me. Had the pole not been there, it would have hit me, and by the sound of it whacking the pole, a direct hit would have hurt a lot. I turned off the overhead light over the CD player that apparently had been attracting them onto the boat.

5/13/08 Tuesday

The wind had slowly been shifting to the east, which pushed us further south, and by 1:00pm, we had traveled 118 miles in the past 24 hours. We jibed to take advantage of the easterlies and to make a more northwesterly course. As the afternoon wore on, the wind decreased and by sunset we started to roll heavily, which continued throughout the night.

5/14/08 Wednesday

By sunrise, the wind was holding at eight knots and we were still rolling heavily from side to side, and by 9:45am we had made 92 miles but were now virtually at a standstill in a dead calm. We kept the sails up for awhile, hoping for wind, though they were taking a beating, and by 11:00am we gave up and brought down all but the staysail. I then sent my first email via the SSB radio to my mom to tell her we weren’t going to be making it to Ile a Vache today. That afternoon we tried to “heave to” but the boat just sailed to windward at one knot so we left the wheel lashed down and took single two-hour ship watches all night as the boat heaved relentlessly in the four-foot swell.

5/15/08 Thursday

By sunrise, the winds increased to between 5 and 7 knots and by 10:00 they were up to 11 to 13. We raised the sails and started off once again toward Ile a Vache. It ended up being a beautiful afternoon to sail — clear skies and consistent medium wind. At 12:00 noon I checked the bilge, and by 1:00pm we had traveled 13 miles in the last twenty-four hours. At 1:30pm I turned on generator and had it back off by 4:30pm. The wind had been steadily increasing all afternoon, and just as the sun had gone down, we noticed lightening off our starboard side over the Dominican Republic. On Lauren’s watch, Alexis woke me at 11:30pm to tell me the wind was gusting to 20 knots and the squalls were increasing and getting closer. I took over at midnight and had a white-knuckle ride in the consistent 25-knot wind until I couldn’t take it anymore and woke Preston and Lauren at 1:40am to reef the main, drop the standing jib and the mizzen.

5/16/08 Friday

At 10:00am the following morning we jibed again and took a heading toward 330 degrees, 200 miles to go for Ile a Vache – maybe 2 days away depending on the wind. It was currently blowing at 16-18 knots and the seas were rough from the night of high wind. By 1:00pm we had traveled 135 miles in the last twenty-four hours. As the evening wore on, the wind slowly fell off. I slept like a rock from 4pm to 12am. During my watch at (12:00am – 4:00am) it was blowing 10 to 13 knots and the seas were abating. At 2:00am I woke Preston and Tracy (for her watch) to shake out the double reef in the main and hoist the standing jib though we could clearly see thunderstorms pounding the landmass of Dominican Republic.

5/17/08 Saturday

As the sun rose we could barely make out Isla Beata off the southern-most point of Dominican Republic. By 1:00pm, we had traveled 92 miles in 24 hours. We had 108 miles left to go to Ile a Vache. We turned on the generator at 1:45pm. Two tankers passed between the island and us, and we were visited by two dolphins today. We sailed through a huge flock of feeding seabirds and threw out a lure, but to no avail. The wind clocked its way back out of the south-southeast at 11 to 15 knots causing us to steer in a more northerly track than we wanted to go so we jibed, turning more toward a west-southwest track over our rhumb line. The wind fell off to under ten knots after dark and we rolled once again all night.

5/18/08 Sunday

By morning the wind had increased to 15 knots and we were back under way in mild seas. All day the large mountain range of the southern peninsula of Haiti loomed on the horizon, and a co

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.