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.

We headed out of Nanny Cay Marina after a morning of anxiously re-installing the transmission’s heat exchanger (it blew an o-ring the night before) and testing all the other engine-related systems. As we motored through the narrow inlet bordered by the jetties that were so menacing just weeks before upon our crippled entry, and rounded the southern coast of Tortola in the benevolent ten-knot breeze, I put the most apprehensive crew at the helm, Tracy. I’m not sure why she was so tentative about piloting her home, but I pretty much had to order her to take the wheel, “and smile when you do it!” Besides, the seas were incredibly calm in the western end of the Sir Francis Drake Channel, and I thought it might be a long time since we saw sailing conditions so perfect.

As we approached the western end of Tortola and entered the pass between the Thatch Islands and Soper’s Hole, I took the wheel to weave our way in very light wind (in the lee of the island) north through the narrow pass and all the bottle-necked boat traffic going in every direction. But once we made it through the pass, we were unpleasantly surprised by 15 to 20 knots of northeast wind, the resulting seas and menacing clouds on the horizon. It was like a completely different day; definitely the “island effect” in full force. For the first time on Kai Ohana, we would be beating the rest of the way to Jost Van Dyke.

So I cheated. I fired up the engine, putting it through its first real test since the transmission refit, and we motor-sailed the five miles (about an hour) to our destination. But by the time we got to Great Harbour, she was overheating and we had to drop the anchor quick. As with pretty much every anchorage in the Virgins, the bay was full of boats so we had to anchor further out than any of the others in about thirty feet of water. Because of the northeast wind, the anchorage was surprisingly calm though it seemed very exposed to the Atlantic Ocean – any southeast blow would make the bay untenable at best.

As soon as the engine cooled down, we discovered the overheating problem was caused by an empty antifreeze reservoir because a hose had been reinstalled improperly, which produced a loop or air gap in the system giving the impression there was more fluid in the system than actually existed. The sensitivity, complexity and intricacy of the systems on a boat still amaze and befuddle me. It’s true what Tania Abei told one of the kids in an email: “Your learning curve is going to be steep for quite awhile.” It will be nice once this hill I’ve been peddling up for the last two years starts to level out.

We rounded the northern side of Marina Cay under motor and raised the only two working sails we had rigged at the time (the main and the staysail) and progressed down the south eastern shore of Tortola at three knots in very calm seas. My mom and Cole enjoyed the trip very much, but the slight rolling motion eventually sent my drowsy mother to my “sea bunk” about half way through the voyage for what appeared to be a very serene nap. It took a couple of hours longer to arrive at our destination than I had anticipated so we overshot our ETA in Nanny Cay Marina by about an hour and a half. I radioed the marina and told them of our schedule and turned on the “Iron Wind” (the engine – something I don’t like to do very often, diesel being over $5 a gallon in the Caribbean) to get there before the crew went home.

But when we arrived just outside the breakwater (as we were taking down the sails and being blown into the jetties) our hydraulic transmission just stopped working. In a state of “high anxiety,” I woke up all the snoozers on board and ordered Sara and Alexis to the windlass to drop the anchor on my command, and then I pulled the floors in the salon and dove into the engine room. After checking the oil level in the transmission, I discovered that had it not only lost all its contents into the bilge, but we also confirmed that we indeed had lost all ability to maneuver. I quickly poured (an oxymoron) more oil into the transmission (so it could eventually all end up in the bilge as well), and we were able to limp into the harbor only to find a German-registered sailboat spinning around in the basin trying to back into the lift.

Though we were late and I officially lost my “slot,” I got on the radio and called the dock master and told him that not only were we dragging the bottom of his tiny harbor, but we were at risk of losing our maneuverability and he needed to get that boat out of the basin if he didn’t want me to “rake the harbor.” The very professional dockhands calmly instructed the captain of this errant vessel to tie off to a nearby dock and let me into the travel lift slip. Preston, in the dinghy, acted as my bow thruster and maneuvered the bow as I eased her into the travel lift’s slip stern first, and just as our lines were caught by the hands waiting on the docks, the transmission sputtered into permanent neutral.

On the day we planned to leave, April 3, 2008, we woke to cloudy skies and gusty northeast trade winds. Sailing across the Francis Drake Channel in these conditions would have been effortless, but gracefully anchoring in a potentially crowded anchorage could pose some problems in adverse conditions, and I had no idea what to expect at our destination.

We prepared the boat for the sail to Trellis Bay and by noon we were hit by a 25-knot squall that lasted about an hour and a half. The wind clocked all the way around the compass toward the tail end of the squall, which resulted in the twisting of our two anchor chains (we set two hooks out anticipating the same wind we had in St. Martin), so when the squall stopped and the wind completely died, Preston had to dive the anchors to untangle them.

As we got the anchors in and the sails raised (about 3:00pm), the wind was so light that it did no good in pulling us away from being drawn by a current into the other boats at the anchorage, so we started the engine and pushed our way west out of the lee of Virgin Gorda. Once around the point, we picked up a light north breeze and slowly made our way across the channel. As we progressed, the wind increased to 12 knots out of the northeast, which put us at the mouth of Trellis Bay just before sunset.

Our exposure to the charter boat community in Spanish Town did not prepare us for what we were about to experience on the other side of the channel. Certainly The Baths (just south of Spanish Town) are a huge tourist draw, but the lack of “good” anchorages near them makes it more of a ferry destination than a charter boat destination. It’s true we had a few charter boats pull up beside us and tie off to the mooring balls, but due to the southern exposure of the anchorage and the few days of rolling that we experienced (though nothing near what we had lived through in Marigot Bay) there were often days where the moorings sat empty.

Not so in Trellis Bay. When we rounded the northeast point of Tortola, there was literally a wall of hulls against the yellow buoys (the airport southwest of the bay prohibits anchoring outside the yellow buoys – for some reason they don’t like masts in their take-off zone) blocking all access inside the bay. As we approached the line of boats looking for the smallest of openings we could squeeze our 50 ton vessel through, we were greeted with many cruisers on their decks with hands on there hips and shaking there heads in a, don’t-even-think-about-it sort of posture. We turned around and headed north to Marina Cay where our luck was not to change for the better; it was packed as well. We tucked up in behind the edge of the reef as close as possible, but the 15 to 20 knot wind and the resulting chop coming out of the southeast was barely thwarted. Also the fact that we had anchored upwind of two boats whose combined value exceeded $10 million prompted me to issue an all night anchor vigil.

Preston and Alexis took first watch while I pretended to sleep (I just knew I was going to hear those dreaded words, “We’re dragging!”), then Lauren and Sara took the watch until 2:00am (while I continued to pretend to sleep), then I took over until 8:00 the next morning, at which point an unexpected mass exodus of the charter fleet had begun, the two private yachts behind us being the first to leave.

The way the mooring balls work is the white ones are pretty much for the charter fleet (though anyone can use them) on a first come, first serve basis and cost around $15 per night. Unfortunately for us, they only accommodate boats that are a maximum length of forty feet (about half the size of us). Any colored balls are reserved for commercial use, owned by others, or reserved for dive boats. I had my eye on a big orange ball right up in the crook of the reef near the fuel dock, and luckily enough, a huge privately-owned catamaran untied itself and departed with the rest of the fleet. I asked Lauren to jump into the dinghy with Preston and ask the guys at the pump for permission for us to tie off (we’ve learned long ago, never send a man to ask another man for a favor, when there is a woman there who can do the job so much better). The guy at the pump’s response was more than gracious, “Yo beautiful boat would be da perfect fit tied off to dat der mooring, mon.” It ended up that it was the private, yet un-used, mooring ball of the guy who owns the island (and Pusser’s Rum), Charles Tobias, and ours for nearly two weeks for a mere $15 a night.

We decide to run for Virgin Gorda anyway. On the morning of February 25, 2008, we weighed anchor in the lagoon and followed a number of boats into the channel from Simpson Bay (on the Dutch side of the lagoon) to the Marigot drawbridge for the 8:15 opening. The tide was slightly less than half way out and I was concerned with our 7-foot draft (we’ve only just made it through the channel at high tide). We grounded in the north part of the channel, but accelerated to the point of digging our way through. A 90-foot luxury yacht behind us grounded where we did and missed the bridge opening.

We sat on the hook in Marigot Bay in nearly dead calm all day (something we were very much enjoying) and prepared the boat for the passage. At 9:00pm we were blessed with a final farewell from our Czech friends Martin and Romana, and by 10:00PM, we had the anchor weighed, sails hoisted and were on our way west toward the southern tip of Anguilla.

By 11:00PM, we were traveling at 1-2 knots in 5 to 8 knots of wind and I took to my bunk for some shut-eye. Sara and Alexis had taken turns steering all night (I woke every hour to check on them), and I took the helm just before sunrise (5:00AM). Since we had worked our way out of the lee of St. Martin, they had both grown increasingly sick, and by the time I took the helm, they were ready for bed.

We had just gotten around the southern tip of Anguilla (nine miles in seven hours) when the first squall hit. The wind went from five knots to 20 knots in an instant then calmed to slacked off to 15 to 18 knots thereafter. By 9:00AM, we had picked up a few miles, but we appeared to be on a collision course with a freighter (we were heading west/southwest, they were heading northwest). With one eye on the growing freighter to our south and one eye on a growing squall to our north, I feared the worst, but the 25 knot wind from the approaching squall left me no choice but to veer north west (into the wind to relieve the sails), which allowed the freighter to pass with plenty of room to spare. Forty minutes later, we were back to 15 to 18 knots of wind and skating toward the Virgins.

Against Preston’s advice I decided to drag the dingy behind us, but it was becoming very apparent that I had made a grave error in judgment. The dinghy was really banging around in the swell behind us, and I knew the weather was only going to get worse over the next 24 hours — how long it would take us to get into the lee of Virgin Gorda. But on we sailed in the growing wind and swell and prayed for the best because there would be no way we could have gotten that dinghy on board in those seas, not without tearing something (or many things) up in the process.

Preston came up to keep me company at 9:00AM, but he didn’t look too good. Lauren came up shortly thereafter, and she didn’t look so hot either. I on the other hand felt miraculously well. I have been very prone to seasickness in the past, but I had been spared of it so far. For the next several hours we took turns steering and sleeping in the settee. The wind had built to 18 to 22 knots and I actually thought at the rate we were going, we might make it to Ginger Island Pass by sunset, especially if we used the engine. So we fired her up, picking up a few more knots and watched the chart plotter for an hour.

It was evident that if we made it to the pass by sunset, we wouldn’t have enough time to anchor in front of Spanish Town in twilight so we turned the boat up into the wind and reefed the sails down in 25+ knot gusts dipping the bowsprit every few waves and nearly capsizing the dinghy. I came as close to getting sick here as I did the whole trip.

We shut the engine off and calculated on the chart plotter the downwind tacking strategy we’d have to take to slow us down enough to get us into the pass by sunrise. I was exhausted, though I’d recovered from the reefing experience, and I tried to get some sleep on one of the settee benches while the boat pitched and yawed, waking up every so often to check and re-check my calculations, inspect the rigging (at some point in the chaos, we accidentally jibed which broke the port fore spreader off — it was hanging on by the spreader light wiring and beating the rigging aloft) and look with dread at my still-attached, but badly abused dinghy.

Lauren and Preston took turns at the helm while I dozed, but by sunset, they had both gone under for some sleep in their own bunks. It was lonely at the helm by myself, but there was no time to dwell on it. The seas were tall, very steep and close together — as the bow would come off the back of a swell the stern would immediately lift with the oncoming one. The boat never found a rhythm and had to be constantly corrected for fear of accidentally jibing again. And the dinghy would surf down the oncoming wave, sometimes plowing into the stern of the boat and then jerk on the slacked painter as Kai Ohana would pull away. It was waking a nightmare. By 9:00PM, I had resigned myself to the fact that we would probably be replacing the dinghy in the Virgin Islands.

The wind had relaxed at sunset to 16-18 knots, but after it got dark, it was back up over twenty and didn’t let up until sunrise. By 10:00 I was literally hallucinating. The compass, right in front of my face, with its red glow was starting to take on a life of its own. It looked like a face in my blurred vision and as it bobbed in its fluid, it looked as though the face were trying to say something. Just before I had gotten immersed in a conversation with this newly animated object, Lauren had come up to check on me. “God, I hope you’ve come up to relieve me because this compass is trying to talk to me!” I confessed. “Yeah, I can relieve you,” she replied, “but I don’t want to hear about any faces in the compass.”

I laid on my stomach in the settee on a couple of pillows, gripping the edge of the bench for fear of sliding forward or backward off the bench, and slept in fits and starts, raising up occasionally to look at or discuss the proximity and course of nearby boats. Lauren, bless her soul, took the helm until 2:00AM, which provided me enough rest to get me through the early morning shift with a somewhat clear head. By sunrise, the lights on dark horizon faded into the profile of the islands and the wind had dropped to 8 to 12 knots. We should have shaken out the reefs, but Preston was still down below and I couldn’t bear the thought of pointing back into the wind, slamming the bow into the oncoming swell and un-reefing the sails. So I watched as one boat after another raced into the Ginger Island Pass while we crawled.

Eventually we made it into the Francis Drake Channel and in the lee of Fallen Jerusalem, we motor-sailed north (in the northeast trades) in a “mill pond” toward Spanish Town. As the motion of the boat slowly abated, its hibernating inhabitants started to come to life — first one, then another, and another, crawling out of their cabins rubbing their faces and trying to see through the sleep (and who knows what else) that sealed their eyelids. By 8:00am, we dropped the sails and then the hook in 30 feet of water off Spanish Town, Virgin Gorda.