Jack Webb's cruising story is that of a bad night on the Bahamas Banks. An experienced singlehanding cruiser, he still learned several lessons.

Cruising Stories: Jack Webb | Drifter

Cruising Stories” are little glimpses of the cruising life. They’re not how-to’s or travelogues. They’re emotional and raw, hitting both the beauty of this life and its ugly side. Above all, they’re real.

Jack Webb is a singlehander aboard Drifter, a Westsail 32. Jack’s an experienced boater, but his night on the Bahama Banks is one that no amount of experience really prepares you for, other than simply making you realize that morning will come. Nights like this are rare — and the exact details will differ — but yes, they happen to everyone (Dave and I have had three that all resulted from being caught a lee shore in a squall).

I don’t repeat his story to scare new cruisers or those thinking about the life, but rather to point out that yes, there will be nights from hell. And we all learn lessons from them.

Jack originally posted his on his Facebook page and generously gave me permission to use it and his photos.


I left Great Harbour, in the Berry Islands at around 7:30 am on July 18, 2016, headed for North Rock on the north side of Bimini. That’s roughly a 70 nm run (a little over 80 statute mi), plus another 6-7 nm to get the Bimini Harbour entrance.

Winds were currently about 15 kt, almost dead behind me. I had a nice downwind sail, under mainsail alone, making between 4.5-5.0 kt (5-6 mph) in speed. I was anticipating a few squalls, with wind gusts to the mid-30s and possibly 40 kt. But with a little luck, I hoped to outmaneuver them. Sure enough, several squalls crossed my path. But rather than alter course, I simply trimmed sails to change my speed, letting them pass before me or behind me. Fortunately, I managed to miss them all.

My entire course on this route crosses The Great Bahama Bank, which is essentially a giant sandbar of varying depths, but typically quite shallow. As such, one can stop and anchor on the way across to get some sleep, before making the final run into Bimini. The GB Bank is seldom a very comfortable place to anchor. But as a solo sailor, it beats trying to make the entire 80 mile run non-stop.

The first half of my route crossed waters with depths ranging from 50-75’. When one considers that my crossing from Great Abaco to the southern Berry Islands took me through some depths over 15,000 ft (almost 3 miles), a mere 50-75’ is nothing. But anchoring where there’s a likelihood of squalls and high winds, requires the use of a prescribed 7:1 anchor scope. Anchoring in 50’ of depth would therefore require 350’ of chain and rope rode. Since this isn’t practical, I selected a waypoint near Bimini that was only 15’ in depth. By the time I reached that predetermined waypoint, it was about 10:30 at night.

While the winds were brisk, I rather unceremoniously came about to head into the wind, dropping my anchor and feeding out almost all my chain… but none of the nylon rode. Anchoring with a bowsprit requires a little thought, in order to prevent chafe. I’ve constructed a bridle that runs through the two hawse pipes in the port and starboard bulwarks, attaching the bridle to the chain with a Chain Grabber by ABI. This keeps the chain from rubbing against the bobstay. It also keeps the boat centered into the wind, to prevent it from yawing back and forth thereby reducing the strains on the ground tackle (anchor and chain) and completely removing strains on the bowsprit, anchor roller and windlass. My bridle works incredibly well with chain, but not rope rode. The rope rode is basically just there for backup and for extreme conditions. There are, of course, ways to make similar setups for rope rode. I’ve just never needed to use the nylon rode. (I think we’re getting there.)

The wind had picked up a bit and it was now blowing a solid 20 kt, with frequent gusts into the high 20s and low 30s. In addition, there were very steep rollers (long, undulating waves) hitting the boat. These caused the boat to hobby-horse relentlessly, as each grabbed the hull, easily tossing the bow up and down by 4-6’. Each time this happened, it jerked my chain (Actually, the anchor’s chain, not mine. On second thought… BOTH). This substantially reduces the likelihood of getting a good set on the anchor. Since there was such incredible force on the chain, however, it seemed that the anchor had properly set.

I headed back to the cabin to mark a waypoint on the chart plotter to indicate where the anchor had been deployed. Whenever I stop, and again when I set the anchor, I immediately mark a waypoint as a reference. This allows me to make sure that the anchor is well set and that I’m not drifting and dragging it. I had already marked the point once when I turned and headed into the wind — but before dropping the anchor — knowing that the boat would continued to drift until the anchor was set.

Now, I know set that waypoint… where did it go? Zoom out. Ahh, there it is… WAY back there.

My GPS indicated that I was still moving at about 1 kt (1.15 mph), which meant that I was indeed drifting. What a drag! A trip back to the bow indicated incredible forces on the chain, with no hint of dragging. I couldn’t have budged it, if I had to. (I know this, because I HAD to… and I couldn’t.)

But, having just deployed the anchor, I had not yet attached the bridle. This meant that all forces were being exerted directly on the windlass, anchor roller and bowsprit. But for some reason, the anchor chain was stretching out at a 90 degree angle to the hull, causing it to exert tremendous pressure against the wire bobstay, which an integral part of the running rigging that keeps the mast standing. Snap the bobstay and there’s a good chance, in these conditions, that the mast could be at risk.

I attached the bridle to the chain. Then, with all my strength, I released the chain from the windlass to give it enough slack that the bridle held the strain instead. Finally! Now I can get some rest. Sure.

When I got below, my chart plotter indicated I was still moving at almost 1 kt (1.15 mph). This wasn’t going to cut it. I was still out on The Bank, with no reefs nearby. But I would soon be drifting into somewhat deeper water, increasing the likelihood of dragging. At an increased speed, I could very easily drag onto the rocks, as I was headed in the general direction of some fringe reefs at the edge of the Great Bahama Bank. Back on deck.

I let out about 75’ of 100’ of the 1/2” nylon rode shackled to the end of my 5/16” high-tensile chain. In preparation, I had already attached it to the heavy cleat just inside the port side hawse pipe, knowing I would never be able to cleat it off while it was under strain.

Jack Webb's cruising story is that of a bad night on the Bahamas Banks. An experienced singlehanding cruiser, he still learned several lessons.


My biggest concern at this point, was the sharp 90 degree angle of the boat to the wind. Obviously, there was a tremendous tidal flow, exerting an even greater effect on the hull than the wind. Wind forces increase exponentially to wind speed. A doubling of wind speed increases the force on your boat (and ground tackle) four times. For example, a 20-knot wind typically exerts a force of 1.3 pounds per square foot; doubling the speed to 40 knots would quadruple the pressure to 5.2 pounds per square foot. Consider now, that the effect of the current on the hull is already exceeding the effect of the 20 kt wind to a point that I do can nothing to turn the boat back into the wind. Further, turned 90 degrees to the wind, the hull offers a very UN-streamlined 32’ of resistance to the wind, rather than a very streamlined 11’ of resistance.

To put this into perspective, think about when you were a kid riding in your family’s car with your hand out the window and your palm parallel with the ground, playing as though it was the wing of a plane. (Come on… you did that too.) As you rotated your wrist to make your palm perpendicular to the ground, it just about ripped your arm off. This illustrates the relative effect from the alignment to the wind. Your palm, however, remained the same size, while the surface area of my hull virtually triples from 11’ to 32’, when turned sideways. Add to this the effect of a 2-1/2 to 3 kt current against the keel, presenting another whole issue. OK… too much info.

The long and short of it is that I continued to drag across the bank. Due to increasing the scope of the anchor rode, I had now reduced the speed somewhat to 0.7 kt. To verify the rate of drift, I had started to mark a new waypoint every 15 minutes. At this point, my drift was a very constant 0.7 kt. And measured over a 1 hour period, I drifted 0.7 nm.

Clearly, this kid was not going to get any sleep tonight. I needed to regularly monitor the rate of drag to assure I did not unknowingly move into deeper water, thereby increasing the rate of drift to a point that the reefs waiting downwind would be reason for concern. I checked the distance to the point at which the water started getting deeper and calculated that at my current course of drift I should still be OK by first light.


It was now 3:10 am. I made another trip topside to check for possible chafe on the nylon rode, before going back inside to watch a movie to attempt to stay awake.

Jack Webb's cruising story is that of a bad night on the Bahamas Banks. An experienced singlehanding cruiser, he still learned several lessons.

Throughout this entire ordeal, I had left my foredeck light on at full brightness, so I could see what I was doing. In addition, I had my anchor light on, since I was [sort of] anchored, and also my stern light, since it lights my aft deck fairly well. From a distance I probably looked like an ocean liner (or at the very least, a landing strip). But as I looked upwind, toward the tightly stretched anchor rode, I saw an even bigger mass of lights… HEADED DIRECTLY TOWARD ME. I ran to the cockpit and grabbed my VHF mic and hailed the vessel. Fortunately, he answered the call. I informed him that I was the sailing vessel directly in front of him, certainly no more than 200 yards away. I asked if he saw me in his path. He answered, “Sure I do… now.” He changed his course and passed off my stern, missing me by no more than 50 yards! I have no idea how he could not have seen me in his path. He should have seen me with his Radar, or at least noticed the bright lights in front of him. But that would assume he was awake. My guess is that he had set the autopilot and went about doing something else… like napping. Had I not gone up on deck when I did, I would never have seen it coming, nor knew what happened when he hit me. Things like this really make one think.

What a night! Although the wind was blowing 18-20 kt with gusts to 25-30, this was NOT a squall… just the kind of constant and prevailing winds that makes a Westsail happy.

Although the anchor appeared to be set, I drug all night a a steady rate: 4-1/2 nautical miles over an 8hr period. I almost pulled up the anchor and head directly into the Gulf Stream. But I didn’t think I could even get it up, the way it was blowing, especially in the dark when it would have been virtually impossible to motor toward the anchor to reduce strain. Drifter’s bobbing like a rocking horse in the heavy swells did nothing to help the anchor’s hold.


Even in the daylight, it took me over an hour to get the anchor up, with a 2-3 kt current and the resulting 90 degrees alignment to a 20 kt wind. I was pulling up the last 20-30 feet of chain (which I could tell by my markers), when it suddenly felt as I though my full strength had returned, despite a long and arduous night. Drifter is still bucking like a bronco with each ensuing swell. So, rather than stress the windlass, I retrieved the chain by hand, using the downward roll to pull in the slack, then locking it against the anchor roller to prevent losing my progress on the upward roll. The last 20′ came up much easier, and I could feel it give. I assumed it pulled out of the sand. Or, did it? The last few feet (in this case 20’), it always feels lighter, because you are only pulling up the weight of the anchor and chain… not the bottom of the ocean. With only 20’ to go, I would only be retrieving 70 lbs: a 45 pound anchor plus 25 pounds of chain (5/16” chain weighs 116 pounds per 100’).

But I felt it getting easier almost instantly. When it finally came to the surface, I couldn’t believe my eyes. My very expensive, highly respected, Made-in-Scotland, 45 lb CQR had turned into a 10 lb OMG.

Jack Webb's cruising story is that of a bad night on the Bahamas Banks. An experienced singlehanding cruiser, he still learned several lessons.

Jack Webb's cruising story is that of a bad night on the Bahamas Banks. An experienced singlehanding cruiser, he still learned several lessons.


• I have a 48 mile Radar installed, but I never use it at anchor, due to the electrical drain. I may well have to change that policy.

• I have not yet installed AIS (Automatic Identification System), but was planning to do this in the fall, before heading back to the Exumas. Previously, I would have installed a receiver only, allowing me to identify commercial vessels (that are now required to transmit). I’m now thinking it would be smart to install an “AIS Transponder”, that will allow me to both transmit and& receive. (More electrical drain.)

• Although I was not in a conventional “shipping lane”, I was nonetheless reasonably close to a “recommended route” across the bank. I was a little south of the route, in order to anchor in shallower water. But over the course of the night I drifted back toward that route, beyond my control. Next time, I’ll pick a place a little further from the beaten path.

• I have never witnessed that much current on the Bank. Presumably it was due to my close proximity to Bimini Island. If I ever need to anchor in that proximity again, I will do so a few miles further east. Better yet, the next time I’ll do the first half of the trip over the evening hours, so that it’s already daylight as I approach Bimini (or Cat Cay, if on the southern route).

• I’m totally baffled by the fact that my anchor seemed to be set, based on the forces exerted. Yet I very steadily continued to drag it… and then snap like a match stick as I tried to bring it up. It almost makes me wonder if perhaps I had indeed set the anchor, but onto a sunken vessel of some sort, which I then drug across the bottom at a constant rate.

Actually, the more I think about this, the more plausible it sounds. There must be countless small fishing boats sunk in this area. I believe the bottom here is probably hard limestone, with a relatively thin layer of sand. Hooking a small sunken jon boat or something similar, could permit me to drag it across that kind of bottom at a reasonably steady rate. At the same time, it could account for the fact that the anchor continued to hold, albeit in motion. The overall weight of the snatched vessel, etc, could also account for my inability to free the anchor, once I had positioned Drifter directly over it. The CQR plow anchor is designed such that lifting it from directly above should easily free it, no matter how well it is set. But the continual bobbing of the bow in the swells could possibly have exerted enough stress, at the wrong angle, to cause the shank to snap.

Jack Webb's cruising story is that of a bad night on the Bahamas Banks. An experienced singlehanding cruiser, he still learned several lessons.

  • Anonymous
    Posted at 07 February 2018 Reply

    Wow, Jack’s story makes my uncomfortable night on the Berry Banks sound just whiney. Thank you Carolyn Shearlock for publishing and thank you Jack Webb for sharing.

  • Anonymous
    Posted at 07 February 2018 Reply

    Whoa I’m exhausted just from the read. Great job Jack and my hat off to you for your fortitude.(as if you had a choice)

  • B. Davis
    Posted at 08 February 2018 Reply

    That picture of a broken 50 pound anchor is absolutely incredible! It must have taken several thousands pounds of force to snap that big boy:). Also, after sailing all day until 10:30pm, you were obviously very tired, and had the discipline to not take 20 minute to an hour nap, or we all may have not heard this amazing story that was much more interesting than any adventure.
    Cheers Jack, glad you are still with us!

  • Sarah Penossi
    Posted at 12 February 2018 Reply

    Jack what a wonderful article, and thanks for sharing. You must pack a lot of coffee for those long nights without sleep:) Also, I really liked that you added those definitions to many of the lesser known parts and sailing terms.

  • Jack Webb
    Posted at 13 February 2018 Reply

    Thanks all, for the nice comments. And thank you, Sarah, for noticing the “info links”. I have a varied list of followers on my Facebook page. Many are seasoned sailors… others but lowly landlubbers. It’s a challenge to write something that will hold the interest of both. The links were the best way I could think of to portray the event in a manor that those who were unfamiliar with nautical terminology could easily understand its meaning, without boring those who expect to see it. I appreciate that you noticed.

    As for the long nights, I’m fairly used to them. I don’t recall the movies I watched that evening, but I know I must have enjoyed them immensely. It would have been hard to sleep, knowing I was dragging at 7/10 of nautical mile each hour anyway, even though I was well away from any reefs.

    In retrospect, I’ve decided that I had actually been dragging only the chain and anchor shank all night. I suspect that the anchor caught on a ledge in the limestone bottom, as I was pitching up and down while first setting the anchor, snapping it with one of the thrusts of the steep waves… right at the very beginning. With the weight of several hundred pounds of chain and being pushed by the heavy winds and current, it was just difficult to tell that the anchor had never actually set.

    Another lesson learned.

    Jack Webb,

  • Cyndy
    Posted at 13 February 2018 Reply

    As a sailor, I appreciate the correct terminology. As a captain with a noob aboard, I appreciate not having to explain it! Great article and one of the reasons I’m not a singlehander. I’m impressed that the bowsprit held with the forces that would break the shank on the CQR. If you talk to Carolyn about it I bet she talks you into a Mantus!
    Going to follow your blog when I have wifi. Thanks for a great salty tale. I dealt with some currents and I’ve always wondered about the math… Thanks.

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