Bahamas, Part 2

Day 1: Key Biscayne to Bimini, 56 nm


Day 1 route

The Gulf Stream crossing is uneventful.  We depart Key Biscayne at 7AM, are in the ocean at 8AM, and are anchored in Bimini at around 4PM on January 31st, 2007.  The light northeasterly actually helps us because we can surf down the remains of the north swell, but it's too light to cause "elephants" in the Stream.  We motor the entire way, at around 6 knots and 2/3 throttle, and use about 6 gallons of gas.  Aside from some troubles checking in with customs (No boat registration!  It's not in the bin where it's supposed to be!  And the boat is supposed to be at one of the marinas, not the anchorage, so that Customs can examine it if they want to.  Seems like the kind of thing you would mention in a cruising guide, no?)  Fortunately, I have brought along the survey, whose raised notarized seal works for the customs agent.  I happily lower the quarantine flag and raise the Bahamian courtesy flag for the first time.

It sure would have been nice to have an autopilot, though.  I steered about 70% of the time, and Tanya 30%, and it's really boring, particularly under power.  At least there's no constant pressure on the tiller like there is with the Avalon, because the inboard engine's shaft is offset from centerline.  Another nice thing about an outboard is that you can turn it slightly to counter the force from the prop's rotation, plus it has a trim tab.  And an outboard can be a lot more efficient than an inboard because it can use a fairly big 3-bladed prop that would kill your sailing performance if you left it in the water.  Most inboard sailboats use small 2-blade props that spin like eggbeaters but don't move you too well, or folding props that tend to fail and cost at least $1000, but you tilt up or retract an outboard when you're not using it, so it's not creating drag.

We move the boat from the anchorage to one of the cheap marinas.  At 90 cents a foot, you have to be pretty stingy to anchor out.  We did see a guy from Erie PA anchored in a MacGregor 26.  I guess if you're willing to sail a Mac 26 across the Gulf Stream you can do whatever you want. 

We have dinner at the Red Lion.  Bimini is kind of seedy, dusty, and dilapidated, and it seems that half of the several hundred residents spend most of their time cruising up and down the single paved 2-lane road with few sequential yards of sidewalk.  But they are very friendly and accomodating, apparently genuinely, not in a "Let's sucker the tourists" way.  (Note: after staying in Cat Cay on the return, I would recommend it over Bimini, if only because it has wifi, great showers, and a decent bar/cafe.  Also they don't treat non-members as second-class citizens like they do at Chub Cay.)  If you want to see real life in the Bahamas, go to Bimini.  A middle alternative would be the Big Game Resort at Bimini, which is somewhat exotic by Bimini standards but still nothing compared to the private airstrips and clubhouses of Chub and Cat Cays.  We visited Big Game to see if we could use the wifi, but it wasn't working.


Day 2: Bimini to Mackie Shoal, 60 nm

Day 2 route

On day 2, we experience the good and the bad, and begin the litany of mistakes.  Mistake 1: we get a late start because I have some work things to finish up.  Mistake 2: we have an old weather forecast and no way to obtain a new one, and we're too impatient to wait around for an hour to get on the single Internet terminal in the Batelco office.  Next trip we will definitely have a decent SSB receiver to get weather forecasts.  I might pick up the new Grundig because it's a lot cheaper than the ICOM receiver, but it would be frustrating to get to the middle of  nowhere and find that it doesn't get any real SSB reception.  Apparently an SSB needs a honking big antenna and "ground plane", but I'm not sure if that's just for transmission.  (Update: just found a site that describes how to use a cheap SSB receiver to get Weatherfax.  Wish I had known about it earlier!)

We go for a swim anchored on a beach off Bimini, and I take some pictures of the boat from the water with my new waterproof camera.  I'm hoping to get that classic half-submerged-lens shot, but I realize it's much easier with a lens that's 2" in diameter than one that's 1/2".

The next mistake was in underestimating the distances involved, or at least the times it would take to cover distances.  The trip across the Gulf Stream was fine after a couple of false starts.  That's around 56 miles.  But the second day, from Bimini to Chub Cay, was problematic.  You cross the Great Bahama Bank on this leg, and it's a total of 90 miles.  The cruising guide says you can anchor in the bank since it's rarely more than 20 feet deep.  It's like a giant shallow lake.  I figured we would get part of the way across, anchor, and continue the next day.

Now that we're back home and I have 20-20 hindsight I realize why most sailors choose to depart Miami at night: they get to Bimini at the crack of dawn, check in, and just keep going.  Or they just check in at the next landfall.  Another thing the cruising guides all failed to mention is that you can pretty much sail as far as you like without checking in as long as you're flying the yellow quarantine flag, which implies that you're going to check in as soon as possible.  I guess it's the kind of information that's taken for granted among experienced cruisers, but aren't you buying a cruising guide to make up for your inexperience?  If we had left first thing in the morning we would have gotten to Chub Cay without any problems.

After rounding North Rocks, we really ripped across the first part of the bank.  That's where I took the video; we hit 14 knots a couple of times, towing the dinghy, and on a close reach to close hauled but never at the point where we really had to pay attention to the telltales to make sure we weren't pinching.  I can't wait to get into conditions where I can study the upwind VMG of the boat.  The prevailing opinion of those who know how to sail these boats is that you avoid pinching at all costs.  Monohulls typically have a lot more forgiveness about pinching because they have ballast which gives them momentum.  Plus they're not moving that fast anyway.  On my boat there's no difference in apparent wind between close reaching and close hauled.  The wind is as far forward as it gets in either case.  The only difference is in which way you're pointing relative to the true wind direction.

At one point I looked back and the old Sears Gamefisher outboard was no longer on the dinghy.  I didn't care so much about not having an outboard because we didn't plan on any long dinghy journeys, but I would have felt terrible if I had dumped a gallon of gas into this pure water.  Plus the engine was a family heirloom and ran amazingly well for a 30-year-old motor.  So we slowed down and dragged the dinghy in, and discovered that the engine had bounced off its mount on the transom and actually landed in the boat.  Note to self: do not tow dinghy with outboard attached. 

The cruising guide says it's a bad idea to sail on the bank at night because there are shallows and shoals.  I realize now that the author is extremely conservative, and basing his recommendation on his experience in a monohull.  The bank never got shallower than 10 feet, which is about 5 feet more than we need to sail, even with the board down.  A few times the knotmeter's reading started going up over twelve while the depth was going down towards twelve, and I thought they might converge.  That's when I was going to slow down.  It would be different if it were an area of coral heads, but the only danger was shallows and gradual shoals, so we would have had plenty of warning.  It's also not a bad idea to pull the board all the way up and just sail with more leeway.  It wouldn't have mattered much on a close reaching course anyway.  I have found since the trip that the Bolduc's web site on "microcruising" has a lot more relevant information than any cruising guide, because a multihull behaves like a big dinghy most of the time.  For instance, with the daggerboard and rudder up, we can motor in 18" of water.  If and when I build the daggerboard rudder, in theory I'll be able to sail in 18" of water as well.
Bill at helm on Great Bahama Bank
At the helm on the Great Bahama Bank

Tanya on the Bank
Tanya at the Bank


We stopped sailing at dusk, and the wind was still rising.  Having just launched the boat a few months before, I was not comfortable sailing at night.  Sometimes I recall the crazy things we used to do with the Avalon in San Francisco, like hopping aboard at 10PM and sailing for a few hours in the Bay, but that was a different time, place, and boat, and we knew the local landmarks and conditions so well that we could almost as easily sailed with our eyes closed as open. 

I figured we should continue for a while because it was only 6PM.  So Tanya had a sunshower with water I heated on the stove and we motored another 4 hours and then anchored, which was my fourth mistake.  It was like trying to sleep in a washing machine.  The wind kicked up a short chop on the shallow water and neither of us got much rest.  We should have just kept motoring.  Later in Chub Cay I met a guy on a 50-odd foot Bayliner (powerboat) who said he was midway across the Bank at the same time we were when he heard the weather forecast, and he put the throttle down, hit 22 knots, and burned $1000 of fuel to get to Chub Cay before things got worse.

Day 3: Mackie Shoal to Chub Cay, 32 nm

Day 3 route

The next morning, the wind had gone around to ESE, and the trimaran is really bad at motoring into the wind.  It's just too light to have any momentum, so it's stopped in its tracks every time it gets hit with a big wave.  It also has a lot of surface area, and therefore wind resistance, compared to a monohull.  We didn't want to sail because we were approaching the convergence of shoals to the north and coral to the south, at the entrance to the Tongue of the Ocean.  You can see all this in the route picture above, about midway between waypoints BANCH and CHUBCY.  The first islands of the Berries appear to the north of the track, and the line of coral heads that stretches north from Andros are just south of the track.  The pale water is shallow, and the deep blue is the Tongue, which is technically part of the Atlantic Ocean, so those swells have a long way to go and to grow before they get to the shallows.  We would have had to make shorter and shorter tacks to get through the opening between the Banks and the Tongue, in 20+ knots of wind.  Worse, we would not really have known when we had to tack because the obstructions we would be trying to avoid were underwater.  But motoring we were making 3 knots at best, even with a following current.  (This was the only point in the entire trip where we really needed tide/current tables, which fortunately were in the back of our cruising guide.  Even the supposedly killer rips between the islands of the Exumas were nothing compared to what I was used to in San Francisco.)  Fortunately high tide was around 7AM so we had a decent current pushing us into the ocean.  Unfortunately, current against wind makes for steep chop.  The swell, which came directly off the Atlantic ocean, was short and steep because the depths went from several thousand feet a dozen miles away to less than 15 feet in the Bank.  The prop was out of the water about every 20 seconds and once a minute we would slam a wave so hard it would stop us dead.  It would take most of the day to cover the 32 miles to Chub Cay.

My next mistake was to raise the sails in 25 knots of wind because we were using a lot of gas (we had to keep the engine at full throttle to make any progress) and I thought we might run out and get blown back into the Bank.  We started with around 12 gallons but were on our last tank.  I raised the main but I hadn't figured out the reefing system exactly and when I tried to roller reef the end of the boom was pretty much in the cockpit.  So I raised it all the way.  This was OK (we were cranking along at 9 knots and the waves weren't nearly as much of a problem) until the carbon fiber bracket holding the mainsheet cam cleat started to slowly break. 

I eased the main but when I had raised it all the way I hadn't gotten all of the slugs into the track (mistake number what?  I've lost count.)  So with the main eased and luffing a bit it was just a matter of time until a gust hit the baggy bottom of the sail and ripped the slugs out like ripping the buttons off a shirt.  My worst moment was trying to get the 400-square foot mainsail under control when it was only attached at 3 points and flogging like mad.  It actually smacked my glasses off my face but Tanya, amazingly, caught them as they flew through the cockpit.  We lost a batten which she tried to recover, and of course the rudder kicked up in the middle of all the chaos.  Good times!

When we finally got things under control we decided to just motor in to Chub Cay, hope the gas didn't run out, and stay for a couple of days.  I actually added a bit of 2-stroke gas from the outboard's tank to the main fuel tank.  I figured it would be better to add it sooner, when it would be diluted with pure gas, than later, when I would have to try to run a 4-stroke on 2-stroke mix.  The real lesson for the day was that I should have tested the reefing setup more thoroughly.  And I should have waited for a weather forecast.  And I should have had an alternative plan to head northeast instead of trying to head straight out into the Tongue of the Ocean.  Behind the Berry Islands we would have had some shelter from the southeast winds and we could have made our way south as the winds allowed.  In fact the next mooring/anchorage/club east of Chub Cay (Berry Islands Club) sounded a lot more appealing in the cruising guide and had an opening to the north.  But of course none of the cruising guides consider the possibility that you can actually go through the shallows because they're written by and for deep-draft, heavy displacement cruising boats that couldn't consider a shallow passage northeast.  It was only suggested to me by a Canadian I met in Key Biscayne after the return, who had done it in his MacGregor 26.  So if you're sailing a trailerable multihull to the Bahamas, take note: you have many more options than the cruising guides allow.  I cannot reiterate this strongly enough.  If you're in a 40,000-lb., full keel cruising boat, you do NOT want to run aground, even in soft sand, because there's a good chance it's permanent or going to cost you a lot of money to get pulled off, and in the interim you're going to have a lot of expensive damage to your boat, especially if you're lying on your gunwale as the tide comes back in.  All of the cruising guides assume (correctly, for the sake of safety) that this is the kind of boat you're in.  If you're in a trailerable boat, you can pretty much go anywhere, which opens up a lot more options.  If your daggerboard is up, you have to be in 2-3 feet of water before your next warning, which is your rudder kicking up.  Once that happens, if you're still completely oblivious to your situation, you still need to get to 1-2 feet of water before you're actually aground, and then in many cases you can just jump out, pull the bow around, and push your boat into deeper water.

Another side note: I've finally gotten the mainsail handling and reefing systems nailed down, as of August 2007.  I have given up completely on roller reefing.  It simply doesn't make sense for this boat.  If I had configured a running topping lift it might have been a possibility but I still would have had problems with getting the sail slugs back into the track.  I am using a fantastic sail cover/lazy jack combination from UK Sails called the Lazy Cradle, and I use "traditional" slab reefing lines through grommets in the leach of the sail to cam cleats mounted on the boom.  For the tack I use a hook to the mast cleats, which doubles as my cunningham.  It's simple and very effective.  Unfortunately it took some hard-won experience to get it all sorted out.

I have a hard time recommending staying at Chub Cay for more than overnight.  It's absurdly expensive, and the 40-foot minimum for a slip hurts if you're 32 feet LOA.  The staff are very friendly and the maintenance man Bones found and shaped a perfect piece of mahogany to help me fix my mainsheet cleat mount (and of course wouldn't accept any payment for it, despite that fact that he wasn't going to see a whole lot of the $800 I spent there in 2 days), but the entire place is under construction so the ambience is a bit lacking.  Had I known about Frazier's Hog Cay I probably would have tried to get to the Berry Islands Club, but it was blowing 25-30 steadily by the time we got to Chub and just got worse over the next couple of days, so we were in no position to go harbor shopping.

Day 5: Chub Cay to Nassau, 38 nm

Day 5 route

We motor to Nassau after the SE winds blow out on a day with light SSE winds.  Nassau is kind of a hole, but there's a sailmaker there, and I take the sail in to see if he can fix it.  At this point I wasn't sure if we were going to continue the trip because I felt like I'd put Tanya through enough hell and we had approximately 4 hours of fun in the last 2 weeks.  I thought about flying Alex out to just deliver the boat back to Florida and letting Tanya fly down to Georgetown in the Exumas to be with her family.  We get a slip and a room at the Nassau Harbor Club, which is nice enough and really close to all of the marine shops in town, but still a bit of a disapointment since the hotel's restaurant and bar are closed, and since workmen started drilling into the concrete outside our room at 7AM.  The only thing that will drill into concrete is the eponymous hammer drill. You know things are bad when the highlight of the area is a Starbuck's, which is right across the street from the hotel and which gives you an hour of free wifi if you buy a cup of coffee.  One of the problems with Nassau is that the sidewalks begin and end at random.  Sometimes the sidewalk ends on your side of the street and begins on the other side, and you have to dart across the ring road that circles downtown, where cars drive 70 miles per hour.  At other times, buildings are built right up to the road and you have to wait for a break and then dash past a property to gain the sidewalk again.  On top of all this a Norther was blowing through with winds in the 30s for several days.  At least we had gotten here before it started.

Downtown Nassau has a clear division between where the tourists from the cruise ships (of which there were perhaps 7 in the harbor) are supposed to go and where they're not supposed to go.  After dark downtown is as deserted as lower Manhattan.  I wonder if it's deserted because of a perception of crime, or because of actual crime.  Outside of downtown there is more of a mix of cruisers and locals, but there's still obvious disparity.  It also seems that "imported" locals involved in banking, etc. are about as likely to go downtown as residents of San Francisco are likely to visit Pier 39.

Harbor cruise.
Tuck in your shirts,
hike up yr black socks
 and come ride the Thriller!
Nassau Harbor
What have you gotten me into?

Drilling Bones' mahogany
mainsheet reinforcement block
(in the hotel sink).

Day 7: Nassau to Norman's Cay, 42 nm

Day 7 route

After a couple of days stuck in Nassau (where we did manage to get some decent Chinese and Indian food) the sail is fixed by 2PM and we get out of the Nassau Harbor Club by 3.  The wind is blowing a steady 15-20 from the east but we decide to soldier on anyway because Tanya's parents have already been waiting in George Town for a few days.  We also decide to make landfall in the Exumas at a more southerly cay because there's no way we're going to get there before night anyway so we might as well sail on a close reach instead of close hauled and potentially get some protection from the big swells once we're behind some of the more northerly cays.  The swell in the ocean is fairly big but at least it's hitting us abeam instead of head-on.  I'm a little concerned about the amount of water in the leeward float since I haven't had a chance to seal the hatches yet, but the boat seems to be behaving well enough.

We arrive at Norman's Stake without actually seeing it, because it's nighttime, cloudy, and the moon hasn't risen yet.  We drop the sails and motor without incident towards the cay.  There's a sandbar on the chart that looks like it will provide good holding in around 8 feet of water.  It looks like there are around a dozen boats crowded into the space marked on the Explorer charts as an anchorage.  Another instance of the herd mentality, since they have no room to swing, and they are much more exposed to the swell and current through Norman's Cut than we are behind our little island.  Sometimes you see all these boats clustered in the same place and you wonder, "What do they know that I don't?"  And then you realize that they don't know anything you don't; they just assumed the other guy already there knows something they don't.

I would like to check out the submerged drug runner's plane the next day but again we have to press on.  Nothing like cruising with a deadline!  I check the floats and pump out maybe 100 gallons of water from the starboard float, which was to leeward and constantly getting doused with water on the trip from Nassau.  I'm going to have to figure out a better solution than the screw-in Beckson deck plates.  Maybe these?

Day 8: Norman's Cay to Big Farmer's Cay, 51 nm

Day 8 route

We have our first uneventful day of the trip.  We realize that we could press on to George Town but it doesn't make sense to go out through a cut and into the ocean at dusk, then try to get back into Elizabeth Harbour at night.  So we stop after a relatively short day of sailing (again upwind, mostly at 7-8 knots but occasionally topping 10) at Big Farmer's Cay.  Tanya has time for a swim and a sunshower and I have time to putter, drain the floats, and generally give the boat the once-over.  We eat a huge pot of pasta for dinner and are up early the next morning, where I make another stupid mistake.

Day 9: Big Farmer's Cay to Tar Bay, Great Exuma, 37 nm

Day 9 route

One of the advantages of a trimaran is that you can anchor in very shallow water, which reduces the scope required on the anchor rode.  We usually anchor by ourselves, far from other boats, so I can pay out an extreme amount of rode and never worry about dragging.  The Fortress anchor seems to hold very well and the winds have been consistent overnight as long as they've been above 10 knots or so.  The mistake was in trying to lower the daggerboard and raise the main before pulling in the anchor.  The problem is that it's impossible to get the daggerboard down once the boat is moving (resolved since the trip, by making the slot larger).  However, once the anchor is up the boat is pretty much constantly moving.  Again my stupidity is due to the fact that we're in a rush and I am inexperienced with this specific boat: if I had slowed down and taken more time we would have raised the anchor, motored or drifted to deeper water, lowered the board before we really got moving, and finally headed up and raised the main.  But I tried to do it backwards and we ended up slamming into a rock because the boat starts to sail as soon as the sail is up, even if it's luffing and the sheets are slack.  Tanya was warning me from the cockpit but I didn't tell her to ease the mainsheet because I was worried about the flogging boom hitting her in the cockpit.  Now there's a big chunk taken out of the forefoot of the daggerboard but it still goes up and down so it's the least of my worries.

The far bigger problem on this day was the rudder.  We sail out through Galliot Cut without problems, and needless to say the wind has gone southeast so it's going to be close hauled again all day.  One more argument for not planning to meet anybody while cruising, since it would have been a great day to sit around, snorkel, and wait for the wind to change.  We're still making 7-9 knots but since the board is now up there's a fair amount of weather helm, which puts a lot of load on the rudder.  Still nothing like on the Avalon, though.  We have one reef in the main and are making good progress south when there's a sudden loud bang.  It sounds like a backfire or an explosion.  I realize immediately by the strange tiller motion that the carbon fiber rudder gudgeons have cracked.  I release the mainsheet, get the engine down and running, and Tanya steers toward the Exuma islands while I lower the main and jib.  The idea is to get through one of the cuts to the western side of the islands, where we will be sheltered from the wind and swell.  Tanya figures out the nearest cut and gets a waypoint into the GPS.  We motor through Prime Cut and anchor just inside to assess the damage.  The lower gudgeon has pretty much exploded and the upper one is cracked but working.  When I built the rudder, I deliberately made the transom gudgeons stronger than the rudder gudgeons.  I reasoned that if either broke, I wanted the rudder gudgeons to break first because they're replacable.  The transom gudgeons are fiberglassed into the boat in a really inaccessible place.  Unfortunately, I didn't design the rudder gudgeons very well.  I should have built them to fit inside the rudder cheek plates, not outside, but I was adapting Farrier's design for a daggerboard rudder.  Another reason to follow the plans and not deviate!

Tanya works out a passage southwest of the cays.  It's shallow most of the way but we can make it.  Fortunately it's close to high tide.  We spend the rest of the day motoring and scrutinizing the charts.  At one point the depth sounder is reading 3 feet under the hull but we don't run aground or hit any more rocks.

Eventually we have to go back out through a cut to get into George Town.  We decide on Darling Cay cut because there's a huge sand bar, dry at low water, to the south of it, where we probably can't get through and I do not want to run aground and be stranded until the next high tide.  This turns out to be a good choice because the wind and swell have moderated and the trip in the ocean for the last 3 miles isn't difficult.  We also decide to enter Elizabeth Harbour by the Ocean Bight, despite the warning in the chartbook: "...an area of shoals and shallow coral make passage for most vessels too intricate and difficult..."  The tide is still high, and we proceed slowly and uneventfully through this passage, and eventually find the house where Bob and Sue are waving from the beach.  Again the cruising guide's advice seems to be aimed at deep-draft heavy cruising boats, which are far more likely to hit coral than we are, since we saw a lot of coral heads but none of them appeared anywhere near the bottom of our hull.

I think the real problem with the gudgeon was that early in the trip I tightened the rudder pivot bolt too much in an attempt to get more pressure on the rudder and alleviate the slop.  The problem was that this put the carbon fiber on the inside of the rudder gudgeon brackets in compression, and carbon doesn't take compression very well.  This explains why all of the damage was on the inside of the brackets, not the outside.  I'm hoping I'm right because if so it means that fixing the brackets with loads of glass and not squeezing them too much will effectively solve the problem, and they won't blow up on me again in the middle of the ocean.  (Postscript: later I replaced the gudgeons with completely different ones that comply with the designer's design instead of my own goofy rendition, and they have worked flawlessly.)

Next

Notes

Checking in, in a nutshell:
  1. Sail to Bimini.
  2. Call the marina of your choice (but near customs) on VHF and find a spot to dock.  They won't charge you unless you stay after checkin.
  3. Raise yellow "quarantine" flag on starboard spreader.
  4. Bring your passport, crews' passports, and boat registration to either Customs or Immigration and fill out paperwork.  Bring cash (greenbacks OK).  Check the Internet for how much since it's probably going to change.  It's less if you have no intention to fish and don't need fishing licenses.  Crew have to stay on the boat.
  5. You can start at either Customs or Immigration but you will have to visit both offices.  They are next door to each other.
  6. Once you've cleared, you can return to your boat and replace the quarantine flag with the Bahamian courtesy flag, which is similar to, but not identical to, the Bahamian national flag.
  7. You can stay where you are or move to one of the other marinas.
For some reason most, but not all, of this information is available on the Internet, and none of it shows up in the cruising guides.

Pinching: everybody reading this probably knows that boats can't sail directly into the wind.  Most modern boats sail within around 45 degrees of the wind, so they have to sail a zigzag course to get to a destination that's directly upwind.  Square-rigged sailing ships of yore sailed only within 70 or 80 degrees of the wind, which is why the "trade winds" were so important to trade: they allowed ships to sail downwind both ways to and from America or the Far East, by being in different parts of the ocean.

Sailing upwind is known as "pointing" and sailing as much upwind as possible is known as sailing "close to the wind", or "close hauled", because the main and jib sheets are trimmed, or pulled in, as much as they can be.  Racing boats with tricky gear like asymmetric daggerboards or canting keels can sail a few degrees closer than the average boat, and traditional full-keel cruising boats sail a few degrees farther off the wind.  Even a few degrees can make a big difference when you're trying to sail to windward.  If your destination is 10 miles directly upwind, you're sailing at 6 knots, and you make one tack, and you're pointing at 45 degrees, you will sail 14 miles and it will take 2 hours and 22 minutes to get there.   If you're still doing 6 knots but you only sail 50 degrees from the wind, it will take you about 15 minutes longer.  Over a long distance this difference really adds up, particularly since sailing upwind is the least comfortable point of sail.

The speed at which you get to your destination, as opposed to your speed through the water, is known as Velocity Made Good, or VMG.  In the first case above you're sailing over 14 miles but you're getting to a point 10 miles away, which means your VMG is only 4.24 knots even though your boat speed is 6 knots.  An interesting property of sailboats is that some attain maximum VMG when they're not actually sailing as close to the wind as possible.  In other words, for some boats, even though you can sail, say, 45 degrees from the wind, if you sail something like 50 degrees you will actually get there faster, because your VMG is better.  Another way of putting it is that you get to your destination faster by aiming a little farther from it than you could.  Ultralight racing monohulls and multihulls are particularly susceptible to this phenomenon, but it affects all boats to some degree.  Sailing "above" the point of maximum VMG is known as pinching, since you're "pinching" the wind and it stops driving the sails.  If you pinch long enough and high enough, you will go into irons, and stop dead in the water.

Come on, how often do you get to use a word like "yore"?

Most people know about four of the points of the compass: N S E W, and most know the other four points in between: NE, NW, SE, SW.  But most non-sailors don't know that there are actually 16 "cardinal" points of the compass, which gives you a good bit more clarity when you're describing wind or current direction, or a course to steer.
compass rose
Gudgeons are things that you only find on a boat.  They are basically brackets that hold the rudder in place, yet allow it to rotate to steer the boat.  Sort of like hinges.  Gudgeons have holes in them.  On most boats, pins called "pintles" attach to the rudder, and the gudgeons attach to the boat.  The pins on the pintles slip into the holes in the gudgeons and voila!  On my boat, there are gudgeons on the boat's transom and gudgeons on the rudder, and the two bolt together.