Isbjorn Offshore: Hanging with the ‘Big Guns’ in Antigua (and feeling right at home).

'Rebecca,' the most beautiful ketch of all?

Clint and I bid farewell to the last of the Leg 2 Isbjorn crew on Thursday and have been hanging out in Falmouth Harbour ever since. It’s my first time here, and I must say, quite the place. But before I get to that, we’ve got to describe how we got here.

My last report came from St. Barth’s, where we’d just had a very strange journey across the Sombrero Passage, first reaching on a northerly, then becalmed, then sailing into Ile Fourche on a southwesterly. What a relief from the head-banging to windward we had for 200 miles on the ill-fated Leg 1!

But it wouldn’t last of course, couldn't last in the Trade Winds of the Caribbean, and our departure from St. Barth’s was upwind yet again, almost a dead beat to weather into a moderate southeasterly.

The crew was slightly hungover from a big night at Cheeseburger in Paradise, but we didn’t plan to leave until late afternoon, so they had time to sleep it off. We changed down to the small headsail while still on anchor, then hoisted the mainsail and sailed off the anchor and around Gros Islet to the west. The new furler is longer than the old one by five inches, so the swivel doesn’t hoist as high as it should (the sail’s luff is too short). This causes the halyard to wrap around the headstay, basically the worst thing that can happen to a furler (and the most common cause of failure), so Clint went aloft almost before we were out of the harbor to clear the wrap, and just in time before darkness fell. Boat first, remember? 

We hauled him up on the port spin halyard, with the spare jib halyard clipped to his harness. Greg skillfully kept Isbjorn on a close-reach to keep the boat at a stable heel (it’s much easier to go aloft upwind than downwind, believe it or not), while Ryan & I handled the halyard and Andy Staus took up slack on the spare jib halyard. Once at the masthead, Clint attached the spare halyard to the swivel so we could take the tension off the wrapped jib halyard, unwrap it, and re-attach it. By attaching a 10-inch dyneema pennant to the tack of the sail we were able to hoist the swivel high enough to prevent future halyard wraps, a critical job to complete before next week’s Caribbean 600 race.

Clint loves going aloft - it was the second time he’d been up offshore (the first just for fun) - so it was exciting times for him. My dad came up with a good line today about sails and boat sizes - “If you can’t handle the sails without complicated technology like hydraulics and electric winches, get a smaller boat or get better crew!” Clint’s the latter.

As an aside, when I worked at Southbound as a rigger, I learned an easier way to go aloft. The rigger ‘climbs’ the shrouds and halyards, using his feet on the mast and doing a series of pull-ups on the halyards and shrouds while one or two people simultaneously take up the slack at the mast, with two wraps around the winch. This is much faster than winching a person aloft, and leaves the climber in control, which is a critical safety mechanism. To lower the rigger down, two wraps on the winch is plenty - any more and it gets very jerky. Two wraps allows a nice and smooth, controlled descent. Of course the person aloft should always be hanging on to something on the way down just in case, and the crew on deck should NEVER un-belay the halyard or start lowering until the rigger aloft gives the okay. As in all things sailing, communication is absolutely key to a safe landing back on deck (Mia always lowers me just to the point where my toes touch the deck but I can’t get stand up. She holds me there for 30 seconds too long and gets a good laugh. Apparently it never gets old, even after the 100th time). 

In Antigua we met the crew from Scarlet Oyster, a very competitive Oyster 48 that will surely win it’s class in the 600 next week (I know them from the ARC rally).

“We go aloft at least every other day on a long offshore passage,” co-skipper Mark says. “It’s preventative. Chafe happens fast, and we go up to make sure it’s taken care of before it’s a problem.” There’s a reason they’re winners.

Anyway. Once the halyard was cleared Greg brought Isbjorn back up to close-hauled (we got good at that!) and we pointed the bow south, about the best course we could make in the 15-knot southeasterly. With one reef in the mainsail plus the small jib and we easily made 7.5 knots through the water in relative comfort compared to Leg 1.

I never take the first watch on offshore legs, instead making sure the boat is on course and clear of danger, then letting the crew take over so I can get some rest (a good sleep always cures any lingering seasickness I might be feeling). Ryan and Mike took over as the sun went down, with Greg and I on again at 2100. Our ‘playing field,’ so to speak, was dictated by the wind direction and the position of St. Kitts & Nevis to our south, and Barbuda to the east. I marked a boundary on the chart, a simple dotted line about 7 miles off the coast of St. Kitts, and told the guys to plot us on the passage chart every hour and tack once they crossed that line. It would give us plenty of room off the lee shore of St. Kitts and allow me to sleep soundly knowing they understood their instructions.

By 2030 I was woken up by the tack, which came right on cue. Mike & Ryan had made good time on their watch, covering over 21 miles in 3 hours, or better than 7 knots average speed (though unfortunately on a course of about 190º true, not exactly great but all the wind would give us. Our rhumb line was 130º true).

Greg and I took the first fully dark watch on starboard tack this time, and rode it out uneventfully until midnight. Greg, as I’m finding with most of the crew members I share a watch with on Isbjorn, would not let me near the wheel! I was relegated to ‘gopher’ status, making coffee and sandwiches and hanging out under the dodger and protected from the spray. There is nothing I like more than watching crew new to ocean sailing grinning at the helm and losing focus of their compass course because there are so damn many stars to look at! I get to re-live the magic of that first offshore passage through every new crew’s eyes. It’s the greatest job in the world.

Clint and Andy Staus took over from 1200-0300 after Greg and I tacked back onto Port. I drew another dotted line a bit further south now on St. Kitts, and by dawn we were aiming again for Barbuda on starboard. Greg and I held on to that tack until we were almost in sight of the island, some 5-7 miles off, the depths dropping below 70-feet at times as it shoaled up far offshore of the sandy outpost. One more tack sent us barreling on port right for Jolly Harbour, our destination in Antigua.

By the time we closed the island and came within sight of Antigua the wind had built to a steady 18-20. We took a second reef in the main, and really needed to roll the jib in a bit in the gusts. We carried on this way right into Jolly Harbour, dropping the hook right behind the aforementioned Scarlet Oyster, who’d only arrived some ten minutes before us, close-reaching down from Barbuda.

It was Ryan’s last night, which was a shame, because the meal we enjoyed together ashore was overpriced and understaffed, and unfortunately, that’s all Ryan is going to remember from Antigua, for he flew out the next morning.

After Ryan left, the rest of the boys readied Isbjorn for the 15-20 mile beat around the island and into Falmouth Harbour. I assigned Greg the captain’s role, with Mike navigating. Mike was looking to get more navigation experience, and Greg is returning to the BVI in a few weeks to skipper his own boat with his family for the first time in a Sunsail flotilla. There is not better way to learn than to assume the actual roles, with real stakes involved, so I took a backseat and let the guys have at it.

Mike plotted us a conservative course around the outlying reefs off Jolly Harbour and consulted with Greg on the plan, and off we went. Once around the southwestern point of Antigua the wind and seas built considerably. I’d gently encouraged Greg to hoist the main with two reefs instead of one, wanting him to take a ‘wait and see’ approach, as Jolly Harbour was pretty protected and not a good indication of what the wind was really doing offshore. He was thankful!

In open water we saw the biggest seas of either leg so far. The wind was 20-25, with 6-8 foot seas and the occasional ten-footer crashing over the foredeck. Isbjorn excels in those conditions upwind, though she’s wet! Mike was suffering at the chart table trying to plot us on paper as we closed the southern coast on one tack, then headed offshore on the next, working our way east to Falmouth.

“You can’t use the iPad until you can do it on paper,” emphasized Clint, who learned the hard way himself taking Arcturus across the Atlantic with us in 2011. To his credit, Mike never quit, jumping down below and counting off the latitude and longitude until his face was literally green. But he never barfed, and five hours later we were anchored safely in Falmouth Harbour, with Greg and Mike basically navigating Isbjorn there unassisted and sailing past the cliffs and into the harbor. Kudos to both of them.

It was the last time they’d sail the boat. Once the sails we’re furled we took a quick harbor tour before dropping the hook. What a place! I’ve seen a lot of super yachts during my travels, but never this many in the same place. Ranger, the J Class we saw in St. Barth’s is here. So is Comanche, the 100’ maxi that just won the Sydney-Hobart Race. Phaedo3, the fluorescent green and mirror-silver MOD 70 trimaran that set the 600 course record last year in 33 hours (!) is moored alongside the yacht club’s cafe. Inukshuk is here, the schooner Gloria, the plumb-bow pilot ketch Hetairos which I last saw in Horta in 2012 are all here. Rebecca, arguably the world’s most beautiful ketch is here. The list goes on, and they’re all in the same marina at Antigua Yacht Club.

This is going to sound arrogant, but I feel like I really belong here. Not the boat (though I’ll admit Isbjorn does stand out in the anchorage as a true classic, albeit a small one in this company!). But walking the docks and seeing the crews of like-minded people out here living the dream is strangely comforting. I could never work on a super yacht, but everybody here is of the same mindset. Owners and charter guests aren’t around (as opposed to St. Barth’s), so everyone is relaxed and underdressed and the atmosphere is mellow. The bars and restaurants ashore are not pretentious, but have a laid-back Caribbean style, still more up-market than the local villages in St. Lucia or Dominica, but still shorts and flip-flops friendly. You can eat breakfast at the Seabreeze Cafe on the dock and be rubbing elbows with Volvo and AC sailors here for the race, and everyone is just a normal person. 

It’s a different atmosphere from your standard cruisers hangout. Here, everyone is a professional, and acts the part. There’s debauchery to be fair, but it all just seems a little classier, and I don’t mean that in a fancy-pants pretentious way. The crews I’ve met here know their jobs, do them well (this is the best of the best here after all), and have fun doing it. And there’s a ton of young people (Lee Cumberland, this is where all the young folks are!). I feel much more at home here amongst this crowd than I do in the more cruiser-friendly, and always older, Caribbean haunts.

I was almost one of the crew I write about. In Ireland after crossing the Atlantic on Arcturus, Mia and I were out on a hike and stopped on a cliff overlooking the Irish Sea to reflect on our passage and discuss the future. We’d take the boat to Sweden and start looking for work on a big sailing yacht, we decided then, high-fiving to seal the deal. Ideally a boat small enough where we could run it as a couple with no other crew. Save some money and see the world.

But I’m partially colorblind. I can see color well enough to be a captain in the US merchant marine, or even a fighter pilot in the Air Force. But the MCA in England, which administers the commercial part of the Yachtmaster qualification (of which I’m in the highest, ‘Ocean’, category) has different standards for their testing requirements. I can’t pass it. Something like 80% of super yachts around the world require the commercially endorsed Yachtmaster license, which in turn requires that dammed color test.

This was a huge blow. I went so far as to fly to England in 2009 to take the only re-test that the MCA allows, hoping I’d make it past the second screening (which is a different test). I didn’t (I stayed with Clint on that journey). 

But in hindsight, it was a blessing. I wouldn’t own by dream boat right now, sitting here in Antigua and writing about this if I had perfect color vision. I might well be one of the crew on Ranger and dreaming about that beautiful Swan 48 out in the harbor with such a cool crew onboard, sailing where we damn well please when we damn well please, and dammit, the stainless steel is shiny enough! Everything happens for a reason, baby.

Alas, we won’t be here for long. I was hoping for a good ten day rest to put the boat back together and hang out with Clint, do some meditation, some running, explore ashore, cook food. We’ve had a few days of that to be sure, and it’s been awesome. But it will come to and end tomorrow when we’ll raise the anchor after dinner and point the bow downwind (for once!) and towards Sint Maarten. Isbjorn’s new mainsail will be waiting for us (I hope) on Tuesday, courtesy of Chuck at Chesapeake Sailmaker’s who expedited the sail’s production in South Africa after our misfortune on Leg 1. Now we’ve just got to go and get it.

My dad flew down on Friday to do the 100-mile passage there and 150-mile beat to get back, so it’s been fun having him here, and will be nice to have a third watch-stander at sea. With luck, we’ll have the new mainsail fitted and be back in Falmouth by Thursday, just a day before the new crew turns up for the Caribbean 600.

Follow our progress on the way to Sint Maarten and during the race on You can also follow the race itself on