Please select your home edition
Edition
Maritimo 2023 S600 LEADERBOARD

A Caribbean Tale - Annie

by Lindsay Wright on 12 Nov 2007
CaribbeanMap SW


The old charter yacht looked utterly forlorn; like a maritime little orphan Annie.


She was tied to the dock at Road Bay, on the Caribbean island of Tortola, by chafed and faded docklines. Her fibreglass hull was scarred by minor collisions, chalky from neglect and a marine biologist’s dream of flora and fauna fanned out from her bottom in the limpid water of the marina.

Belowdecks an oily cavity remained where an engine had been and tumbleweeds of ripped out wiring hung from holes in the bulkheads where electronic equipment had been removed.

Roger, who had just bought the boat, sight unseen, from another island, St Maarten, didn’t look a hell of a lot better. I found him slumped over a beer in a nearby bar, looking like a bridegroom who has just found out that the woman beside him at the altar was that months Hustler magazine centrefold.

We both worked for a yacht charter company in St Maarten, part of a team of mostly Kiwi yachties who earned a living piloting tourists around the reef strewn waters of the eastern Caribbean and I’d agreed to help him get the boat back to the St Maarten.

Roger mumbled about waiting for a northerly and continued tracing palm trees in the pool of condensation puddling the bar around his beer glass. A northerly….it was March in the Caribbean and the nearest northerly could be months away – I had an overnight delivery trip in mind….not that sort of time frame.

After a few beers and some intensive cajoling, I bullied Roger down the dock to his boat where he lurched around the deck for a while, sighed and started to poke at the sun faded sails dumped on deck. We began readying the boat for sea.

All this activity attracted a bit of interest from people around the marina and the skipper of a nearby yacht ambled over for a yarn. 'Goin’ somewheres?' he drawled. 'St Maarten…' we said. 'In that thing?' he replied incredulously and walked away shaking his head.

As we worked, a tall, bearded and ear-ringed seafaring looking sort of bloke appeared on the dock. 'Hi,' he said in a sharp east USA accent, ' the name’s Tommy - I hear you guys are going to St Maarten.' We nodded. 'Well, that’s great,' he continued, ' can I hitch a ride?' And he went on to extol his broad experience in all kinds of craft and his virtues as a knowledgeable and energetic shipmate.

It pays to be wary of hitch-hikers in the Caribbean. We’d heard all the stories about drug smugglers and Americans bearing firearms but, well, many hands do make light work, particularly hand steering a lame duck like we would be doing…and we had nothing to steal...so we welcomed Tommy aboard.

'Thanks guys,' he said, and settled himself in the cockpit to oversee our preparations, offering advice and everything except a hand.

When we were ready, we hailed the crew from a nearby super yacht, who towed us out of the marina with their big inflatable dinghy. Once in open water, we winched the battered old mainsail up the mast. 'Hope she lasts ‘til St Maarten mate,' Roger said ruefully. The roller furling jib didn’t look much fitter than the mainsail, but we sheeted them in and got the boat wallowing in the right direction while Tommy continued his monologue.

'Gee guys – this is just great,' he said, basking in the cockpit as Roger and I tacked through the boats anchored in the smooth waters of the bay.

After a while we sailed between two small islands and the boat wallowed up and over the first lumpy sea of the Anegada Passage. That wave left the several thousand barnacles that were clinging to the boat’s bottom – and Tommy - gasping for air. But it had just about the opposite of the desired effect. The barnacles stayed where they were and Tommy went to bed.

'Aahh, see you later guys,' he said with a dismissive wave of his hand and disappeared below.

The passage from Tortola to St Maarten is about 90 nautical miles ( 167 kilometres); straight into the prevailing trade winds, against the north equatorial current and the steep seas of the Anegada Passage. The big charter yachts motorsail it overnight and the average cruising boat will take about 30 hours to cover the distance. It took us 60.

During the first 20 hours, Tommy appeared on deck three times, poking his pallid face through the hatch to ask which island the blaze of lights on our starboard side indicated. The answer was the same each time : 'St Croix.' After the third time, he groaned despairingly and became permanently prone.

Roger and I took turns steering for the first 40 hours, catnapping in the cockpit, yarning and enjoying the warm soft tropical air. Eventually the beer ran out and we decided that we really needed a third hand. Roger went below and roused Tommy who raised his bedraggled head 10cm off the pillow and fixed him with bleary eyes. 'You’re looking at a sick man,' he groaned, slumped back and rolled over. I tried a more aggressive approach, threatening to douse him with buckets of seawater but met with a similar result.

The boat sloshed sickeningly onwards. We abused Tommy from the cockpit, related stories of seasick young girls who had taken their turn at the wheel on Atlantic crossings, threatened to drag him out of bed and lash him to the wheel, but all Tommy did was groan.

A few hours later as we lurched across a star freckled sea, a loud and ominous splashing noise came from below. I looked quizzically at Roger….he looked quizzically at me – each daring the other to investigate. He lost – it was his boat after all – and disappeared down the hatch. Minutes later his head reappeared….'looks like we’re sinking, mate,' he said.

This bald assessment of our situation was greeted by a series of wailing noises from the cabin where Tommy lay, but he must have quickly reconciled himself to meeting his fate because he didn’t stir from the bunk.

Roger launched into a feverish bout of activity and found an open through hull fitting we hadn’t noticed, high on the hull behind some smashed joinery, which was swallowing a prodigious amount of seawater every time we lollopped over a wave. We tacked the yacht to put it on the high side, stuffed a rag in the hole, and took turns pumping the water out. Tommy slept.

Hours later we raised the peak of Saba (pronounced Sayber), the steep volcanic pinnacle that rises from the seafloor south of St Maarten. Tommy’s tousled and haggard head appeared in the hatchway. 'What island is that?' he asked. 'St Croix mate,' Roger replied, quick as a flash. A pitiful look of abject despair slunk over Tommy’s face as he moaned and slunk back to bed.

Just on dusk we sailed into Groot Baie, St Maarten, rounded up into the wind, dropped the anchor and cadged a ride ashore with yachties from a nearby cruising yacht. Tommy stayed aboard and the next day he was gone, thought it was obvious he still hadn’t learned how to operate the toilet.

Roger renamed his boat Carawak and moved her into the marina to begin the long refit that would transform her into his cruising home. A month later, as he bent over the shiny new diesel engine, a shapely young lady in a barely adequate bikini sauntered down the dock and stopped to talk. 'Did this boat used to be in Tortola?' she asked. Roger nodded. 'That’s right,' she said, ' that’s where I’m from. I know the guy who skippered it up here – Tommy - he said it was really rough – his crew were seasick the whole way.'

C-Tech 2020 Battens 2 728x90 BOTTOMSelden 2020 - FOOTERNorth Sails Loft 57 Podcast

Related Articles

America's Cup: Kiwis advertising for key people
Emirates Team NZ seeking new people for key roles ahead of its 12the America's Cup campaign Emirates Team New Zealand, the current America's Cup champion is gearing up for the 2027 Defence of the most prestigious trophy in sailing. The team has advertised eight positions in the IT, Meteorology and Engineering areas
Posted today at 9:54 am
Bronze for Baltimore Sailing Club in New York
As Ireland Shines on World Stage at 2025 Team Racing World Championship Ireland's Team Racing Team Baltimore Sailing Club from West Cork has claimed the bronze medal in a gripping finale to the 2025 Team Racing World Championship, held at the prestigious New York Yacht Club.
Posted today at 5:46 am
Russell Coutts explains SailGP's investor value
Russell Coutts explains the growth of SailGP and why investors are chasing a slice of the action. SailGP co-founder and CEO Russell Coutts was interviewed last week, ahead of the weekend's Mubadala New York Sail Grand Prix, where he discussed the hard to understand investment, and growth of SailGP.
Posted today at 3:27 am
5.5 Metre World Championship Day 3
Aspire is new leader in Sopot Aspire (POL 17, Przemyslaw Gacek, Mateusz Kusznierewicz, Kilian Weise) has taken a 10-point lead at the 2025 5.5 Metre World Championship in Sopot, Poland, after two more races on Wednesday in a cold northerly between 12-23 knots.
Posted on 11 Jun
WingFoil Racing World Cup Switzerland day 2
Rising stars and tight battles on Lake Silvaplana Day two of the Wingfoil Racing World Cup Series in Silvaplana delivered another spectacular day of competition, despite a short initial delay as racers waited for the wind to fill in.
Posted on 11 Jun
2025 Star Class Europeans opens in Viareggio
Stipanovic and Cayard share the spotlight The Star European Championship 2025 got underway today in the waters off Viareggio, with two races sailed in light and tricky conditions.
Posted on 11 Jun
Introducing EDGE - Your All-Around Advantage
North Sails 3Di Endurance Edge - from Regatta Starts to Sunset Sails North Sails 3Di Endurance Edge - from Regatta Starts to Sunset Sails. EDGE is as ready for regattas as it is for day sailing. Lighter and lower stretch than paneled or string sails. Integrated ENDURANCE Surface™ delivers a durable and easy-to-handle sail.
Posted on 11 Jun
The Ocean Race Europe to contribute ocean data
All of the competing IMOCA race boats will carry specialised science equipment The Ocean Race Europe, an offshore sailing race that connects seven European cities from the Baltic to the Adriatic Seas will see all of the competing IMOCA race boats carrying specialised science equipment.
Posted on 11 Jun
Loro Piana Giraglia 2025 Offshore Race Start
A total of 97 yachts are now racing along the 241-nautical-mile course At exactly 11:55 this morning, the starting procedures kicked off on the line off Saint-Tropez, sending the fleet toward the Giraglia rock.
Posted on 11 Jun
Foiling Week 2025: A stellar edition set to launch
Five classes will compete: Moth, WASZP, Switch One Design, BirdyFish, and ETF26 Foiling Week returns to Europe for its 12th edition, taking place in the last week of June, after its first-ever event in Pensacola, Florida, earlier this March.
Posted on 11 Jun