How to plan it: A tactician’s guide to the St Barths Bucket

Tony Rey, veteran tactician of America’s Cups and round-the-world campaigns, explains how superyacht owners can prepare for the St Barths Bucket. From crew selection to race-day strategy, he shares the secrets behind success – and why the event is as much about enjoyment as competition.

It begins, as the best Bucket stories do, in the middle of a race. Vijonara is fully pressed, sheets loaded, the owner on the helm, spray coming back along the side decks, as the sounds of Chopin filter into the cockpit. For the sheer fun of it, the owner has invited a concert pianist to play the yacht’s Steinway baby grand during the race.

“It was completely surreal. It was one of those ‘only at the Bucket’ moments,” recalls Vijonara’s tactician, Tony Rey.

It’s the sort of story that gets told at the bar later: the 39-metre modern classic yacht under full sail, a crew working hard and something quietly eccentric threading through it all. For Rey, it captures much of what the Bucket is about: serious racing, taken seriously, but never so much that it stops being utterly enjoyable.

Rey has raced almost everything worth racing, from America’s Cups to maxis and round-the-world campaigns, yet the Bucket holds its own particular charm for him. As he talks, you begin to sense why so many owners return: the mix of power, camaraderie and sheer enjoyment that, for a few days in March, turns St Barths into something quite special.

A tactician’s eye

“For me, the thing about doing the Bucket is that it’s a really unreasonable thing,” Rey says, with clear affection. “You’re racing a fleet of large boats with very different design briefs and asking them all to race together. But that’s part of the joy of it.”

He’s talking about a line-up where a 56-metre Perini Navi might find itself pacing a high-performance 30-metre Swan, or a modern carbon sloop falls into step with a beloved cruising ketch.

The result, surprisingly often, is genuinely close competition. “After 25 miles, it is not uncommon to see boats finishing six or eight minutes apart,” he says. “Some of the most exciting moments are when you have a couple of hundred tonnes of yachts coming into the same mark at the same time. That’s where racing experience counts.”

If there is a single message Rey wants prospective owners to hear, it’s that a good Bucket result starts long before the first warning signal. “Sometimes the expectation of the resources needed can be a little bit low,” he says. “To do it properly you need a lot of resource in terms of crew, preparation and logistics. The Bucket is not something you can just turn up to on a whim and expect everything to fall into place.”

Building the right programme

The first decision is often which class to race in, and how ambitious to be. “Owners and guests are usually people who are used to winning,” he says. “If they win in their first year, there can be an expectation that they’ll win every year. But it’s rare that that happens. There are simply too many factors acting on the boats. It’s important to understand that from the start, and build a programme around learning and enjoyment as much as the result.”

Crew numbers and roles are the next building blocks. “On a big boat I’ve raced with 40 people on deck,” he says. “You’ll typically have a core of professional sailors – trimmers, bow team, pit, a navigator – then the captain, engineer and permanent crew, plus the owner and guests. Getting that mix right is crucial.”

However ambitious the programme, Rey likes to create a rhythm around each race day. “We debrief every day,” he says. “That’s a really big part of it. The aim is that we learn something every single day we go sailing. Each day is partly about working out what we don’t know yet. If you can be honest about that, you can improve very quickly. Owners really appreciate that approach. They like to see that there’s a process, that you’re not just turning up and hoping for the best.”

His briefings always start in the same place: loads, limits and responsibility. “The captain and the engineer really need to know that boat inside out – where the mainsheet load maxes out, how far you can push the rig, what the gear can take. They have to understand those limits and pass them on to the crew.”

On a big superyacht, command isn’t a simple, single line. “You’ve got a lot of people on deck,” Rey says. “So we split the boat up by area – foredeck, mast, pit, aft – and we’re very clear who’s in charge of each zone. That’s the only way you can push hard and stay safe.”

Something to witness

For owners and guests, the first realisation usually comes the moment the boat is fully pressed. “When someone’s
on board for the first time and they feel that power, it’s a huge thrill,” Rey says. “One of the most common comments from guests who’ve never been on board before is how struck they are by the teamwork, the co-ordination, the professionalism. 

They’re used to seeing that kind of thing in their business lives, but seeing it on deck, in that environment, is different. It’s incredibly transferable, with skills such as communication, trust and responsibility, and they spot that very quickly.”

From his vantage point as tactician, Rey sees the atmosphere shift over the course of the regatta. “By the end, the crew and guests usually feel like a family,” he says. “It’s quite an intimate experience, which sounds odd when there are 30 or 40 people on deck, but you really do come together as a crew.”

That sense of shared purpose extends beyond the racecourse. “The parties are spectacular,” he says. “The prize-giving is hard to describe to someone who hasn’t seen it and it’s on a scale that’s difficult to imagine. A first-time guest at the Bucket is going to see some very special things. It’s a fantastic, very experiential few days.”

Bucket moments

For all the talk of process and parameters, Rey hasn’t lost sight of the less quantifiable moments, the ones that tend to stay with people long after the results sheet has been forgotten. “I’ve seen some remarkable things out there,” he says. He remembers a day when a whale breached close across the bow; others when the sea has been alive with flying fish and dolphins pacing the boat for miles at a time.

For Rey, those flashes of unrehearsed theatre are the point. “It connects anybody on board to the archetypal joys of sailing,” he says. “The adding of a bit of risk to everyday life, that sense of doing something slightly outside your normal pattern – there’s a lot of magic in that.”

For anyone considering pointing their bow at St Barths, his advice is simple enough: do it properly, then allow yourself to enjoy it. The format, the island and the people behind the regatta have created something rare: a week where very large yachts can race hard, safely and in good company. It is, in Rey’s view, the sort of experience every owner should try at least once.

First published in the March 2025 issue of BOAT International. Get this magazine sent straight to your door, or subscribe and never miss an issue.