★ St Barths Bucket Regatta

01Why it matters

There is no other week in the year that puts this many of the world's largest sailing yachts on a start line at once, and very few in which their owners are visibly at the helm. The Bucket is the reference event for the sailing superyacht — the week that sets the fleet's pecking order, tests new launches in public, and gives the yards and rig makers their most useful advertising.

In our reading, the reason it has never been successfully imitated is the combination of scale and restraint. The regatta has always presented itself as a private gathering that happens to be visible, without title sponsorship of the kind that shapes the Mediterranean superyacht events, and the invitation rule keeps the fleet at a size the island can absorb. Saint Barthélemy is a small place — one runway, one harbour, no capacity to grow — and the Bucket's decision not to outgrow it is what has kept its character intact for three decades.

02The week around it

Saint Barthélemy in mid-March is at the end of its high season and the Bucket is the last large event before the island quiets down. Gustavia's small harbour fills with the competing fleet and with spectator boats anchored outside; the largest entrants lie off Gustavia or in the roads between the island and Île Fourchue because the inner harbour cannot take them. Traffic on the island's narrow roads becomes genuinely difficult in the mornings and around prizegiving time, and the airport at Saint-Jean runs at capacity.

The island's own rhythm is unchanged: shops open along the Rue de la République, the boulangeries fill early, and Saline and Gouverneur beaches stay quiet because everyone is either racing or watching. Villa rentals for this week are among the first to go in the Saint Barths calendar. Anyone not connected to the regatta will find the island busy, expensive and unusually good for watching sailing from a rock.

03When to arrive

Arrive Tuesday or Wednesday if you are involved with a boat, since Wednesday carries registration and the pre-regatta captains' briefing. For a visitor, Thursday afternoon is the practical arrival: Friday, Saturday and Sunday are the three race days, each with the same late-morning start and an evening prizegiving. Leave Monday, when the fleet disperses and flights out of Saint-Jean are easier to get. A shorter version is Friday to Sunday, which captures the racing and both waterfront parties.

04Where to stay

Gustavia itself is the only place to be within walking distance of the quay and the evening events, and it has very little accommodation; most people take a villa. Saint-Jean, ten minutes over the hill, has the largest concentration of hotel rooms and is the island's most convenient base. Lorient, Pointe Milou and Marigot on the north side are quieter and require a car. Flamands and Colombier on the west are the closest to the leeward end of the courses and give the best terrace views of the fleet coming around. Anse des Cayes and Toiny are the furthest from the racing and the calmest. There is no cheap tier on this island in March; Sint Maarten, twenty minutes away by air, is where the genuinely price-conscious stay and commute.

05Access and hospitality

Racing is by invitation only. Owners apply or are invited through the organizing committee and the Notice of Race, entry forms and sailing instructions are published on the organizer's site for entered yachts and their crews. There is no public ticket, because there is nothing enclosed to ticket: watching from the shore, from the harbour wall and from a chartered spectator boat is free and unrestricted. The evening prizegivings are crew and participant events. Charter yachts can and do enter, which is the one route in for someone who is not an owner.

06Where the social activity happens

The Quai Général de Gaulle and the harbour front in Gustavia are the whole of the week's public life — the race office, the berthed fleet, the bars and restaurants along the water, and the crowd that gathers at the end of each afternoon to watch the boats come in. The Collectivité building at the head of the harbour hosts the final awards. Shell Beach, a short walk from the quay, is where a good deal of the daytime standing-around happens. Colombier and the road above Flamands give the best free vantage points on the racing itself; the cliff path down to Colombier beach is worth the walk. In the evenings the restaurants of Gustavia and the beach clubs at Saint-Jean and Flamands take the crowd, and reservations are required everywhere.

07Getting there

08Practicalities

09History

The Bucket began as a private arrangement among a handful of large-yacht owners in Nantucket in the 1980s, raced for a trophy that was, by the founding story, an actual bucket. Wikipedia dates the first Saint Barthélemy edition to 1995 with four boats — Sariyah, Gleam, Mandalay and Parlay — and records 26 entries by 2005, by which point the Caribbean regatta had become the larger of the two. A summer Bucket continues at Newport, Rhode Island, as the northern counterpart.

The fleet's composition has changed more than the format. The 2008 entry list, as recorded on Wikipedia, was led by the 152-foot Windrose alongside the 148-foot Helios, the 125-foot Altair and the 115-foot Tenacious; the boats that now win are substantially larger and carry rigs and sail-handling systems that did not exist then. The most recent structural change came for 2027, when the organizer moved from three races with an optional extra day to a four-race series over Thursday to Sunday, explicitly because the trade winds have been less dependable in recent Marches.

10Who is there

Sailing yacht owners, who are the reason the regatta exists and who mostly race their own boats; professional afterguard sailors, including Olympic and America's Cup names hired for the week; captains and permanent crew; the designers, yards, riggers and sailmakers who build these boats and use the week to see their work sailing; charter brokers with clients aboard; specialist marine photographers and press; and the island's regular March population of villa renters, who watch from the shore.