Why Travelers Should Set Sail for St. Barths Bucket Regatta

“Why do you go all the way to the Caribbean when Hawaii is so close?”  is a question I’ve been asked many times since I began traveling from California to the Caribbean decades ago. While the proximity of Hawaii’s beaches certainly entices, the Caribbean’s soul and flavors seduce me like the irresistible scent of freshly baked pastries wafting from a Parisian boulangerie. And, Saint Barthélemy, the distinctive crown jewel of the Caribbean, tempts like no other island.

Commonly called St. Barths, St. Barth, or St. Barts, the tiny French island is worth the journey, whether it’s your only destination or you are island-hopping. Known for its mesmerizing turquoise and deep indigo waters, white sand beaches, luxurious hotels, world-class villas, gourmet restaurants, and designer shopping, St. Barths also famously draws the world’s most spectacular superyachts each winter to its Gustavia Harbor.

St. Barths Bucket Regatta, Credit: Ed Gudenas

During my recent trip to the island of St. Maarten/St. Martin, I took a breathtaking, 15-minute flight from Princess Juliana Airport on St. Maarten to the chic island for a weekend during the 2024 St. Barths Bucket Regatta, a must for superyacht racing fans. After originating in Nantucket in 1986, the Bucket debuted at St. Barths in 1995 and has grown into the island’s second most popular week behind its legendary New Year’s Eve festivities. Every March, elite superyacht sailing vessels and their billionaire owners, along with crème de la crème sailors and well-heeled spectators, flock to the 8-square-mile island for an exhilarating three days of racing powered by reliable trade winds and set against the picturesque island backdrop.

Viewers congregate to watch the ballet on water from hillside villas, Fort Karl in Gustavia, coastal roads, and their own personal or chartered yachts. The Bucket participates in Clean Regattas, the world’s leading sustainability certification for water-based events, and donates a portion of the entry fees and proceeds from the sale of the popular Bucket posters to local charities.

This regatta is renowned for its unique tactical challenges. Back for the sixth time was San Francisco native Paul Cayard, a celebrated yachtsman and professional sailor who first participated in the Bucket in 2014. He’s won multiple times as the tactician for the 56-meter Rosehearty, originally commissioned by Rupert Murdoch and now owned by Joey Kaempfer.

“The people who own these boats like to go cruising on them,” Cayard told me. “These are the owners who enjoy the luxury of their boats and once or twice a year they get their heart rate up when we bring a competitive team on the boat. Joey gets all excited about the race.”

Paul Cayard
Tactician Paul Cayard (center left) and Captain David Hutchinson, surrounded by crew, hold the trophy after Rosehearty won her class in 2019. Credit: Ed Gudenas

M5, the world’s largest single-masted sailing yacht at 78 meters, was among the 30 superyachts competing for this year’s coveted overall Bucket award and trophies in their class. A previous competitor, The Maltese Falcon, the iconic 88-meter sailing yacht commissioned by her first owner Tom Perkins, was one of five non-racing social entries and welcomed special guests onboard.

The presence of massive motor yachts, including Rising Sun, the 138-meter yacht sold by original owner Larry Ellison to David Geffen, and 116-meter Multiverse, anchored in the bay facing Gustavia and nightly dockside fun with a welcome party, Bucket Bar, Bucket Bash with live music and dancing, crew party, awards ceremony, and more combined to make the 30th edition of this regatta truly special. Events such as the owners party were by invitation only, but most activities were open to the public.

It’s no wonder St. Barths’ hotels and restaurants were at capacity, and Cayard is a regular at the event. He sits on the board of AmericaOne Racing, a developmental program focused on supporting young athletes along Olympic and other high performance pathways. The nonprofit also supports Bay Area Association of Disabled Sailors and Treasure Island Sailing Center. He also serves as as president of International Star Class and consults for Translated, a Rome, Italy-based company presently fielding a team in the Ocean Globe Race, an 8-month adventure around the world for ordinary sailors on normal yachts. Cayard, a two-time Olympian, seven-time world champion, seven-time America’s Cup sailor, and member of the Bay Area Sports Hall of Fame, enjoys St. Barths so much that he has visited without sailing.

“I love the island,” he says. A dual citizen of France whose father is from Paris, the yachtsman reminisced about summers spent with his Parisian cousins at his grandmother’s house in Sainte-Maxime in the south of France from the ages of 10 to 15.

When he’s on St. Barths, he begins each morning with a walk to Shell Beach, one of the more popular beaches, for a 25-minute swim and is reminded that the island is home for 9,000 people.

“I see moms dropping kids off at school,” he says. “Of course, there’s the excesses with the Louis Vuitton and Prada shops, but there’s a real, home-grown life to the island. That’s the underlayer of this glamorous, ritzy, billionaire aura. It has a true core, real people doing real things in a very European style. I see that and feel that. Sometimes I hallucinate about living there.”

Paul Cayard
Landing on St. Barths offers thrills due to the 2,119-foot runway ending at the sea and the sharp descent due to a steep hill on the other side. Credit: Tourism St. Barts

A certified pilot, Cayard has even done the unimaginable on St. Barths: land an aircraft on the island’s notoriously short runway that is a mere 2,119 feet and ends at St. Jean Beach where sunbathers soak up rays and the aviation action. While pilots need special certification to take off and land on St. Barths, Cayard was allowed because he was accompanied by the instructor who taught him to fly 25 years ago and has the proper credentials.

“I love flying, and that airport is so intriguing and challenging,” says Cayard, who usually doesn’t land on runways under 3,000 feet, but managed three landings on St. Barths.

St. Maarten’s airport (on the Dutch side) accounts for the majority of the approximately 140,000 passengers who arrive by air on St. Barths each year, but there are also nonstop flights from St. Martin (on the French side); San Juan, Puerto Rico; Pointe à Pitre, Guadeloupe; Antigua; Anguilla; and St. Thomas. For travelers who cannot handle the thrill of an aircraft’s sharp descent onto St. Barths runway with the sea so close, the ferry is another option to reach the island.

St. Barths closes for the season at the end of August and reopens in early October. Mark your calendars for the next two Bucket regattas: March 13–16, 2025, and March 12–15, 2026. Or, if you just can’t wait until next year, the St. Barths Gourmet Festival takes place November 5–10, 2024, and is a delicious reason to visit this fall.


Courtesy: Oetker Collection

The illustrious Eden Rock St. Barths, in the town of St. Jean, celebrated its 70th anniversary in 2023 and continues to draw glitterati from around the world. Guests have a choice of 37 individually decorated rooms, sumptuous suites, and stylish villas located on the rock or beach or within the lush beachside gardens. Some accommodations, including the 16,000-square-foot Villa Rockstar which sits securely behind a 3-meter-high wall and the James Suite, boast their own private pools. There’s also 24-hour room service, cuisine created by chef Jean-Georges Vongerichten at its Sand Bar restaurant, a spa, fitness, boutique, extensive art collection, and an ongoing Eden Reef coral restoration project. The hotel offers complimentary masks and snorkels to visitors eager to explore the Eden Reef and discover the coral growth with their own eyes.

Opened in 2014, Cheval Blanc St-Barth, with its discreet entrance from the road, contemporary style, and verdant gardens, sits on Flamands Beach on the north point of the island. Part of the LVMH group, the palace offers 61 luxurious rooms, suites, and villas. For the ultimate in privacy, book the 5-bedroom La Villa de France, spanning 6,888 square feet over two stories with an infinity pool on each floor, two terraces, 360-degree views of the sea, and a private treatment room. Dining at the popular La Case restaurant and La Cabane at the edge of the sea is a tantalizing treat as are the Guerlain rituals at the spa.

Courtesy: Hotel Manapany

Escape into nature at the Hotel Manapany, a 5-star, eco-friendly resort on the private palm-fringed beach of Anse des Cayes. Gustavia Harbor is only five minutes away, but seems a world away once you enter the property. Nestled between a tropical nature preserve and the turquoise ocean, Hotel Manapany exudes serenity and an authentic island lifestyle. All 43 rooms, suites, and villas face the sea, each with a private terrace and Instagramworthy views. Some suites offer outdoor showers and a private beach, while the Ocean Prestige features a jacuzzi.

The eco-responsible mission of B Signature, a French luxury hotel and resort group, is apparent, from Manapany’s soft towels and robes made from bamboo to the furniture handcrafted by local artisans throughout the property to the solar-powered water heating. The Green Key-certified resort produces its own drinkable water, only allows electric cars, and grows onsite many fruits, vegetables, and herbs used at its two restaurants. Put your toes in the sand at Sandy Beach, open for lunch, and feel free to feed the friendly turtles that plod by your feet. The spa features an adults-only lap pool, exclusive organic products from Dr. Hauschka, and a picturesque deck where complimentary yoga and Pilates classes are offered each morning. Surf lessons are also available for guests and day passes for visitors.


Credit: Bryan Lambert, Sebastien Poyato, Romeo Betancourt (food & drink)

Cayard’s favorites include Bonito, where chef-owner Laurent Cantineaux’s signature French Pan-American culinary creations dazzle as much as the restaurant’s views of Gustavia and beach house interiors, and L’Isola, where perfectly cooked, fresh, homemade pasta, delicious tiramisu, and Italian staff transport diners to Italy. Also on his list: Bagatelle, noted for its scrumptious Mediterranean cuisine and convivial atmosphere, and La Petite Plage.

For a unique and immersive dinner experience, reserve the Chef’s Table by Jean-Baptiste Piard at Zion, where a pathway through a tropical garden leads to utopia. With a surprise, 7-course menu (wine pairings optional), the notable chef known as JB keeps his guests wondering what delectable dish is next as he converses with and serves them from the counter connected to the open kitchen. With only six seats available nightly, foodies should book far in advance to enjoy this cooking show.

Zion Chef’s Table

For the best beach club dining, head to Nikki Beach, a favorite of celebrities who come to feast on Caribbean-flavored dishes and Nikki Beach’s signature dishes. Relax on the all-white, plush sun beds and enjoy the energy and music that grows louder as the afternoon progresses. Two doors down and not to be missed is Gyp Sea Beach Club. A festive atmosphere, friendly staff exotic cocktails, deejay, and mouthwatering cuisine, including yummy hamburgers and seafood right off a barbeque grill, combine to make this a memorable beachfront experience.


Gustavia is not just the capital of St. Barths, it’s also a shopping mecca as well, offering international luxury brands such as Hermès, Louis Vuitton, Dior, and Bulgari, home goods, jewelry, personal gifts, and more. Check out La Case Saint Barth, a gourmet rum and food shop; Pop Saint Barth, a locally owned and designed women’s boutique; Ligne St. Barth for natural beauty and self-care products; Clic, a home décor and lifestyle store; Baya St. Barth, a chic concept store; Bijoux de la Mer for unique jewelry creations; and Pati de St. Barth for keepsake clothing. There’s also a Pati de St. Barths shop in the town of St. Jean, which boasts a fair number of boutiques, and at the airport, for it would be a sin to leave the island without something from the original brand of St. Barths since 1989.

Saline Beach, Courtesy: Tourism St. Barts

An abundance of boating and ocean activities await. Private yacht charters, jet-ski rentals, and canoe excursions are available, along with wind surfing, scuba diving, snorkeling, and more. For the uber-adventurous, try a Seabob electric underwater scooter for diving with even more ease and agility. A bevy of unspoiled beaches, coves, and inlets awaits. Saline Beach, on the island’s southern coast, is popular and private, as is Colombier Beach, which is only accessible by hiking. Shell Beach is a natural wonder—the beach is actually made of millions of tiny seashells.

Courtesy: Tourism St. Barts