A Season of Culture, Celebration and Connection at Four Seasons Resort and Residences Anguilla

As summer arrives in Anguilla, the island comes into its most vibrant season; when culture, celebration, and community take centre stage. At Four Seasons Resort and Residences Anguilla, this dynamic energy is reflected in a thoughtfully curated calendar of experiences that celebrate the island’s rich heritage. From iconic boat races to lively festivals and local market experiences, this is a time when Anguilla’s spirit is on full display, offering an unmatched blend of authenticity, tradition, and effortless island luxury. In addition to the resort’s summer programming, visitors and locals alike are invited to immerse themselves in a season that showcases what makes Anguilla truly special.

“Summer is one of the most exciting times to experience Anguilla,” says Diego Stembert, General Manager. “From long-standing traditions such as boat racing to the energy of festival season, this is a time when community and culture come together in a greatly meaningful way. We are proud to support and celebrate the people, events, and experiences that make Anguilla so special.”

Kicking off the season on May 31, 2026 is the Local Market Experience honouring Anguilla Day with an afternoon of local flavour and craftsmanship. Held on Sunset Lawn from 4:00 to 7:00 pm, the event features artisanal goods, vibrant flavours, and curated offerings from local vendors. Visitors can discover fresh cuisine, refreshing beverages, and island-made treasures that come together to showcase the heart of the community.

On June 1, 2026, guests are invited to experience one of the island’s most treasured traditions during a Boat Racing Watch Party, coinciding with the A Class Anguilla Day Premier’s Cup - an iconic around-the-island race. Recognized as Anguilla’s national sport, boat racing is deeply woven into the island’s cultural identity, bringing communities together in spirited competition and pride. As part of this commitment to local tradition, Four Seasons Resort Anguilla is sponsoring the Bush Boyz racing boat this season. The watch party offers a chance to engage in this beloved pastime in a lively, communal setting, with races continuing throughout June, July, and August as a cornerstone of the summer calendar.

The excitement continues throughout the season, culminating at the season closing Boat Racing Watch Party on August 6, 2026, set against a dynamic beachfront backdrop for the A Class race at Meads Bay. This celebration promises to capture the energy and passion surrounding the sport while marking the end of the season in unforgettable style.

The island will come alive with Anguilla Summer Festival from July 10 through August 9, 2026, a cornerstone of the cultural calendar featuring parades, music, and vibrant non-stop festivities. This year, support extends to the celebration through sponsorship of the Players Troup. In 2026, Players Troup celebrates 15 years, with more than 200 vibrant players, including many Four Seasons Resort Anguilla employees, expected to participate in mas.

Bringing the spirit of the festival on property, guests will also have the opportunity to engage with an immersive on-property experience highlighting the artistry and cultural significance of Summer Fest, offering insight into traditional mas, costume design, and the history behind this beloved island celebration.

The summer season in Anguilla invites guests to discover a destination where warmth extends beyond the weather. Together, these initiatives reflect a continued dedication to celebrating Anguilla’s culture, supporting local traditions, and investing in the community that makes the island so unique. The season offers opportunities to make the most out of every moment with a special Discover Anguilla offer - inviting guests to stay longer, indulge more, and savour the season.

To plan a summer escape to the Caribbean at Four Seasons Resort and Residences Anguilla, visit the resort online or email reservations.anguilla@fourseasons.com.