A season full of culture, celebration and connection at Four Seasons Resort and Residences Anguilla | News
When summer arrives in Anguilla, the island experiences its most vibrant season; when culture, celebration and community are central. At Four Seasons Resort and Residences Anguilla, this dynamic energy is reflected in a carefully curated calendar of experiences that celebrate the island’s rich heritage. From iconic boat races to vibrant festivals and local market experiences, this is a time when Anguilla’s spirit is on full display, offering an unparalleled 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 age-old traditions like boat racing to the energy of festival season, this is a time when community and culture come together in a deeply meaningful way. We are proud to support and celebrate the people, events and experiences that make Anguilla so special.”
The season kicks off on May 31, 2026 with the Local Market Experience in honor of Anguilla Day with an afternoon full of local flavor and craftsmanship. The event will be held on Sunset Lawn from 4:00 PM to 7:00 PM and will feature artisanal products, vibrant flavors and curated offerings from local vendors. Visitors can discover fresh cuisine, refreshing drinks 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 cherished traditions at a Boat Racing Watch Party, coinciding with the A Class Anguilla Day Premier’s Cup – an iconic race around the island. Recognized as the national sport of Anguilla, 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 race boat this season. The watch party offers the chance to take part in this much-loved pastime in a lively, communal environment, with races running through June, July and August as a cornerstone of the summer calendar.
The excitement will continue all season long, culminating in the season-ending Boat Racing Watch Party on August 6, 2026, against a dynamic beachside 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 comes alive from July 10 to August 9, 2026 with the Anguilla Summer Festival, a cornerstone of the cultural calendar with parades, music and lively non-stop festivities. This year, support extends to the celebration through sponsorship of the Players Troup. In 2026, Players Troup will celebrate 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 to the grounds, guests will also have the opportunity to take part in an immersive on-site experience, highlighting the artistic and cultural significance of Summer Fest and providing 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 just the weather. Together, these initiatives reflect an ongoing commitment to celebrating Anguilla culture, supporting local traditions and investing in the community that makes the island so unique. The season offers opportunities to make the most of every moment with a special Discover Anguilla offer, inviting guests to stay longer, enjoy more and enjoy the season.
To plan a summer vacation to the Caribbean at Four Seasons Resort and Residences Anguilla, visit the resort online or email [email protected].
