Cyclades Cup returns for its third edition in Antiparos, Greece
by Pilot Room 29 Jan 01:21 PST
10–13 June 2026

Cyclades Cup © Kurt Arrigo
In the heart of the Aegean, where light, wind and open horizons define the rhythm of sailing, the Cyclades Cup will return for its third edition from 10-13 June 2026 in Antiparos, Greece.
Conceived as an invitation-only, owner-led regatta, the event brings together a carefully selected community of yachts, owners and crews for three days of racing and shared life on the island, having carved out a distinctive place within the Greek sailing landscape.
Created by owners for owners, the Cyclades Cup was born from a desire to offer something different: a regatta where competition exists in harmony with experience. Racing remains central, but it is never isolated from the wider rhythm of life at sea and ashore. Owners are directly involved, families and guests are present, and crews are part of the same shared moments — on the water and on the island.
Designed to remain intimate and carefully curated, the Cyclades Cup brings together a limited number of participants who share a common approach to sailing and life on board. The experience is shaped by balance rather than scale: time on the water is matched by moments on shore, and competition naturally blends with social life, creating a rhythm that feels unforced and genuine.
Racing takes place in the waters surrounding Antiparos and the neighbouring Cyclades, across one of the most evocative sailing areas of the Aegean. Courses follow the natural geography of the archipelago, moving between open stretches and sheltered passages, allowing the landscape itself to shape the experience on the water.
What truly defines the Cyclades Cup is its sense of continuity. Owners and crews return year after year, drawn not only by the sailing, but by the shared rhythm, familiar faces and the quiet certainty of belonging to a community that recognises itself in the event's values. Over time, the regatta has become a ritual - remembered as much for the moments between races as for the competition itself.
More than a sporting event, the Cyclades Cup offers a refined yet relaxed way of experiencing a regatta. Simple logistics, an easy-going pace and the freedom to combine racing with cruising through the Greek islands allow the week to unfold as a complete sailing experience. Returning for its third edition, the Cyclades Cup continues to affirm its identity as a boutique regatta shaped around people rather than spectacle.
www.cyclades-cup.com