Classic regatta calendar 2027

Racing the classics

Every season the great classic yachts gather to race: gaff cutters and schooners from the turn of the last century, the elegant metre boats and yawls of the 1930s, and the finest of their modern descendants. The racing is serious, the setting spectacular, and the dock in the evening is the best place in the world to see these yachts side by side.

This calendar lists the main classic regattas of 2027. Where the organisers have not yet confirmed the dates, we show when the regatta is usually held, and we update the calendar as dates are announced.

The 2027 calendar

How the season fits together

For fourteen years the Panerai Classic Yachts Challenge linked the great classic regattas into one circuit, until Panerai ended its sponsorship at the end of 2018. The Mediterranean regattas now count towards two championships. The CIM Championship ranks yachts that race at four or more events in at least two countries, and the Vintage Classic Yacht Club’s Mediterranean Champions Cup, set up in 2022 to fill the gap Panerai left, runs from one Saint-Tropez to the next Cannes. Spain has its own series, the Trofeo Clásicos Mare Nostrum; the UK has the West Country Classics; and New England has the Classic Yacht Owners Association’s Classic Yacht Challenge.

The Fife Regatta, which gathers William Fife’s yachts on the Clyde every few years, last sailed in June 2026, so it is not on the 2027 calendar.

Racing on a charter yacht

• The yacht holds the rating. Each regatta names the certificate it requires: CIM for the Mediterranean classic classes, CRF in the Caribbean and New England, IRC at British Classic Week. A yacht that races regularly will hold the right one.
• Book early. Regatta weeks are the busiest dates of a yacht’s year, and regatta rates are usually higher than cruising rates. The superyacht events close entries months ahead: Superyacht Challenge Antigua takes applications until 1 December 2026.
• Racing crew. Big classics race with extra professional crew aboard, and guests can take as active or as relaxed a part as they like.
• Paperwork in France. At French regattas, crew without a French sailing licence need proof of membership of their national sailing authority, such as the RYA, third-party insurance and a recent medical certificate.
• Taking part without racing. Some events welcome yachts that would rather watch: Illes Balears Clàssics has a class for them, and the Semaine du Golfe is a festival of flotillas, not a race.

Yachts to charter for a regatta

These yachts are chartered for classic regattas as well as cruising. Tell us which regatta you have in mind and we will check which are entered and available, including yachts not listed here. See also our regatta racing yachts.