The May spread in the 2026 Ultimate Sailing Calendar features a striking image by Portuguese photographer Ricardo Pinto, whose work captures both the beauty and intensity of modern racing. Ricardo has a knack for being in exactly the right place when speed, light, and action come together.

There are moments in sailing that defy scale — and then there’s Barcolana.

Held each October in the Gulf of Trieste, the Barcolana is the largest regatta in the world. Thousands of boats converge for a single start, transforming the water into something that feels less like a racecourse and more like a living, shifting tapestry of sails.

The March spread in the Ultimate Sailing Calendar features the legendary yacht Merlin charging downwind beneath the Golden Gate Bridge during the Rolex Big Boat Series in San Francisco.

Photographing the classics is when the wide-angle lens comes out. You want everything in the frame — sweeping sheerlines, polished varnish, full sails, and crews moving in choreography. These yachts are beautifully restored and deeply loved, and the pride in this fleet shows in every detail.

Spray flies and adrenaline surges as the Swan fleet charges upwind through the Bonifacio Channel, where Corsica’s towering limestone cliffs funnel the Mediterranean mistral into one of the most demanding racecourses in Europe.