It’s always both great fun and a rare photographic opportunity to experience a regatta from aboard one of the race boats themselves. The 2026 Master Mariners Regatta, photographed from the deck of the 51-foot Alden ketch Pegasus, was no exception.

The Master Mariners Regatta is one of the Bay Area’s most visually spectacular sailing events, bringing together dozens of classic wooden yachts, vintage racers, and traditional sailboats for a day of spirited competition on San Francisco Bay. With the city skyline, Alcatraz, Angel Island, and the Golden Gate often appearing in the background, it’s also a dream setting for marine photography.

This year’s race delivered the kind of conditions the event is famous for — strong afternoon winds pushed into the upper 20-knot range, creating dramatic spray, heavily reefed sails, and thrilling action across the fleet.

The 51-foot Alden ketch Pegasus, is itself a beautiful example of classic yacht design, and being aboard during the race offered a unique perspective of one of the Bay’s most colorful annual sailing events.

View the full photo gallery here: Master Mariners Regatta Gallery

Pegasus is also used by Pegasus Voyages, a Bay Area nonprofit organization that takes local school groups and youth organizations out on San Francisco Bay for hands-on sailing and maritime education experiences. Their programs help connect young people with the Bay through seamanship, teamwork, navigation, and environmental awareness.

The Master Mariners Regatta remains one of the great visual traditions of San Francisco Bay — a living celebration of classic boats, seamanship, and the enduring culture of sailing on the Bay.