ABC7 News was at the Port of Oakland as David Walton set sail.
He's a resident at The Point at Rockridge, an Integral Senior Living Community.
It has a "Livin the Dream" program that allows residents to experience a day in their past or cross something new off their bucket list.
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Walton had spent many years sailing around Greece, so he was excited about the opportunity to get back on the water.
"It's been a lovely, lovely day," he said. "And I woke up this morning having no idea this was going to happen, so - YEAH!"
He took a three-hour boat ride with a family friend and a neighbor.
They sailed near the Bay Bridge and along the San Francisco skyline.