Sailing With Bogie

Sunday on the Bay with the Kaplans—and their very famous schooner.

There is hardly any fiberglass in The Santana. Its 55-foot deck is teak, its two masts are hollow spruce, its stanchions are bronze and the rest of the schooner is made of mahogany planks. Below deck, the liquor-cabinet doors are leaded glass, and a hidden drawer in the aft cabin reveals a velvet-lined jewelry box once used by June Allyson. On deck, just in front of the helm, the round mahogany drink holder that secures up to 10 beverages—plus one big bowl of nuts— was Humphrey Bogart's idea. Bogie bought the boat in 1945 and, over the next decade or so, sailed the coast of Southern California with his wife, Lauren Bacall, and such A-listers as Frank Sinatra. In its 73-year history, it's also been owned by George Brent and Ray Milland. Calling The Santana a sailboat is akin to calling Catherine Deneuve a female.

So it's fitting that Paul Kaplan was the one who happened to spy The Santana sitting in the SF Marina in 1997. Then 43, Kaplan had been sailing since the age of 10, when he was at Lake Merced one day and a teenage boy offered him a ride on his 13-foot OK Dinghy. Kaplan, who grew up in Balboa Terrace, learned to sail before he learned to drive a car; as a 12-year-old, he'd catch a ride from his pediatrician mom, Peg, to the Golden Gate Bridge toll plaza, then hop a bus to the SF Yacht Club in Belvedere, where he enrolled in the junior sailing program. Though he initially planned to become a marine biologist, he changed his mind at 17, while on a sailboat headed to the Galapagos. On board was Bernie Goldhirsh, the founder of Sail and, later, Inc. magazines. One night at 2 a.m. while out at sea, Goldhirsh asked Kaplan, "Do you really want to live from grant to grant your entire life, studying plankton, or do you want to make a living boating?" At 19, Kaplan borrowed money from his parents to buy a quarter-share of a yacht brokerage in Fort Mason. Six months later, he had paid them back, and several years later had bought out the other three owners. Kaplan and his wife of 32 years, Chrissy, still own the brokerage as well as the Bay's largest full-service boatyard, in Point Richmond.



Though The Santana had sunk and been refloated at the time he first saw it, Kaplan recognized its past glory and future potential. As he told Chrissy then, "When I fell in love with sailing, this is what I had in mind." The Kaplans bought The Santana 10 days later and spent the next year restoring it. It is Kaplan's 35th boat. "Paul knows every boat in this bay and has won almost every race on it," says his mom as she takes the helm of The Santana on a recent Sunday afternoon, surrounded by Paul's dad, Bill; the Kaplans' two grown daughters, Sarah and Erica; and a host of family friends. "These are things he won't tell you." Kaplan doesn't need to toot his own horn—mention his name to anyone in the local boating community and you'll hear declarations of affection and respect. Sailing well is one thing, but sailing well here is another. Because of its shape and the way the pressure system over our relatively warm landmass pulls the colder Pacific water in through the Golden Gate, the Bay is known worldwide for its reliable, hardy westerly winds and choppy currents. "Every day the water, wind and current are different," Kaplan says. He navigates this complex topography effortlessly, correctly estimating the number of seconds it will take for the wind to kick up and maneuvering the boat between two huge cargo ships headed for the Gate.

"Sailing is not a direct route to anywhere," says Kaplan. "It's too slow for some people." As he leans back, sitting on his beloved schooner surrounded by family and friends, the choice between the direct and the indirect route suddenly seems like a no-brainer.

Click here to see exclusive video.

There is hardly any fiberglass in The Santana. Its 55-foot deck is teak, its two masts are hollow spruce, its stanchions are bronze and the rest of the schooner is made of mahogany planks. Below deck, the liquor-cabinet doors are leaded glass, and a hidden drawer in the aft cabin reveals a velvet-lined jewelry box once used by June Allyson. On deck, just in front of the helm, the round mahogany drink holder that secures up to 10 beverages—plus one big bowl of nuts— was Humphrey Bogart's idea. Bogie bought the boat in 1945 and, over the next decade or so, sailed the coast of Southern California with his wife, Lauren Bacall, and such A-listers as Frank Sinatra. In its 73-year history, it's also been owned by George Brent and Ray Milland. Calling The Santana a sailboat is akin to calling Catherine Deneuve a female.

So it's fitting that Paul Kaplan was the one who happened to spy The Santana sitting in the SF Marina in 1997. Then 43, Kaplan had been sailing since the age of 10, when he was at Lake Merced one day and a teenage boy offered him a ride on his 13-foot OK Dinghy. Kaplan, who grew up in Balboa Terrace, learned to sail before he learned to drive a car; as a 12-year-old, he'd catch a ride from his pediatrician mom, Peg, to the Golden Gate Bridge toll plaza, then hop a bus to the SF Yacht Club in Belvedere, where he enrolled in the junior sailing program. Though he initially planned to become a marine biologist, he changed his mind at 17, while on a sailboat headed to the Galapagos. On board was Bernie Goldhirsh, the founder of Sail and, later, Inc. magazines. One night at 2 a.m. while out at sea, Goldhirsh asked Kaplan, "Do you really want to live from grant to grant your entire life, studying plankton, or do you want to make a living boating?" At 19, Kaplan borrowed money from his parents to buy a quarter-share of a yacht brokerage in Fort Mason. Six months later, he had paid them back, and several years later had bought out the other three owners. Kaplan and his wife of 32 years, Chrissy, still own the brokerage as well as the Bay's largest full-service boatyard, in Point Richmond.



Though The Santana had sunk and been refloated at the time he first saw it, Kaplan recognized its past glory and future potential. As he told Chrissy then, "When I fell in love with sailing, this is what I had in mind." The Kaplans bought The Santana 10 days later and spent the next year restoring it. It is Kaplan's 35th boat. "Paul knows every boat in this bay and has won almost every race on it," says his mom as she takes the helm of The Santana on a recent Sunday afternoon, surrounded by Paul's dad, Bill; the Kaplans' two grown daughters, Sarah and Erica; and a host of family friends. "These are things he won't tell you." Kaplan doesn't need to toot his own horn—mention his name to anyone in the local boating community and you'll hear declarations of affection and respect. Sailing well is one thing, but sailing well here is another. Because of its shape and the way the pressure system over our relatively warm landmass pulls the colder Pacific water in through the Golden Gate, the Bay is known worldwide for its reliable, hardy westerly winds and choppy currents. "Every day the water, wind and current are different," Kaplan says. He navigates this complex topography effortlessly, correctly estimating the number of seconds it will take for the wind to kick up and maneuvering the boat between two huge cargo ships headed for the Gate.

"Sailing is not a direct route to anywhere," says Kaplan. "It's too slow for some people." As he leans back, sitting on his beloved schooner surrounded by family and friends, the choice between the direct and the indirect route suddenly seems like a no-brainer.

Click here to see exclusive video.

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