Boomer Babe Goes Sailing With Captain Bill

sailingFRIDAY FUNNIES: ‘SAILING LESSONS, that’s what I got you for your birthday”, Blue Eyes proudly declares. His face is so lit up I feel this is akin to getting La Perla lingerie for my birthday, a gift not without attached. But I bite, the idea of captaining an elegant 37′ Beneteau through the Caribbean Isles does kinda float my boat.

Already visualizing my crisp new white and navy sailor wardrobe complete with assorted striped bateau neck jerseys I’m definitely warming up to the idea of sailing. I’m thinking matte red lipstick. This could mean an entirely new fashion horizon for me.

“When do we fly out, Baby?” I inquire, wondering what out first tropical port of call will be. I’m already mentally packing my best bikinis for this sailing expedition.

My head now deep inside my frightfully large closet, rooting for that cute little white sailor hat I vaguely recall purchasing, I hear Blue Eyes’s muffled voice explaining “Um… I booked our lessons in San Francisco Bay, so we’ll need to get some cold weather gear.”

“What, the Bay!?” I shriek in disbelief. But the water’s freezing there, my bikini will look terrible over a 8mm wetsuit! What happened to sailing in the Bahamas?”

sailingGrudgingly I agree that it’s best to train locally so we can sashay about with the greatest of ease when we do hit the isles for some smooth sailing. Off to West Marine we go to explore the biggest collection of unflattering, shapeless jackets I have ever seen. Don’t get me started on the measly women’s selection. I mean seriously, Donna Karan’s GOT to get herself in here.

Deciding to embrace the fact that we are actually clothes shopping together, a rare occasion, I have Les, our unsuspecting salesman breathlessly running to and fro form the stock room for sizes.

Things take a turn for the worse when it becomes apparent I will need to purchase the most hideous pair or stiffly insulated overalls I have ever seen in my life. These puppies have a drop seat for the ladies to facilitate easy ‘head’ access. I’m serious. Les tells me that if I look like I’m wearing oversize adult diapers I’ll know I have the right fit.

This is a terrible blow to my ego.

Hundreds of unfashionable dollars later we are off to meet Bill, our San Francisco sailing guru. Capt Bill is a white-bearded, Tai Chi practicing ex-marine, ex corporate dude who’s sailed every imaginable ocean and I can’t help but admire his patience.  Lord knows we are trying it as we damn near get ourselves crushed by one of the Americas Cup boats racing the Bay in mid tack.

Today happens to be the Rolex Cup Race.

Our first two day lesson turns out to be a blast, I can now tack, jibe and willfully boss people around on the boat when I’m at the tiller. And my crew must to obey, what fun! So easy to get carried away.  Down girl…

One facial sunburn later I order a waxed cotton Watership hat just like Bill’s, hoping I’ll appear more experienced wearing it. It doesn’t look too bad either, I can playfully flip the brim up to give it a more feminine touch.

Our next two-day set of sailing lessons involves both a written and hands-on test which has us cramming till the wee hours. Luckily, angels are watching over me and I pass with flying sails, 96%. God bless multiple choice.

Now for the ‘parking a large sailboat in a rickety-ass little dock with expensive boats all around you’ test. The tide current makes maneuvering rather tricky. Oh, and the Bay is jam-packed with boat traffic because Blue Angel, Mig and Raptor jets are roaring overhead practicing stunts for tomorrow’s show. On the water no one’s watching the other guy.

I know, the term ‘Blue Angel’ has a totally different meaning for me too.

Incredulously I pass the parking test too, even get cheered on by a weather-beaten old salt reclining on his docked sailboat. He’s watching me park repeatedly. Apparently I rate better than a Raptor and I KNOW it’s not the sexy overalls.

sailingFor fun Capt Bill directs me to sail us to Sausalito and miraculously I am able to oblige. The fighter jets are swooping so low we can actually see the pilots’ faces. Their sonic booms thunder in my chest and, whooping excitedly with rock concert volume I feel goosebumps pressing against my many layers. Bill looks at me with a twinkle, guess he didn’t know this Boomer Babe was such a hootin’ tomboy at heart.

Suddenly the coast guard is upon us, our lollygagging has me inadvertently steering us into the dangerous, heavily guarded ‘boats verboten’ air show zone. I’m on the verge of getting us all arrested when Bill deftly snatches the tiller from me and gets us the hell outta there. Tee-hee… this bay sailing ain’t so bad after all.

I’m looking forward to next month’s installment of Bay with Capt Bill. I’m so going to kick butt in my drop seat pants.

Aarrrr matey.


Esmée SJ