Sailing, Poker & Gourmet Delights: A Weekend Adventure with Friends

Ever since the world came to a grinding halt in 2020, our ragtag group of friends has gathered online every Friday for poker (and occasional trash talk). But when in-person life returned, we decided to up the ante: no more “same old, same old.” Couple of years we hit Las Vegas; this year, we traded neon lights for city lights on the San Francisco Bay. The plan? A weekend sailing escapade aboard two boats—Zosca and Typon (a gorgeous Swan 47 S&S)—with enough food, wine, and poker games to make even the most glamorous Vegas buffet raise a white flag in surrender.

Friday: And So It Begins…

Picture this: Redwood City Marina and Westpoint Harbor, two shiny (well, mostly shiny) sailboats, a pile of luggage, and a bunch of excited people running around like kids on a treasure hunt. We did a quick skipper’s briefing—“No, you don’t need a life jacket for your poker chips!”—and loaded our gear, snacks, and suspiciously large cooler boxes onto Zosca and Typon.

After a short (but necessary) skipper’s briefing, we set off, each boat eyeing the other in a not-so-secret race. Naturally, as soon as we left the dock, Ilpo (our resident GT keeper) declared it was “Gin & Tonic O’Clock.”, like he does every Friday at 5 pm.

On the way, we fished a random floating drum (yes, the musical instrument kind) out of the bay. We’re not sure if it was a sign from Poseidon or just a very confused piece of cargo, but it’s now the official symbol of our journey. “I’m never going to forget pulling a random drum out of San Francisco Bay,” laughed Peter, who then gave it a few taps as a victory salute. After rescuing the drum, we sailed past the stunning San Francisco skyline at twilight—if you ever wanted a perfect postcard moment, that was it.

By the time we reached Ayola Cove on Angel Island (about four hours later), our stomachs were performing their own symphony. Cue Matti, who had whipped up a chef’s kiss dinner aboard Zosca. Then it was on to our first cash poker game of the weekend. Let’s just say Jani should start wearing a cowboy hat because he cleaned out everyone’s pockets like a seasoned cardsharp.

Saturday: Sea Breezes, Spinnakers & The Big Tourney

We woke up to the gentle bobbing of the boats—much better than any alarm clock. Over on Zosca, Matti was already cooking up a next-level breakfast, starting with caviar and high-end vodka. Because why not? We were determined to spend this weekend as pampered as possible.

Golden Gate Sailing & Island Exploring

After breakfast, several of us hopped onto Typon to sail out toward the Golden Gate Bridge. The highlight? Hoisting a spinnaker on the return, which always feels a bit like flying a giant, overpriced kite. Despite a few comedic tangles, we managed to execute it pretty smoothly—shoutout to the volunteer crew who only occasionally pulled on the wrong ropes.

Back on Zosca, Matti prepared for the evening’s feast. Matti, Jani, and Jouni hiked up Angel Island for a quick dose of panoramic views. “Standing atop Angel Island, listening to the birds and the ocean breeze—that’s how you recharge,” Matti commented later, grateful for his own short hike break.

Poker Showdown on Zosca

Saturday night meant the live poker tournament, which started at two tables—one indoors, one out on the deck—then merged into a single final table. The tension? Palpable. The stakes? Mostly bragging rights (and some folks’ pride). In a nail-biter finish, Ilpo emerged victorious, with Mika coming in second.
As for Jani, who dominated the night before? Well, let’s just say Lady Luck decided to take a nap. But that’s poker!

Sunday: Champagne Handoffs & Fond Farewells

When Sunday rolled around, we savored our last morning afloat—a frittata and gravlax on freshly baked garlic bread (because obviously Matti wasn’t done impressing us yet). The day’s sail back to Redwood City was calm, giving us just enough thrill to attempt our most daring maneuver of the weekend: a mid-bay champagne handoff. We got Zosca and Typon so close you could pass a champagne bottle from one boat to the other without losing a drop. “Out-of-this-world food mixed with the best of sailing,” commented Peter, helping himself to a flute of bubbly.

As late afternoon arrived, so did we—back at Redwood City Marina. The final chore: cleaning up the boats and sorting out whose socks belonged to whom. Exhausted but grinning ear to ear, we ended the weekend at the Sequoia Yacht Club, toasting by the fireplace. “Lying on the deck under the Golden Gate felt like a movie scene,” Mikko reminisced between sips. “I can’t believe it’s still November.”

Sure, some of us left a little lighter in the wallet (thanks to the poker sharks among us), but we all gained a haul of stories to carry us through the winter.

Fair Winds and Full Hearts

From rescuing a random drum in the bay to hosting a champagne-handoff spectacle, this weekend had enough excitement (and gourmet indulgence) for a lifetime. Whether it was Ilpo taking home the poker trophy, Matti dazzling us with flavors, or Mikko daydreaming under the Golden Gate, each one of us found a new reason to love sailing—and maybe an old reason to keep practicing our poker faces.

Until the next adventure, may your sails be steady, your wine glasses ever-full, and your poker hands just lucky enough to keep things interesting. Cheers to another year of friends, fun, and the occasional spin of the spinnaker!