Special Valentine’s Day Edition! A true story about a first date, a small sailboat, and the unpredictable magic of sailing on San Diego Bay.
The aluminum forest of sailboat masts swayed in the April breeze. For sailors like me, the marina was a church, and today—my first date with Victoria—I needed some divine intervention. I’d skipped the usual restaurant scene to show her a world that has been part of my life since I was born. If she enjoyed sailing, there was hope. If not, there would not be a second date.
I didn’t own a boat, but I could sail. I hoped an afternoon on a rented Catalina 22 would seduce her—or at least impress her. We’d worked together for five years; she was a wedding planner, I was a photographer. Victoria was beautiful, genuine, well-traveled, intelligent, and painfully honest. For her, sailing simply meant boating. Growing up in Coronado, her nautical life was sunset cruises and party boats, where yachting meant the right attire, champagne, and letting others handle the details.
I finished prepping the sailboat and waited. Perched on the dock box, I had a clear view of the concrete pathway that ran from the marina office straight to where the little rental boats were tied.
Jumping to my feet, I waved as she entered the gate. She walked down the dock like a runway model— with confidence and familiarity. The afternoon sun reflected off the yachts, lighting up her oversized sunglasses. Victoria was stunning. The tiny embroidered anchors on her tote bag were a well-thought-out pairing with her halter top sundress and Manolo Blahniks.
Walking the corridor between the pricey yachts with their massive bowsprits, Victoria’s smile beamed as she approached the fleet of little day-sailors. An air of disappointment washed over her face as I proudly introduced her to ‘Bravo’, the 22-foot rental sailboat. Trying her best to look thrilled, she gave me a hug and said, with a playful smirk, “So… this is ‘Bravo,’ Well, OK then!
Holding my shoulder with one hand, she bent her leg back, exposing her inner thigh, and with her other hand, removed the heel strap on her shoe. Then she turned around and removed the other, and I pretended not to notice.
Taking my hand, she dance-stepped on board. I raised the sail and pulled in the mainsheet. We fell into a beam reach and entered San Diego Bay.
The bay was deserted, ours alone on a clear and windy April afternoon. Victoria poured Pinot Grigio and unveiled a charcuterie board. The wind stiffened, stronger than usual for San Diego Bay—where gusts rarely topped 18 knots—but that day, a persistent northwesterly fresh breeze kept us moving. We sailed fast but steady, wind at our backs, eating, drinking, and laughing. We passed under the Coronado Bridge, the cityscape slipping by.
Victoria seemed genuinely happy, even charmed by the humble sailboat. The wind and current had swept us down the bay, and soon, it was time to tack and head back upwind. As I pointed the bow northeast, the strong wind, gusting into our faces, pushed the little boat into a close-hauled tack.
No longer were we enjoying a relaxing downwind cruise, the boat level with the horizon. Now, with the wind gusting, Bravo heeled sharply, tipping past thirty degrees. I sailed like an idiot. Inefficient and dangerous, the little sloop careened across the bay like a Tilt-A-Whirl at a traveling carnival.
Instead of easing the mainsheet or reefing the sails to steady us, I tried to impress Victoria—pushing Bravo to her limit. A sudden gust slammed into the boat, and the leeward gunwale vanished beneath a rush of seawater. The cockpit lurched violently. The charcuterie board went airborne—a constellation of wine, glasses, and olives suspended weightless for a heartbeat.
Victoria, convinced she might soon be swimming in San Diego Bay, scrambled onto the windward side of the boat on her knees. Like a cat above a jacuzzi, she clawed her way to the highest spot she could find, staring down at the water surging through the cockpit.
While Victoria screamed, I was euphoric—drunk on speed and the thrill of wind and water, oblivious to anything but the boat’s movement. The world narrowed to white spray and taut lines until another gust slammed us broadside. Metal snapped: the mainsheet shackle broke free, and the boom whipped across, slamming into the leeward shrouds. The boat jerked upright, and Victoria was hurled onto the swamped cockpit floor. Only then did I see her: sprawled among mangled wine glasses, salty puddles, limp crackers, and cantaloupe, dazed and silent. That wreckage was my handiwork—a disastrous first date.
An hour later, we were back at the dock, the little outboard motor sputtering to a stop. I covered the sails and gave the hull a quick rinse while Victoria helped clean the remnants of appetizers from the deck. She straightened her dress, ran her fingers through her hair, and caught me staring. I was embarrassed and felt like a fool, but I couldn’t look away. I just kept staring. She smiled, looked down at her bare feet, and laughed. “I guess I wore the wrong shoes,” she said. Our eyes met again, and I said, “I’m so sorry”.
She paused, surveying her soaked sundress, then grinned. “Next time, I’m bringing a wetsuit.”
I blinked. “You… want to go again?”
“Oh God, no!” Victoria laughed. “If you want me to sail with you again, you’re gonna need a bigger boat—and not sail like a lunatic!”
I did get a bigger boat. And, with a few exceptions, stopped sailing like a lunatic. Over the last 18 years, we’ve sailed thousands of miles since that chaotic afternoon on Bravo, through calm seas and storms far worse than anything San Diego Bay could conjure. We live this life together—trimming sails, reading charts, and taking turns at the helm. The boat grew bigger, but what we’ve built together—trust, partnership, a shared language of wind and water—that’s the vessel that’s carried us farthest. Because in the end, sailing and life are the same: you can’t control the wind, only how you set your sails. And she still reminds me, whenever I push too hard into the wind, to ease the sheet and remember the day charcuterie went flying.
Today, Sail Riviera San Diego offers private luxury sailing experiences on San Diego Bay—now with bigger boats and seasoned captains. If you’re searching for one of the most romantic things to do in San Diego this Valentine’s Day (or any day of the year), contact us to book your private luxury sailing experience.