The Back Story

It always fascinates me how couples meet—a dinner party, arranged by a nosey aunt. A chance meeting with friends at a bar, or perhaps she just swiped right, and the rest was history.

Clinton, a young man from Arizona, first saw Kaleen (his future wife) in 2017 on a beach in San Diego, precisely seven years ago this month. Like a scene from a 1960s beach party movie, Clint tossed a football near Kaleen and her friends, thus giving him a chance to say, “Hi, I’m Clint.” They spoke briefly, but it wasn’t until four years later, on a dating app, they reconnected.

Black and white image of a couple admiring an engagement ring.

Marriage proposals on Riviera are always fun and exciting. Despite the chilly February afternoon, we found a clear weather window for a young man to drop to his knee and ask, “Will you marry me?” on the yacht’s bow in the middle of San Diego Bay.

Winter sailing in San Diego can be a blast! Albeit unpredictable. Kudos to Captain Dan Sullivan for his mad sailing skills as the weather turned from mellow and calm to wild and windy in less than 10 minutes.

THE 4:20 PLAN (*Glossary of Nautical Terms Below)

Clinton, our “groom-to-be,” was like all young men about to propose. Focused and determined to impress and delight his soon-to-be fiancee, Clint had arranged for their close friend and professional photographer, Jenny, to hide in the forward cabin below deck, then pop up at precisely 4:20 PM and shoot the proposal and hopefully the acceptance.

The afternoon’s sail started well. They cast off, and a mild breeze glided Riviera into the harbor. As they sipped their tangerine margaritas, Kaleen, had no clue he was about to propose.

 By 4:00 PM, as Riviera headed toward Point Loma, the wind picked up to 12 knots*, and by 4:15, under full sail and on a beam reach*, the apparent wind* speed was over 25 knots.

Realizing that a proposal on the foredeck* while the boat was heeling* at a 30-degree angle was not ideal, Captain Dan quickly furled* in the jib* and executed a controlled gybe*, turning downwind, and then reefed* the mainsail. Dan’s fast thinking stabilized Riviera, thus setting the stage for the perfect proposal.


Clint glanced at his watch. The time was 4:20. Nervous and a bit wound up, Clint did his best to nonchalantly suggest to  Kaleen that they move to the foredeck.

 The photographer, Jenny, emerged from hiding and made her way topside. As Clint dropped to his knee, Kaleen, experiencing “tunnel vision,” was oblivious that Jenny was standing on the deck shooting the action. The ring now appeared, as did tears of joy and a resounding YES!

Finally, Kaleen’s jaw dropped as she realized that her dear friend Jenny was also on board with her camera, documenting everything.

Here are a few photos, compliments of

Man holding an engagement ring, proposing to his girlfriend on the deck of the Riviera sailboat
Couple leaning in for a kiss after getting engaged
Couple kissing after getting engaged on the Riviera sailboat, with the San Diego Bay in the background
Couple posing together on the deck of the Riviera sailboat after getting engaged


Apparent wind–  the wind you feel when you’re moving, compared to “true wind.” True wind is the actual wind that is blowing. 

Beam reach – a point of sail where the boat is sailing at a right angle to the apparent wind. 

Foredeck – the forward part of a boat’s main deck

Furl – to roll up and neatly secure a sail.

Gybing – turning the boat so that the stern (back of the boat) crosses the wind, changing direction

Heel – the lean of the boat caused by the wind’s action on the sails

Jib – a foresail. On a sailboat, this is the forwardmost sail.

Knot – a nautical mile (equivalent to 1.15 miles ). A 20-knot wind is equal to 23 mph. 

Reef – to reduce the area of a sail.

A big thank you to Capt. Dan, for knowing how to “dance” with the wind and sea, and our Steward, Michael, for always going above and beyond with unparalleled service.

From all of us on Riviera, we are committed to creating the best possible sailing experience every time we cast off. Whether you’re planning to propose marriage or simply want a memorable evening on San Diego Bay, we’re here for you.

Fair Winds & Following Seas
Paul & Victoria

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