When Elisabeth Novak and Taylor Cain first met at a countryside dinner party in Sonoma, California, they were each captivated. “I was immediately welcomed by Taylor’s gentlemanly nature, intrigued by his wit and ease of conversation, and impressed by his ability to help with the dishes,” Elisabeth smiles.

Years later, Taylor surprised Elisabeth with a proposal on a holiday ski trip in Japan. “I had the ring picked out without her input – she’s classically beautiful, so I just went classic,” he says of the sparkler created by Elisabeth’s aunt, a jeweler. “He proposed on Christmas Eve after an epic powder day in the serenity of a private onsen,” remembers the bride.

The San Francisco-based couple soon began planning a destination wedding in Italy. “We love food and wine, and we wanted to have a wedding that could showcase the beauty and bounty of wine country,” shares Elisabeth. “Having an Italian family myself and a mutual love of travel, the Val d’Orcia region of Tuscany was the perfect fit.” They even rented out their venue for a week in order to spend as much time as possible with their 75 guests, also hosting a welcome dinner the evening before and a poolside brunch the following day.

Their early June nuptials were blessed with warm days and cool nights. “We felt very lucky to have flowers in full bloom and the countryside a deep green,” the groom shares, fitting the vision perfectly. “I wanted to complement the essence of Val d’Orcia and be one with the beauty of the landscape,” the bride explains of the palette. “Timeless Tuscan greens became the centerpiece of our design, with an emphasis on natural, yet elegant textures.”

Friends and family gathered on the lawn overlooking the rolling hills of Tuscany as Elisabeth walked down the aisle in Claire Pettibone’s “Peony” gown, featuring embroidered dusty rose peonies entwined with sage green stems, paired with the designer’s floral-embellished “Primavera” veil for the ceremony and detachable “Les Fleurs” cape sleeves for the reception.

The groom’s father served as officiant. “He is a great husband, phenomenal father, and a genuine role model to his kids, [so] having him take that role was really special,” shares Taylor. Elisabeth adds, “He authored and orated an absolutely heartfelt and charming ceremony. There was not a dry eye in sight!”

“I will always remember being announced into the courtyard for dinner as Mr. and Dr. Cain.”

A dinner beneath the stars followed in the courtyard, where two wooden tables were dressed with flowing linens and colorful arrangements of peonies. “I will always remember being announced into the courtyard for dinner as Mr. and Dr. Cain to the pointed song choice of Enya’s ‘Orinoco Flow,’ which was met with boundless smiles and cheer from our loving family and friends,” says the bride.

As a formal welcome dinner was hosted the night before, the couple wanted the reception to feel more relaxed and celebratory. Guests enjoyed a variety of seasonal wood-fired pizzas and endless bowls of fresh pasta, paired with Brunello di Montalcino “hailing from just over the hills, to the pleasure of many of the wine lovers in the crowd,” confirms Elisabeth. “It was such a hit!”

Music carried the energy of the day from start to finish. A string quintet complete with a harpist, much to the delight of the bride, performed for the ceremony, followed by jazz guitarists at the reception, a strolling band during dinner, and a DJ who kept the celebration going until 2AM. “The combination of several entertainers enabled us to keep an appropriate tempo for each aspect of the evening as it unfolded,” notes Taylor.

For a memorable interactive moment, the newlyweds assembled a traditional Italian millefoglie wedding cake. “It was such an unexpectedly fun part of the evening as guests gathered around to watch me and Taylor construct the crowning layers of Chantilly cream and berries, which turned out to be one of the most delicious wedding ‘cakes’ I’ve ever had!” shares Elisabeth.

Filled with love and memories, the newlyweds extended their European sojourn with a honeymoon exploring Tuscany and sailing in the French Riviera, savoring “all its summer glory” and the joy of a wedding celebration that perfectly reflected their shared love of adventure, family and friends, and classic beauty.

This real wedding was originally published in the Winter 2026 issue of Inside Weddings magazine. 

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