Stylish Rooftop Wedding at the Hotel Californian

Diana and Leland’s wedding at the HOTEL CALIFORNIAN in Santa Barbara was a joyful blend of Mediterranean charm, timeless style, and deeply personal touches — all beautifully captured by photographer ANYA KERNES. With expert planning by SWEET BLOSSOM WEDDINGS, every detail reflected the couple’s desire for a wedding day that felt effortlessly chic, relaxed, and most of all, authentic to them.

The couple’s love story began in Las Vegas, where Diana was celebrating a friend’s mom’s 50th birthday and Leland was attending a bachelor party. Years later, Leland proposed on the beach at Coronado Island in San Diego, not far from their home. The proposal began with a red herring — a “Marry Me” sign that Diana assumed was for her — before Leland dropped to one knee further down the beach with a hidden photographer capturing the moment. Friends and family were waiting at a bar afterward, adding a heartfelt surprise to an already emotional day.

From the very beginning of their wedding planning, Diana wanted to lean into the Mediterranean aesthetic of the HOTEL CALIFORNIAN, mixing citrus and florals for a fresh, elegant vibe. HAUTE BLOSSOM FLORAL brought this vision to life with simple white blooms, buckets of lemons, and a vibrant bougainvillea chuppah that added a bright splash of color to the ceremony. The hotel’s architecture set the tone for a day that was stylish and sun-soaked — and uniquely theirs.

Stationery was especially meaningful to Diana and her mother, who worked with LAURA HOOPER DESIGN HOUSE to create a bespoke crest used throughout the celebration. One of the most cherished pieces was the welcome bag itinerary, which included photos and love stories from both their parents and grandparents — a subtle but emotional tribute to their family legacies.

Diana got ready with her bridal party in a suite at the HOTEL CALIFORNIAN, sipping spritzes and skipping the traditional matching pajamas in favor of the hotel’s robes. The couple opted for a first look to ease nerves and capture portraits before the ceremony. Leland immediately made Diana laugh by pointing out she had something in her teeth — a sweet, grounding moment that reflected the playful intimacy between them.

For fashion, Diana knew exactly what she wanted. A year before the engagement, she tried on a YSL tuxedo in Paris and bought it on the spot for a future rehearsal dinner — a bold, fashion-forward choice she paired with no cami, staying true to her personal style. Her ceremony gown by KATHERINE TASH and a sparkling CLIO PEPPIATT mini dress for the reception continued the effortlessly chic theme.

The rooftop ceremony was officiated by a close friend who masterfully blended Jewish and Greek traditions, bringing laughter and tears. Diana walked down the aisle to a string quartet version of “Landslide,” a song that brought out the emotions of the moment as she walked with her father.

The couple made the most of the HOTEL CALIFORNIAN’S layout, hosting cocktail hour in a charming courtyard with a circular bar adorned with lemons and florals. Signature drinks included Aperol Spritzes and Greyhounds, nodding once again to the Mediterranean-inspired setting.

One of the most memorable moments of the evening came during the reception, when country singer Gary Allan — a friend of Diana’s father — surprised the couple by performing their first dance song live. A band and DJ kept the dance floor full, with a final burst of energy provided by disco balls and a limoncello toast to kick off the party.

Diana and Leland ended the night knowing they’d created a wedding that felt like them — stylish, intentional, and full of heart. Afterward, the couple jetted off to Japan for a 14-day honeymoon that included glamping adventures and a traditional onsen stay — the perfect beginning to their next chapter.