A Wedding Planner's Destination Weekend in Big Sur


Callista Sessler and Jonathan Osborn are adventure-seekers. The couple first met in a finance class senior year at Syracuse University, and just nine months later, they hopped in a car, drove 3,000 miles, and made the West Coast their home. From their new base in Santa Monica, California, Callista says they continued on new adventures, driving up the coast whenever they could escape work for a long weekend. But perhaps their greatest adventure took place in September 2014, when they spent seven days camping and hiking up to an elevation of 19,341 feet atop Mount Kilimanjaro. Once at the top, Jonathan got down on one knee. "With six layers of clothing giving me the lovely profile of the Michelin man, hair frozen to my face, and fingers so swollen I couldn’t quite get on the ring, I said a shivering but ecstatic yes," Callista recalls. (Her dual engagement ring and wedding band is now engraved with the summit height to "serve as a memory of how far it (and we) traveled for that incredible moment," she says.)

For their wedding, the adventurous couple selected a destination closer to home. "We chose to escape to Big Sur on our eight-year anniversary along with an intimate group of our nearest and dearest to celebrate in a way that most represented us," she explains. "Big Sur holds a special place in our hearts." There, Callista, Jonathan, and their 35 guests enjoyed a long weekend of festivities planned by the bride, who is the wedding planner behind Callista & Company. "I was fortunate to be completely in my element while planning my own wedding," she says. Ever the event pro, she enlisted an all-star team of vendors, including Lacie Hansen who was on hand to capture every special moment and gorgeous detail, so keep reading to see all the creativity come to life. Seriously, get your Pinterest boards ready because Callista and Jonathan's wedding is nearly as epic as their Mount Kilimanjaro proposal!

"With our 35 guests traveling in from 12 different states, we wanted everyone to have a memorable and cozy extended getaway," explains the bride. "Our eight-year anniversary fell on a Monday, and we chose to hold the wedding on that date so all the attendees could enjoy a full weekend in the area before our big day." When guests checked in on Friday, they found curated welcome boxes filled of local goodies, like Carmel Valley honey, Anchor Brewing beer, and wine from nearby vineyards.

The couple's invitation suite was just as thoughtfully designed as the welcome gifts. Invites were printed on 100 percent recycled paper from Silk & Willow and adorned with a redwood tree logo. "The longevity of the redwood tree is a symbol for our marriage standing the test of time," Callista says. The logo was woven throughout the wedding's details from the leather coasters in the welcome boxes to the custom tasting boards (for beer) at the welcome reception the night before the wedding.

The couple welcomed guests with a reception on an stunning outdoor pavilion at Ventana Inn. They selected different venues for the welcome party and wedding in an effort to show their guests more of what Big Sur has to offer.

During the welcome, they surprised guests with mini (personalized!) beer flights for tasting, as well as almond cakes, which were hand painted with each guest's name.

The bride shopped at the Monique Lhuillier flagship in Los Angeles, ultimately selecting an ivory lace cap-sleeve sheath as her wedding dress. She paired the gown with Tiffany & Co. tanzanite earrings, a gift from Jonathan that doubled as her "something blue." "The stone was first discovered in 1967 by Tiffany & Co. and is only found in Tanzania, near the base of Mount Kilimanjaro where we were engaged," she says.

The bride carried a unstructured bouquet of white blooms, while her 'maids carried smaller versions that coordinated with the same organic look. The guys' boutonnieres featured sprigs of greenery tied together with ivory ribbon.

The couple personalized the ceremony with music by Elan Artists. A string trio played as the bride walked down the aisle to Johann Pachelbel's "Canon in D" and as the newlyweds exited to "All You Need is Love" by the Beatles.

"The incredible ceremony arch by Studio Mondine felt plucked from the surrounding landscape," says the bride. They exchanged vows beneath that altar in a ceremony they worked with their officiant to design. One of their favorite elements was the reading of an Irish wedding blessing.

At the end of the ceremony, guests showered the newlyweds with a hand-picked selection of dried flowers.

When designing the reception space, Callista used unique textures (wood, leather, and brass) that complemented touches of orange, a nod to the couple's alma mater, Syracuse. Each table was topped with arrangements of golden mustard roses, along with ceramic plates, wooden chargers, and brushed gold and wood flatware.

During dinner, the bride's parents popped open a bottle of vintage champagne (from the year they were married) that was given to them on their 30th anniversary. "It was such a special moment," Callista says.

After dinner, guests moved over to a fireside lounge area, where they relaxed, enjoyed one another's company, and took in the beautiful Big Sur views.

Callista and Jonathan cut into yet another almond cake before hitting the dance floor with their 35 guests. "Having an intimate wedding allowed us to spend quality time with our closest friends and family," she says. "I so dearly cherish each of our guests who made the trip out for our wedding."

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