“From the onset, we were overwhelmed at the thought of a big wedding in Chicago or our hometown of St. Louis. We visited venues in both cities, but nothing clicked. We began to think a destination wedding would be a great option,” Claire and Brad say. Bride, Claire had visited Italy years ago and fallen in love with the idea of an intimate Italian wedding with friends and family. 

Luckily, the couple’s families were extremely supportive once Claire and Brad explained their discomfort with a big wedding, they understood why the couple decided to look abroad. The idea was to take the budget for one day and, instead, create a multi-day experience with friends and family away from home. “We knew we would never get that opportunity again,” the couple says.

Early on, Claire and Brad connected with Lisa Jaroscak at Storybook Weddings & Events. At the start, they met with Lisa, explained their vision for an outdoors Italian countryside wedding in the late fall. Lisa steered the couple to the Puglia region of southern Italy and proposed several venues. “We eventually arrived at Masseria IL Frantoio for its charm, setting, and reputation of exquisite cuisine,” the two explain.

Their planner worked with her Italian counterpart, Lucy Rigby, to make the couple’s dream a reality. In addition to introducing them to a dreamy venue, the planners connected the couple with their florist, Bird and Bumble – who they say were instrumental in establishing the aesthetics of the celebration – and their photographer, Bonphotage – who elevated every precious memory. Additionally, Lisa and Lucy not only kept in close contact with the couple in the year leading up to their wedding, but they were also able to travel to the Masseria to taste the menu, survey the grounds and experience the accommodations.

“This was single-handedly the biggest advantage of having a wedding planner – Lisa and her Italian counterpart, Lucy, handled all the communication between the Masseria and the Italian-speaking vendors,” Claire and Brad say.

As helpful as their planners were, the couple did take a few items into their own hands. Brad is a graphic designer, so he worked long and hard to design everything from the invites and menus to the welcome bags and itinerary cards. “We made a concerted effort to draw a connection to the region and chose a typeface designed by an Italian type foundry,” Brad says.

Thankfully, planning challenges were few and far between for the couple. While the Masseria’s remote location added its own challenges for transportation, it was this remoteness that built the allure. Brad and Claire wanted to make sure their guests would be taken care of after all of their effort to arrive at the remote location. So, they ended up spending more than they’d budgeted in order to subsidize their guests’ rooms and a group excursion to the neighboring towns of Alberobello, Polignano a Mare and Ostuni.

In the end, although not everyone they’d hope for could attend, the two say that is a reality they were willing to face in order to make their destination wedding dreams come true.

Vendors: Photography: BONPHOTAGE; Planner: STORYBOOK WEDDINGS; Venue: MASSERIA IL FRANTOIO; Wedding dress: ALEXANDRA GRECCO; Bride’s shoes: LOEFFLER RANDALL; Floral: BIRD AND BUMBLE; Hair: MIKY BASILE; Makeup: LUCIANA VENDOLA; Music: BLUE MOON JAZZ TRIO