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Home > Italy wedding

A Romantic Destination Jewish Wedding at Villa Medicea di Lilliano, Tuscany, Italy

06/11/2025 by Karen Cinnamon

Naomi and Nathan, Villa Medicea di Lilliano, Tuscany, Italy

We love a Jewish wedding in Tuscany! And Montreal couple Naomi, a luxury travel concierge and planner, and Nathan, an accountant, had one of the best.

Their big day at Villa Medicea di Lilliano featured the chicest mismatched bridesmaids, a Mamma Mia-inspired flash mob, the most incredible kosher catering by Cantina Giuliano, and so much more.

To make the celebration of their dreams a reality, the couple opted to work with Smashing The Glass Recommended Vendor Sandro Poli of The Couplers. In Naomi’s words,

If you’re Jewish and getting married in Italy he’s the guy for you!! He’s so amazing and super helpful. He really helped us with everything from A-Z. It was truly amazing working with him especially since he spoke Italian and is also Jewish so he really knew the ins and outs of everything. I couldn’t recommend him enough. He truly became family.

Sandro, who worked in fashion before becoming a wedding planner, even sewed sleeves onto Naomi’s dress 20 minutes before the chuppah!

Don’t miss the wonderfully stylish photos by Isabella Pratesi – they’re truly something special.

Read on for all the details in Naomi’s own words…

Naomi and Nathan, Villa Medicea di Lilliano, Tuscany, Italy Naomi and Nathan, Villa Medicea di Lilliano, Tuscany, Italy Naomi and Nathan, Villa Medicea di Lilliano, Tuscany, Italy Naomi and Nathan, Villa Medicea di Lilliano, Tuscany, Italy

How We Met

Naomi, the bride: Nathan and I grew up in Montreal and are the same age. The Jewish community of Montreal is incredibly special and everyone kind of knows each other. Growing up we always kind of knew of each other (we went to different Jewish schools though). The summer of 2021 my best friend suggested going on a trip to Greece with a couple of her friends. At the time she was seeing Nathan’s cousin so she invited him and he invited his friends. We ended up doing a big trip to Greece! There is where Nathan and I’s friendship started. And then once we got back we pretty much fell in love right away. We started dating two weeks later.

Funnily enough earlier that summer Nathan worked for my dad (my dad owns a kosher pizza restaurant) and Nathan was doing deliveries as a summer job! So my dad already loved him and he was accepted into the family pretty quickly. On our way back from Greece we were all supposed to go to Israel but due to Covid our flights got cancelled. Him and his friends ended up going to Paris (they are all from there) and by fluke I ended up stuck in Paris for 3 days. We hung out every day. Honestly we’ve been inseparable since.

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Eternal City Jewish Wedding Inspo at the Rome Cavalieri, Rome, Italy

04/08/2022 by Karen Cinnamon

Rome Cavalieri Jewish Wedding Styled Shoot

There’s no place like Rome for a Jewish destination wedding. The history, the romance, the food… so many STG brides opt for gorgeous celebrations in the Eternal City, and it’s easy to see why. That’s why we’re so thrilled to be featuring this stunning Jewish wedding-themed styled shoot at Smashing The Glass Recommended Vendor The Rome Cavalieri, a Waldorf Astoria Hotel and one of Rome’s premier Jewish wedding venues. Planned by another beloved Smashing The Glass Recommended Vendor, Deborah di Castro, and photographed by Alessia Angelotti, it’s truly a feast for the eyes.

Rome Cavalieri Jewish Wedding Styled Shoot

Rome Cavalieri Jewish Wedding Styled Shoot

FOREVER AFTER IN THE ETERNAL CITY

The Rome Cavalieri is a peaceful oasis immersed in a private 15-acre Mediterranean park located at the top of Monte Mario hill. From the hilltop, you and your guests can enjoy unique and enchanting views of the Eternal City. And if you’re looking to have your chuppah in the majestic Great Synagogue of Rome, it’s just 6 km from the property.

Rome Cavalieri Jewish Wedding Styled Shoot

Rome Cavalieri Jewish Wedding Styled Shoot

The Rome Cavalieri’s outdoor event space, Terrazza degli Aranci, is Rome’s highest panoramic private terrace offering a spectacular backdrop of the Roman atmosphere for your big day.

Rome Cavalieri Jewish Wedding Styled Shoot

Rome Cavalieri Jewish Wedding Styled Shoot

Jewish Wedding Experts

The Events Planning team at the Rome Cavalieri are pros when it comes to Jewish weddings. In fact, one in ever four weddings held at the hotel is kosher!

The team has the knowledge and expertise to tailor your event to your unique needs, with many special options to make your day truly one-of-a-kind including signature cocktails, custom wedding cakes by Executive Pastry Chef Nuti, authentic Shabbat dinners, and lunches.

The Rome Cavalieri’s kitchen can prepare fully kosher meals as well as kosher-style options, thanks to their longstanding relationships with trusted kosher suppliers, all supervised by a rabbi provided by the Roman Jewish community.

Rome Cavalieri Jewish Wedding Styled Shoot

Rome Cavalieri Jewish Wedding Styled Shoot

The Rome Cavalieri can host weddings of all sizes, from 20 up to 500 guests. With over 29 event spaces to choose from, you will be sure to find the perfect spot for every element of your destination wedding in Rome. 

Rome Cavalieri Jewish Wedding Styled Shoot

Rome Cavalieri Jewish Wedding Styled Shoot

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