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Home > Tuscany 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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Daphna & Godwin | Tuscan Castle Jewish Wedding, Tuscany,Italy

19/07/2013 by Karen

Tuscan-Castle-Wedding
I have a delicious destination wedding for you today. And they don’t come much more delicious than the beautiful Castello di Modanella in Tuscany – a castle in Italy which is also a vineyard where they make their own wine and olive oil. A stunning venue with gorgeous views and a wonderful ceremony (incorporating the James Bond theme tune) it was the perfect location for Daphna and Godwin to hold their very fun wedding weekend.

Daphna and Godwin (or D&G as they like to brand themselves!) met at work and were immediately attracted to each other. They kept their relationship quiet in the office so none of their colleagues knew that they were actually dating, and when they announced their engagement  15 months later it’s fair to say that all their colleagues were pretty shocked! The wedding itself stretched over a long weekend and took months of meticulous planning. Here’s Daphna with the D&G w-day story:
TUSCANY WEDDING
TUSCAN CASTLE WEDDING ITALY
A WEDDING WEEKEND ABROAD
Daphna, the Bride: I had always liked the idea of getting married abroad, as I had been to lots of weddings in England and wanted something different. As a bride you don’t actually get to spend much time with your guests so I wanted everyone to be relaxed on holiday for the whole weekend. That way at least you get to actually see your guests and for this purpose we organised various nights before the wedding day itself like a BBQ and a pizza night. I thought a destination wedding would be fun because everyone gets into holiday mode and ready to relax and party without having to worry about going to work the next day.

We thought about Spain and Italy as we love both countries, (we have no particular tie to either country, although I did study Spanish and lived in Madrid for a year, so I do love it) but in the end Italy won as it has better food & was a little classier! We looked at the Amalfi Coast too as I really wanted somewhere by the sea, and it is really romantic and gorgeous, but after researching we found that the Amalfi Coast has a lot of strict rules about music, ie lots of places only allow background music, and the party has to stop at 11.30pm etc. As we wanted a big party, this wasn’t really acceptable for us.
TUSCANY CASTLE WEDDING ITALY 1TUSCANY WEDDING_07
Also, it was proving hard to get married outdoors and as far as I was concerned there is no point getting married abroad if it’s not outside in the sun! In the end we decided on a castle in Tuscany, where they make their own wine. It has a big lake, and various swimming pools, so it had the water aspect I wanted. The venue offered wine tasting & trips to their vineyards. There were no restrictions about what time the party had to end (we ended up having a pool party after the wedding till 4am to finish off the alcohol!). Most importantly the food at the castle is absolutely fantastic – I cannot rate them highly enough. They have their own restaurant that is open to the public that is practically Michelin starred – every dish you try is superb.

Additionally there was accommodation for over 200 people, so it meant that everyone from the wedding could stay in one place, which is something else I wanted. I didn’t want everyone dotted around –  it’s so much nicer to have everyone together. The views from the castle are absolutely beautiful, right amongst the rolling Tuscan hills.

The venue is owned by a family friend, so it made the whole affair really personal to us, as it felt like our family was there every step of the way helping us organise the wedding.

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