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…
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.
A Wedding in Tuscany
We got married in the Tuscan country side about 20 minutes away from Florence at this beauty villa called Villa Medicea di Lilliano. I always wanted to do a destination wedding, as if we had gotten married in Montreal the wedding would’ve been with 500 people and I prefer smaller weddings.
The first time I visited Italy in 2021 and I fell in love with it. The second I landed I looked at my best friend travelling with me and I said “mark my words I’m getting married in this country” and then 2025 came around and I did! My first choice was Israel but due to the war it unfortunately didn’t work out.
The Perfect Planner
My mom really helped everything come together and I truly couldn’t have done it without her. Additionally we had the most amazing wedding planner – Sandro Poli with The Couplers. 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.
About 20 minutes before my chouppah we had agreed that Sandro would sew sleeves onto my dress because he used to work in fashion for years before becoming a wedding planner. So right before my chouppah I’m standing there with my friends and he’s just sewing sleeves onto my wedding dress like it’s normal. It was hilarious. He’s truly a genie and a magician. Love him so much!!!
Hair + Makeup
Hair and makeup was done for me by Baj who is the owner of a salon called Ciro Villa d’elle Terme in Florence. Her and her team are truly AMAZING!! I’ve never felt prettier in my entire life she captured exactly what I wanted which was to still look like myself.
I also forgot to mention the hair and makeup for my bridesmaids – Alessia Corti Wedding, she was so incredible and everyone looked so beautiful!!!
An Atelier Eme Dress
Funny story about my dress. I tried on a couple in Montreal and got an idea of what I liked. The following week I flew to Florence to check out the wedding venue with my mom. On a random Friday we were walking about Florence and saw this wedding dress store – Atelier Eme. My mom was like let’s go inside and check it out and I didn’t want to but she pushed me and said why not you never know.
We walked in and I tried 4 dresses. Out of the 4 I loved 2 but only certain things about each of them and I told my mom I wished we can bring these together. We spoke to the manager who spoke to her seamstress and they ended up saying we can. So without ever trying it on I said let’s do it and bought my dress without knowing what it would look like. This was back in November.
My first try on was in May and during those months the seamstress sent me a drawing of what my dress would look like and I loved it. May came around and I was so nervous to try it on as I really didn’t know what it would look like in person! The second I tried it on I feel in love with it!! It was the perfect dress and fit me perfectly. We had to touch it up slightly and then the next time I tried it on was a week before my wedding (in august). And it fit like a glove!! It was the most beautiful and perfect dress and the ladies at atelier eme Florence were the sweetest and the best!!
Bridesmaids
My bridesmaids were all INCREDIBLY beautiful!! I was super chill with their dresses my only ask was pastel colors! I wanted everyone to wear something they’re comfortable in but also thought pastel dresses would be beautiful in Tuscany. It was truly perfect.
Ceremony & Chuppah
For the chouppah itself I wanted to keep it super simple as I really thought the view was decor enough. However, for the ceremony we knew we wanted to add the shofar as it was Rosh Chodesh Ellul and I felt it added a special touch. We also (obviously) ended the chouppah with a prayer for the hostages and our soldiers.
Ketubah
I let Nathan choose our ketubah and he chose a spectacular one. An artist and rabbi in Montreal designed it for us, Rabbi Chaim Sheriff. He is incredible. All of his work is so amazing and I think I had the most beautiful ketubah ever.
Our music choice
We brought in a DJ from Montreal – Dj Coco. He was truly amazing!!!! We also brought in Tal Vaknin from Israel for our chouppah and our first dance. The second he came out with the song Mon Amour (Hebrew and French version) we knew it was going to be our first dance song.
Nathan is French (born in Paris) so it was important for us to incorporate some French into the wedding. During the chouppah Tal sang boee kallah in the Andrea Bocelli version to really tie in the Italian theme of the wedding. It was truly magical, his voice is just incredible. He also sang our first dance song live which was truly so special.
Flowers
My florist – Jessica with Dreaming Flowers Wedding is INCREDIBLE. She truly captured exactly what my Pinterest board looked like. She is so talented and creative and I can’t recommend her enough.
Our centrepieces were these beautiful flower arrangements flowing around with some Italian seasonal vegetables to add in some slight details. It was incredible. The bridesmaids all had bouquets matching their dress color and my bouquet was just the perfect mix of simple and classy. Exactly what I wanted.
Photographer and videographer
My photographer and videographer were INCREDIBLE!!! My photographer Isabella Pratesi and videographer Francesco Vannetti with Wedding Key Studio and their teams are incredible.
Some of our pictures look like they can be in the cover of vogue. They are so talented and are so fun to work with. Truly artists in their crafts.
Food and cake
My cake was one of the favorite parts of my night! There aren’t many kosher catering options in Florence but Cantina Giuliano are the best!!!! Eli and Stefano are truly INCREDIBLE. The food was insane.
They also own a kosher winery right outside of Florence which is a must visit!! For my wedding cake Stefano and his team constructed a giant millefeuil cake with raspberries in front of our guests. Nathan and I obviously helped! And then we cut in front of everyone. Not only was it beautiful but it was also DELICIOUS!
Extra Details
One of my favorite parts of the night were when my bridesmaids and groomsmen put together a flash mob in the middle of the dance floor. I love Mamma Mia, it’s my favorite movie, my bridal shower was mamma Mia themed (which my aunt put together and it was incredible). I watch the movie probably once a month. My best friends know that and put together a dance to dancing queen. It was INCREDIBLE to stay the least. I also can’t forget to mention the speeches – both of our dads spoke beautifully. However, my younger sister Emma (she is 13) spoke beautifully and made everyone cry.
Advice to couples currently planning their wedding
The best advice I was given was don’t stress the small things. Things will go wrong but who cares, just enjoy the day. I was super relaxed because at the end of the day you’re getting married to your best friend so who cares if some things aren’t perfect. All that matters is that you’re having the best day. The day will fly by so take in every moment.
NAOMI & NATHAN’S LITTLE WHITE BOOK
Photography – Isabella Pratesi
Videography – Wedding Key Studio
Venue – Villa Medicea di Lilliano
Planner – The Couplers {offers 10% discount to all members of Smashing The Glass’s Brides Club}
Bride’s dress – Atelier Eme
Hair + Makeup – Ciro Villa d’elle Terme
Bridesmaids’ hair + makeup – Alessia Corti Wedding
DJ – Dj Coco & Tal Vaknin
Catering – Cantina Giuliano
If you’re a Jewish or Jew-ish bride-to-be, you’ll want to join Smashing The Glass’ Brides Club. Guided by the world’s number 1 Jewish wedding expert, Karen Cinnamon, Brides Club is the private community for Jewish and Jew-ish brides that removes wedstress and indecision and gives you what you need to plan with confidence during these uncertain times. Join our Brides Club here.
