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A Beautiful Positano Wedding


December 29, 2021
Words by Kristi Blane
Photos courtesy of Maison Pestea

If you are familiar with DID and our real wedding stories, then you know we don’t typically present them in a Q&A format. However, on occasion, we will have a wonderful chat with a couple who tells their story better than we ever could. When we interviewed Jae and Cassidy about their breathtakingly gorgeous wedding in Positano, Italy, their insight into planning an overseas wedding during the pandemic was invaluable.

We invite you to sit back, relax and take a journey through Jae and Cassidy’s wedding story!

 How did you meet?
A: We met and started dating in July 2018 in Chicago. We “matched” on a dating app and decided to get a few drinks at a restaurant with a picturesque rooftop. Chicago in the summertime is gorgeous, and that day was no different. The weather was perfect; not too hot, not too cold. We ended up talking for hours and Cassidy broke conventional dating rules and decided to ask Jae on a second date before the night was over. A year later, we ended up moving into our first apartment together just a few blocks from where we had our first date!

Q: Why did you choose to do a destination wedding?
A: We always wanted a more intimate wedding and to get married somewhere memorable. However, we also got engaged in February 2020 right before the Covid-19 pandemic hit, so a smaller, more intimate wedding made sense. Our families also live in different parts of the country, so we knew that people would be traveling to our wedding anyways, no matter where we held it.

Q: How/why did you choose the location/destination? Did you run into any issues specific to this destination and how did you resolve them?
A: We both love to travel, and while dating we made a list of places we’d like to travel together someday. Italy was on that list and we hadn’t crossed it off on previous trips together, so when we got engaged and started thinking about where we wanted to get married it quickly came to mind. We spent a few weeks researching locations and potential venues in a few different options, like Tuscany, Lake Como, and Ravello, before deciding that Positano was the perfect fit for us. Positano is a small cliffside town on the Amalfi Coast with gorgeous views of the Mediterranean and Villa Magia was the perfect venue where we could rent a private villa for our guests and hold our ceremony.

Q: What helped you the most in the planning process?
A: Having a wedding planner! We initially tried to plan our wedding in Italy by ourselves, but it was a challenge, especially with the pandemic. We needed someone with experience to help us plan our wedding and direct us to the right people. We found the perfect wedding planner at an affordable price that made the process much easier.

Q: What were the travel logistics like for your guests? Did you run into any issues and how did you resolve them?
A: Our guest list was small by design as we knew that Covid would make traveling internationally more of a challenge. We also traveled from four different states to reach Italy, so the logistics of people traveling on different airlines through connecting airports and into different parts of the country on different days was a little hectic (not to mention changing Covid protocols and requirements).

Q: Do you feel you spent more or less money by choosing to do a destination wedding?
A: In all, we probably spent less on our wedding abroad than we would have spent on a wedding in Chicago. Our dollar went further in Italy, and we were able to prioritize our spending on creating a memorable experience for everyone with us. If we had held a wedding in Chicago, we would have been able to celebrate with more of our friends and family, but that comes with a bigger price tag!

Q: How do you think your wedding would have been different had you not held it away from home?
A: Going overseas for a wedding was not stress-free. At times, we weren’t sure if the wedding was going to happen because of ever-changing Covid travel restrictions.  But we still think it was less stressful than having a local wedding, as it would’ve been difficult to narrow down our guest list and expect family and friends to travel from different parts of the country during the pandemic.

Q: Overall, do you have any special advice you would like to share with our readers to help prepare them for their day?
A: Get a wedding planner early in the process and prioritize your budget on getting a great photographer. With a destination wedding, we knew that our guest list would be much smaller than it would have been had we married in the US, so it was essential for us to choose a photographer that could capture the day so we could share it with everyone who couldn’t celebrate with us in person. Having a wedding planner made the process so much less stressful, especially given that neither of us speak Italian and had never been to our destination before. Trusting Victoria and feeling confident that she could navigate the intricacies of planning from abroad made the process much more enjoyable.


Vendors: Photographer: Peggy Picot of Maison Pestea; Wedding Planner: Victoria Morris of Sophisticated Weddings Italy; Ceremony/ Reception Site/ Cake: Villa Magia; Florist: Rosalinda Flowers Wedding Lab; Hair & Makeup: Joanna Falanga of Makeup Artists Sorrento; Gown Designer: Jenny Yoo; Groom’s Clothing Designer: Balani; Boat: Positano Boats; Carmela Cesarano of Italy Celebrant

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