A Movie-like Capri Elopement (& Proposal Story!)

The Ultimate Mediterranean Capri Elopement – Rochelle Cheever 40

Okay, get your hankies out, we have another candidate for best Bridal Musings proposal story ever!

It’s hard to not gush about how cute Jennifer & Jack’s engagement story is without totally giving it away, but we’ll set you up for with a little movie-like lead-in. Visiting family in South Carolina, Jack was ready to propose to Jennifer with the plan ready for action. But of course, as they do, other family surprises kept getting in the way. With failed attempt following failed attempt, the groom-to-be was forced to table his proposal for another trip as the bicoastal couple flew their separate ways…

We’ll leave the rest of the proposal story in the hands of our lovely couple, but it’s not just their engagement that was cinema gold! In true dramatic form, Jack and Jennifer jetted off to the cliffs of Capri for their stunning elopement. With cinematic views of the Mediterranean and an obligatory boat ride along the Amalfi Coast, we are giving this wedding a full 100% on Rotton Tomatoes.

The Proposal

After five years of dating, Jack had planned on proposing over Thanksgiving weekend, but with his youngest brother’s own engagement party that weekend and other festivities planned, he never found a good time to do it. After all else failed, he was going to propose the Sunday morning before we were to head to the airport, but unbeknownst to him, his middle brother and sister-in-law were heading off especially early that morning to celebrate their wedding anniversary. This would all set the stage for an amazing proposal.

On our plane ride from Columbia, SC to Charlotte, NC, he was planning the next best time he could see me and how he would do it. At the time, he was living in New York and I was living in California. His plane was leaving shortly after we landed in Charlotte, but I had quite the layover. On the way to his gate, I mentioned that a seafood place looked nice and I’d probably stop there and waste some time during my layover. I kissed him goodbye, watched him board his plane, and then headed to the restaurant.

About an hour later, I felt a tap on my shoulder and it was him! I had no idea what to expect. He told me how he had planned to propose over Thanksgiving, how things just didn’t work out, and how he realized while sitting on his plane that he just couldn’t wait any longer. The jetway had already been taken away before he grabbed his bag and rushed up to the front and asked to get off. It was like a movie scene! It’s hard to surprise your girlfriend of five years with a proposal, but I literally didn’t see that one coming.

After he proposed, we both changed our flights to around the same time that night and spent the next few hours drinking champagne, hanging out, and I bought some new heavy coats in preparation for New York!

The Dress & Attire

They say a bride should list her top three priorities when it comes to planning a wedding, and one of those was definitely the dress for me. I wanted something timeless, classic, elegant, and surprisingly, I found it rather quickly. My third stop for dress shopping was Hayden Olivia Bridal in Charlotte, NC, and the dress was I chose was one of the first ones I tried on there. It was part of a trunk show that was leaving within 24 hours, so I didn’t have long to make up my mind. It was a pretty easy decision as I couldn’t stop thinking about it after I left the store. Now that it’s all said and done, I’m 100,000% sure I picked the right one. My dress was the “Candice” design by Anne Barge. My husband also kept it classic and wore a black tuxedo from Brooks Brothers.

Favorite Moments

Our vows were exchanged on a cliff overlooking the Mediterranean Sea at the Hotel Caesar Augustus. We had a string quartet, and the hotel provided an arrangement of fresh seafood, delicious appetizers, and celebratory champagne to enjoy as soon as we walked down the aisle as husband and wife. The whole thing was amazing.

We will never forget walking around Capri, Italy and feeling like movie stars for the day. Everywhere we went, we were stopped by locals and congratulated. Next on our list was a boat ride around the island. That was probably my favorite part of the day. By this time, we had taken all of the most important pictures and could simply relax and enjoy seeing the island via boat. Once back at the hotel, we enjoyed an intimate dinner in a private, cave-like setting at the hotel overlooking the ocean. It was a day we will never forget.

The Honeymoon

After our wedding, we spent an additional two days at the Hotel Caesar Augustus (where we were married) before taking off for six days in Florence. We stayed at NH Collection Firenze Porta Rossa and enjoyed tours around the city as well as wine tasting in Tuscany. Known as one of the most romantic cities in the world, I highly recommend it for your honeymoon.

The Ultimate Mediterranean Capri Elopement – Rochelle Cheever 35

Advice to Other Couples

When I planned my wedding, I first picked the top three things that were most important to me and took care of those first. For me, that was venue, dress, and pictures. Even if those aren’t in your top three, you definitely want to start booking those early. Probably not a bad idea to book your hair & make-up stylists early as well. I didn’t order my bouquet until the last minute, and as important as it was to me, I sent about 4-5 different styles and colors I liked to the florist and left it up to them to surprise me. It was gorgeous! If you trust your florist, I’d highly recommend that.

If you’re considering eloping, you should stop everything right now and contact our photographer, Rochelle Cheever. She specializes in elopements and small weddings. She not only took the most breathtaking photos of our day, but she also helped me plan the timeline of the day out that would allow for the best pictures. She knew Capri, Italy like the back of her hand and was able to guide us on where to go after the ceremony. She is amazing!

Also, if you’re considering getting married in Capri, Italy stop right now and contact Hotel Caesar Augustus. They were beyond helpful. They take care of everything from an English speaking officiant, to flowers for the ceremony and dinner, to appetizers and drinks, to the cake, to pressing your gown and having it ready for the day, and literally anything you need. The hotel is also on top of a cliff overlooking the Mediterranean Sea. There are several great spots they offer for ceremonies.