A Gentleman’s Guide to Planning a Fairytale Wedding

Don’t worry, pictures and video are below…

This post may be a little different than the usual educational style you’re used to. This post is simply me sharing more of my personal adventures with you. I’ve already shared my wedding proposal with you in a previous post, and this is the follow up. While it’s personal, please consider this a Gentleman’s guide to planning a fairytale wedding in Italy.

Back in May of this year (2016), Jami and I headed off to Italy to tie the knot in a fairytale wedding on the Amalfi Coast. Each of us has always believed there was more to life than the status quo and routine. We’ve moved across the country without a plan, thrown caution to the wind and started new business ventures, and decided that life was more than the mundane. So you can imagine how magical it was when we decided to get married non-traditionally.

We chose the Amalfi Coast in Italy as our destination, and I got to work planning all the details. It was incredible, but it was also a lot of work to make happen. Because we weren’t having any guests, family, or friends, we didn’t need to plan for that… but we needed everything else. If you’re planning to run off to Italy to get married, here are the steps I took to make sure our fairytale came together like, well, a fairytale…

Research Everything

I mean everything. Research the culture of where you want to go. Look into how touristy it is. Explore how foreign-friendly it is. Is the language difficult to speak or understand? How accommodating are they to english-speakers? Get on TripAdvisor and read everything about your potential destination so you are keenly aware of the pros and cons you may encounter. You’ll learn which hotels are worth it, and which are not. You’ll also learn tips and tricks to making the most of your experience.

I started reading reviews, comments, opinions, and articles on some of the places on the coast weeks before we booked the flights. Once I knew where exactly we were going, I began learning the language and the cultural idiosyncrasies so we wouldn’t stick out like sore thumbs. The point to remember is to not appear to be an ignorant American tourist. Look, I love America as much as the next guy, but we often make terrible impressions when we visit other countries. Don’t be that guy.

Book Your Hotel + Venue + Flights

You can skip this step if you’re using a travel agent. Just make sure where you’re planning to have your ceremony, reception, dinner, or any other event is available, along with your hotel (if they’re different) on the days and time you would like. Once that’s done, book them all at the same time.

We stayed in the stunningly beautiful Hotel Onda Verde in Praiano for a couple of reasons. The first is, they offered an inclusive package that allowed us to book our stay with half-board included. This means we could eat at the hotel restaurant (either lunch or dinner), and it would be included in the price of the stay. Breakfast is always included, and absolutely the best breakfast you’ll find anywhere. I still dream about the fresh fruit, cappuccinos, and the view on the terrace.

The second reason we chose Praiano is it’s location. Located between Amalfi and Positano, it offers easy boat access to either city (also by road, but traffic gets very congested so boat is always better), but is quieter. Praiano doesn’t offer any real shops or tourist destinations. Yes, there are restaurants serving unbelievably good food, and local markets to get fresh produce, but the t-shirt shops and tourist traps are nowhere to be seen. This keeps traffic and noise very light. Praiano –and Hotel Onda Verde– proved to be one of the best decisions we ever made.

Find Your Photographer

Because we were traveling without friends or family, we knew we had to make sure all our moments were captured for everyone back home. I spent two weeks reviewing local photographers in the area before choosing ours. We were looking for just the right mix of creativity and natural (unprocessed) imagery. We found the incredible Frances Heath. She was more than we ever imagined in a photographer, and we quickly became friends with her and her husband Bruno (who also took care of our live music).

The pictures speak for themselves, right? Frances beautifully freezes on film the natural beauty of the moment, the scenery, and the emotions that bring it all to life. She truthfully manages to capture more than what you may remember. Sure, you remember how gorgeous that moment was with the perfectly blue water and white clouds, but you’ll see the finished picture and its magnificence is staggering. Frances is gifted and we were incredibly lucky to have her on our team.

Find Your Filmmaker

Yes, I said filmmaker instead of videographer. There’s a big difference between them. After speaking with our photographer, she suggested Luigi de Gregorio for our wedding video. These two are truly a life-changing pair of artists. Luigi is a filmmaker. Why is this designation important? Because you are capturing the greatest moments on the greatest day of your relationship, and you have to ask yourself…

“Do I want my wedding video to be an hour long and look like it was recorded by Uncle Randy on a Handycam, or do I want it to look like an epic highlight reel out of a Hollywood love story?”

I’ll let the film below answer that question for me.

Blake + Jami Wedding on Vimeo.

Coordinate & Delegate

Once I had the hotel, flights, photo, and video squared away, it was time to move onto the other details. Because this was a symbolic ceremony (outside of a church), we could do it anywhere. We planned to go over to Italy, get married with all the bells and whistles of love, and then return to the States to legally get the deed done. Using this plan, we weren’t tethered to any laws or waiting periods overseas.

At the suggestion of both Frances and Luigi, we connected with Catherine Bradfield for our planning and officiating. Kate is amazing. She knew we needed to get everyone on the same page, while Jami and I are still living 7 hours behind schedule. Knowing I wanted a sunset wedding and our hotel was east-facing, Kate helped secure the truly breathtaking Casa Angelina Boutique Luxury Hotel on Praiano’s west-facing cliff for the wedding day. She also made sure our cars and boats were arranged on time, and then brought it all together by officiating our ceremony.

If you’re on or near the Amalfi coast and need someone to put your itinerary together for your big day, I can’t say enough wonderful things about Kate. She’s played a huge role in planning a fairytale wedding for us.

We had live music, a gorgeous view, an incredible dinner, and a lifetime of memories all captured on camera. None of this was possible without us first deciding that we wanted to think outside the box and escape the ordinary. If your definition of a fairytale wedding involves the most beautiful place on Earth, I highly recommend you make the Amalfi Coast your destination… with or without your family.


If you have any questions or comments about how we put this trip-of-a-lifetime together, please reach out.
If there’s anything I can do to help make your big day even better, don’t hesitate to ask.
As always, please share your thoughts and comments below so we can connect!

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The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.