How to plan the ultimate destination wedding (in Tuscany)

International award winning wedding photo

Why a Destination Wedding?

Over time—and as we attended the weddings of friends—Guillermo and I developed a deep appreciation for those wedding-related elements that would one day shape our own celebration … and collectively embody the special relationship we share.

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One wedding on Lanai, Hawaii, immediately comes to mind, since it had a pronounced influence over our decision to have a destination wedding. Let me explain:

As a remote place, Hawaii represented a true mini-vacation for most guests. The couple had lovingly planned three fun-filled days of activities surrounding the actual wedding day.

And when people are on vacation, they have a chance to unwind and become more present without the distractions of everyday life.

Specifically, we loved that our friends hosted a BBQ on the beach a few days before their wedding, giving everyone a brilliant opportunity to connect. As a result, on the wedding day, we witnessed remarkable group cohesiveness that you simply don’t see at most weddings.

And voila … the seed was planted for a destination wedding that would make our hearts sing.

Why Tuscany, Italy?

Guillermo and I wanted our wedding destination to be rich in tasty food and wine, while offering family and friends abundant entertainment options (e.g., biking, wine tasting, pool lounging, and sight-seeing).

We also wanted our destination location to represent a similar travel commitment for both of our families—Guillermo’s contingent would largely come from Chile and mine from the West Coast.

A rustic Tuscan vineyard seemed to check all boxes just fine.

I visited Italy before on a spontaneous escape to Rome, but Guillermo had actually never been to Italy. So I was even more excited to experience the delicious Tuscan treasures with my love.

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Why Villa la Selva?

Out of budgetary considerations—and me being a bit of a control freak—we initially opted to plan the destination wedding on our own.

The right location was a top priority for us, and we knew its search would demand time and resources.

And so we scoured countless wedding blogs, bridal magazines, and travel sites for the perfect Tuscan venue.

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It took us about two months to identify and book the Villa la Selva, which at once met our budget and held the promise of a spectacular destination adventure.

Interestingly, the Villa had only started operating as a wedding venue a few years ago. As a result, substantive reviews were hard to come by.

So we really kind of signed up on gut feeling, didn’t have a Plan B, and just knew we had to make it work.

Our friends were thrilled about the idea of a destination wedding in Italy from day one, but we did get a little grumbling from our families … because the requisite travel would prevent some family members from attending.

How did you go about booking your destination wedding venue from a faraway?

We essentially booked the Villa la Selva entirely via email correspondence … and honestly, looking back, I just feel blessed that it all worked out as well as it did.

First dance at a wedding

Our first step—approximately 16 months prior to our wedding—was to decide on a wedding date (and a back-up date) before kicking-off negotiations with potential venues.

Great wedding locations book far in advance … and so we gave ourselves a generous time cushion.

Or so we thought, because several of the venues we reached out to were already booked.

So, our number one tip when planning a destination wedding is to kick-off the planning process as early as possible. If a venue is good enough for your Big Day, chances are high that it’s also good enough for other couples.

The actual administrative process of booking the Villa La Selva was unusual to say the least, and unlike anything you’d probably encounter in the United States: all communication was strictly limited to email, and our deposit (via wire transfer) was requested even before an official invoice was issued or a contract signed.

Hey, different cultures, different ways of doing things, right?

And I guess it didn’t help that neither of us is fluent in Italian (although Guillermo insists he’s perfectly conversant in Italiano :-).

That said, I would encourage brides to not accept such informality—especially for an occasion as precious as a wedding!

Any learning lessons from working with a local (Italian) wedding planner?

Once we realized how challenging it was to book a venue in Italy, we dropped the idea of a DIY approach to wedding planning, and instead hired a local event planner.

The idea was that she’d help us identify, communicate, and hire the remaining Italian vendors, while saving us time and costly mistakes.

In hindsight, working with an Italian wedding planner was one of the most challenging aspects of the entire planning process since we are so accustomed to the responsiveness and attention to detail that American wedding professionals provide.

So our next tip then for brides, planning a destination wedding in a foreign country, is to hire an experienced international event planner. Your time is worth money and the last thing you need leading up to your Big Day is stress.

If you think it’s expensive to hire a professional … just wait until you hire an amateur.

Tell us about the housing options you organized for your guests.

The Villa la Selva was at once our wedding venue, ceremony location, and the primary housing option for our guests.

Unlike a traditional hotel, the exclusive estate Villa allowed us to entertain everyone for the duration of the wedding week in a relaxed, homely environment.

We wanted to create an atmosphere that fostered cohesiveness and enhanced the fun-factor … which routinely entailed group meals, massive bowls of artisan pasta, and endless supplies of Tuscan wine.

The main villa of our venue accommodated 14 rooms. The remaining guests stayed at five farmhouses conveniently located on property.

Our guests were particularly excited that our villa allowed them to bring in food, cook their own meals, and wake up to a lively community breakfast … and, of course, celebrate epic after-parties …

As mentioned, our guests traveled far to celebrate with us. So it was important to Guillermo and me to organize and make available brilliant entertainment options.

Super-yummy welcome dinner? Check.

What about a stunning chateau setting for a wine tour that would educate some … and intoxicate others :-)? Double-check.

Hey, Guillermo and I even got to practice our first kiss in a fun theater setting.

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How did doing an NYC engagement session with Cengiz affect 1) your comfort in front of his lens on your wedding day; 2) your post-wedding shoot?

Doing our engagement session with Cengiz gave us intimate insight into the way he works as an artist, and how his directions to us during the shoot translate into his final photos.

For the sake of imagery—Cengiz’s (in)famous words of wisdom—held a lot more relevance for us after our NYC engagement photo shoot.

For those of you who may not yet be familiar with the concept of For the Sake of Imagery, it touches on the idea that both you the couple and your photographer must get intentional about your photography experience and be prepared do things that most people wouldn’t attempt … if you want photos that nobody else has.

Times Square NYC engagement photos

As a result of having already photographed with Cengiz, we trusted him blindly and passionately embraced his artistic process during the wedding itself … and over the course of our next-day wedding photo shoot.

Our trust in Cengiz’s experience, creativity, and artistic eye was so great that we actually gave him a mandate to review our ceremony setting and communicate to the wedding planner any changes he saw fit.

We were SO happy about our decision, because his subtle adjustments made a real difference in our pictures!

Here’s another Pro Tip: your photographer will spend a significant amount of time with you on your Big Day—even while you’re getting ready—so comfort with and trust in your artist are essential.

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It rained like crazy on the morning of your wedding. There was even talk of moving the ceremony and all festivities indoors. You decided to proceed with an outdoor ceremony. Explain.

Torrential rain threatened to throw a monkey wrench on our ceremony, which was envisioned as an outdoor event from the outset.

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We first reviewed with our wedding planner the indoor alternatives as mid-day the rain still showed no signs of abating.

Then we presented to Cengiz our planner’s indoor recommendations for the ceremony; we briefly went over the pros and cons of the available options, and decided that the garden setting was one of the primary reasons we selected the Villa la Selva in the first place.

So rain or not, we were determined to have an outdoor ceremony.

Cengiz (and his beautifully artistic mind) envisioned a rain-contingency ceremony held under umbrellas, so we coordinated with the planner to procure as many colorful umbrellas as she could get her hands on.

Honestly, we were completely at peace with our decision and would have been thrilled to tie the knot under pouring rain.

The best thing one can do when it’s raining is to let it rain. ~ Henry Wadsworth Longfellow

With two hours to spare, the skies almost miraculously started clearing, and suddenly we were blessed with perfect conditions for our garden wedding ceremony!

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Luckily, Cengiz was still able to make the most out of our umbrellas. See for yourself :-).

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Your wedding reveal, or so-called first-look between the bride and the groom on the wedding day, was nothing short of a fairytale. How did it feel when he first laid eyes upon you?

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Our decision to do a wedding reveal, or first look, was one of the best decisions we made.

The hours leading up to the ceremony were at once exciting, scary, and brimful of emotion—I wanted to share those emotions with Guillermo.

Guillermo is my best friend, and I’m accustomed to sharing my rawest feelings with him … and the reveal was undoubtedly the time when my emotions were at their craziest!

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Right before I started walking towards Guillermo, I remember telling Cengiz how nervous I was … and then as I approached Guillermo, everything around us kind of melted away.

When Guillermo reached behind to embrace my hand before turning to face me, I felt completely at peace. I knew that everything we had poured into the wedding—time, energy, and finances—was completely justified just with that one moment.

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That intimate moment of privacy powerfully set the tone for the remainder of the day. I was no longer nervous, and simply overjoyed to enter into a lifetime commitment with my incredible man … all before they eyes of my dear friends and family.

Importantly, the reveal did not one bit diminish my emotions come ceremony—I still felt raw, unconstrained, blissful joy equivalent to what I experienced during the reveal … as evidenced by my abundant tears for most of the ceremony.

wedding ceremony tears

The Groom’s Perspective of the Reveal:
The first look is something very special. It’s the only moment you two will share alone.

We opted for a reveal, because we wanted to talk to each other and see each other before anyone else did … and it was magical.

Amidst all the craziness of the wedding, remember that the first look is you two … and ONLY you two.

Embrace each other, hug each other, smile with each other.

Reveal during a wedding

If you’d like exchange some words in privacy, use this moment to do just that.

The First Kiss, ring exchange, and recessional often make for splendid photo opportunities. Any tips and tricks?

Practice, practice, practice your First Kiss so it truly takes people’s breath away.

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It’s really quite simple: the moment before the kiss is where the magic happens. Don’t settle for a cavalier kiss, because the lead-up to when your lips first connect can be a hundred times more delicious … and then, when your lips actually touch, the anticipation itself made your kiss even more enjoyable and, incidentally, camera-worthy.

We learned to perfect our kiss during our engagement shoot. It will be the most photographed kiss of your life. So you might as well bring it!

NYC engagement photos

One thing you cannot practice is emotions. And that’s probably a good thing.

It’s important to let yourself fully experience your emotions, even if you’re scared of how it might affect the pictures. I was terrified of crying in front of the camera, but raw emotions are beautiful and priceless, and something you’ll definitely want captured on film.

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The ceremony recessional—the first walk you take together as husband and wife—makes for one of the most awesome, feature-able, and emotionally charged photo opportunities imaginable.

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Best of all, it can and should be planned. So I recommend doing a little research [and communicating your ideas and inspiration to your photographer, planner, pastor, and guests ahead of time].

It makes a difference when your guests join in on the fun, and shower you with something (e.g. flower petals, bubbles, rice, confetti, butterflies, or anything else that has the potential to induce a sense of motion into your pictures). We went for a combination of rice and confetti.

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As you might imagine, the imagery from our recessional stood out among our favs; and we couldn’t be happier.

Here are a few tips to help you spice things up:

  • More is more—it’s all about impact and fun
  • Ask those people who may have joined you at the altar to kindly wait [with their own recessional] until you’ve walked the entire aisle; that’s the only way to ensure the absence of distractions in your photos
  • Consider asking your pastor to gently alert the guests to prepare for throwing action before you start your recessional
  • It matters little whether you do high-fives, look at each other, or look ahead as you make your way down the aisle; however, what is important is that you be intentional, happy, and move in concert energetically
  • For extra credit, consider a second First Kiss in the middle of the aisle; it’s fun and your photographer will thank you

Your dance party was literally off the charts. Who was your D.J.? Did you give him a song list or was it his doing? How did you manage the music selection from NYC?

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Our DJ was incredible! His name is Francis Jay (danceparty.it).

We sent him a selection of songs ahead of the wedding but we did not curate them all … some of our requests to him were “play some songs like this one” or “play songs that mix old and new rhythms and songs.”

He was super-receptive and had the full list that we wanted him to play with him, so it was easy to search for a specific song that we wanted that he hadn’t yet played.

The music selection part was a long one … basically we started the list some three months before the wedding.

While going out, or being in the car, or at any point where we heard a song we liked we listed it. Besides that, it was listening to our iTunes library, Spotify, YouTube, iTunes Radio, Soundcloud, etc for about four nights straight and then collating it, talking about the songs (some songs are awesome … but you can’t dance to them) and finally sending them to our DJ.

Make sure you specify with the DJ ahead of time if you’d prefer to stick to your provided list, or if you are OK with him taking requests from guests or adding in his own mixes. Our guests were not shy and made quite a few requests.

P.S. So, Now What?

We’d love to hear from you—which of Danielle’s destination wedding tips did you find most helpful?

And then we’d like you to share a personal experience from your own destination wedding or one you attended where you felt like something worked really well … or had a positive impact on the overall festivities.

Share your thoughts generously in the comments section below.

As always, thank you for your tremendous support.

XO,

Adagion Studio Principal Photographer

P.P.S.

Btw, do you know of anyone who will enjoy learning about this destination wedding?

Danielle and Guillermo told us how they did it. So now you can help your friends by sharing this post.

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Event Vendors

Photography: Adagion Studio
Ceremony Venue: Villa la Selva
Reception Venue: Villa la Selva
Wedding Planner: Tuscan Dream
Floral Design: Elena Bindi
Wedding Dress: Carol Hannah
Brides Shoes: Oscar de la Renta
Grooms Attire: Ralph Lauren Black Label
Catering: Galateo
Cake: Galateo
Ceremony Music: Chiara Trallori
Invitations: Together & Company

About the Author

Cengiz

Cengiz is the founder of Adagion Studio and Zero Gravity Learning. His unique creative vision combined with a rare ability to bestow surreal rock star auras on real-life people have led to his recognition as one of the most internationally respected elite wedding photographers working today.

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