Q and A: planning an Italy destination wedding

10 years ago, we flew from Canada to Italy and got married in what was once a tiny medieval village in the Italian countryside.

At the time (and at the risk of making us sound absolutely prehistoric), destination weddings in general were still a bit of a novelty. We’d heard of couples getting married at Caribbean resorts, but did not know anyone who had gotten married in Europe. Planning for our Italy destination wedding was an entirely new adventure, and we went into it completely blind. None of our friends had any advice for us, attending local wedding conventions were largely unhelpful, and we were left scouring the internet and jumping down forum rabbit holes.

In my humble opinion, I think we cobbled together a fairly decent and unique wedding. 😉

Since then, we’ve have plenty of friends and other couples ask about our wedding in Italy. We were even featured in Canada’s Today’s Bride! As a part of our series on destination weddings, we thought we’d put together our own Q and A, magazine style, with some of the behind-the-scenes and nitty-gritty involved in planning our Italian wedding.

This one is for the planners (and the dreamers ;).

Wondering if a destination wedding is right for you? Be sure to check out our articles: 10 Reasons to Have a Destination Wedding, and Reasons Not to Have a Destination Wedding.

How did you choose Italy for your wedding destination?

To be completely honest, we were inspired by a rom com. 😛 (Guess which? Answer * at the bottom of the post. 😉 They’d spent the movie wandering around Tuscany, and in the end they had a completely dreamy Tuscan wedding. We had just gotten engaged and hadn’t seriously started wedding planning, then. We sort of looked at each other and made a joke about it. “I want to have a wedding in Italy!” –> “Why not have a wedding in Italy?” –> “Should we have our wedding in Italy?” –> “Let’s get married in Italy!”

After we had seriously thought it over, we decided to move ahead with our Italy destination wedding because it fit with what we were looking for, and it was feasible.

We’d always wanted a smaller, more intimate wedding, and a destination wedding was perfect for that. We *loved* to travel. Italian food? Check. Italian wine? Check. Fabulous warm weather. Check. We couldn’t have imagined a more romantic-meets-old-world-charm location.

Logistically, Italy worked out well as a destination, as many of our friends and family would have had to fly in for our wedding anyway. We had family coming from Western Canada, California, Germany, Hong Kong. In fact, Daniel’s German relatives ended up driving in for our wedding from Germany.

Did you consider any other destinations?

Once we were inspired to have a destination wedding, we knew that was what we wanted. However, we did do some research about destinations weddings in other countries as well.

We were both drawn to the old-world romance and warm weather of southern Europe, and looked at Spain, France, and Greece as well in addition to Italy. Ultimately, we had just traveled to Greece at the time. We found wedding venues in France more expensive. And having been to Italy before, it didn’t feel as daunting as planning a wedding in Spain.

We didn’t have the budget for it, but for fun, we also looked at more exotic locations, such as the Maldives and Bali.

What was your Italy destination wedding itinerary like?

At the time, we were both early in our careers and were only able to reasonably take a little over a week off. (I would have liked to take 2!)

We had our wedding on a Sunday. Our red-eye flight landed Friday morning, so we would have 2 days to prepare for our wedding. We were tired and there was little time to relax before the wedding, but it gave us enough time to do what we needed to do and get over some jet lag.

We had our guests arrive the day before our wedding, and in the evening, had a welcome pizza dinner.

Our wedding lasted the entire Sunday. We had a Chinese tea ceremony in the morning, then the first look photography followed by the ceremony early afternoon. Afterward, we had a long aperitif and some group photos. We had a second photo session during golden hour, before the first dance and reception dinner. We did not exactly plan for dancing (we didn’t expect a wild party with 27 guests!) but there was dancing that lasted long into the night!

The day after our wedding, we organized an optional, causal outing into the town of Siena. After that, our guests dispersed to do their own traveling, and we spent the rest of the week at the villa enjoying a relaxing “honeymoon”.

How did you make your guest list?

We took a look at our accommodations (which we covered) and our budget and came up with an estimate of how many guests we could reasonably invite. In the end, we had 27 guests, plus the two of us.

It was important for us to have our family attend the wedding, so we started with that. We have small families on both sides, so it only came up to a dozen guests. We also invited close friends – eg. friends we had grown up with, our roommates through school, friends we travel with. Importantly, we made sure we included a plus-one for all our guests, in case they didn’t want to travel solo.

Unfortunately, we were not able to invite larger groups or school or work friends. But because we were going abroad, I think everyone understood, and there was no drama at feeling left out.

What goes into picking a venue?

We found this was the trickiest part of planning a destination wedding. The hardest part was not being able to see the venue beforehand.

Because of the rom com we watched, it was pretty cemented in our heads we wanted to be married somewhere in Tuscany, surrounded by fields and vineyards and old stone farmhouses. But there are plenty of gorgeous locations across Italy to choose from. We were definitely tempted by dreamy Lake Como and the beautiful Amalfi coast.

Even within Tuscany, there was an overwhelming number of options. From villas to castles and everything in between. What we found helpful was scoping out the previous destination weddings on our wedding photographer’s page. It gave us a great sense of the mood we wanted.

Our top considerations when choosing the venue was being able to have our entire wedding and stay in one place, good food, and reasonable budget. Most of our guests did not have access to a car, and we didn’t want guests to be scrambling from ceremony to reception to hotel. It was also nice for the guests to be able to relax and chill between the ceremony and reception. We ended up choosing Borgo Il Poggiaccio, a hotel converted from a medieval village. This hotel was within our budget. The on-site restaurant had excellent reviews, and there were several areas on the grounds that could potential host wedding ceremonies. We were looking for old world charm, and we could not have found anything better.

How did you pick your vendors?

Because photography and capturing our Italy destination wedding was one of our priorities, we found our wedding photographer first. We found Jules Photographer from searching on Google, and were completely blown away by his work. He captured the essence of an Italian wedding just perfectly.

The good thing about destination weddings is the vendors tend to know each other and work together. If we had known at the time how things worked, we could have essentially hired Jules to put together an entire team, from wedding planners to hair and makeup. However, as the destination wedding industry is not that big, it is also important to keep in mind sometimes you will run into situations where wedding vendors will *not* be happy to work together due to prior experiences. If you are set on one vendor or another, you might need to find an alternative. (It initially happened to us, but conflict was quickly adverted as we selected another option.)

For a destination wedding, we think a wedding planner is key. (Ours has since retired from the industry, so we are not linking her.) She was fantastic – she found our musicians, florists, and stylists. You don’t have as much control this way, but it’s way less stressful when you aren’t faced with unlimited options. I imagine it would have been nearly impossible to find our own vendors when you’re planning from abroad, especially when some don’t speak English.

What was the budget breakdown for your Italy destination wedding?

All in all, the cost of our wedding was around $25 000 (CAN).

By far, the most expensive aspect of the wedding was accommodations for ourselves and our guests. We did not book out the entire villa, but paid for “apartments” for ours guests for 3-4 nights, depending on their travel plans. We also booked an apartment for ourselves for the entire week. In total, this cost us around 7000 CAD. This was back in 2013, but looking online, the hotel prices have not changed all that much.

In terms of catering, done entirely by the hotel, it cost around 150 CAD per guest, which for us totalled around 4000 CAD. (This included a welcome pizza dinner, the wedding reception, and the aperitif. Unlimited wine included!)

Photography was approximately 3000 CAD.

We spent about 5500 CAD with our wedding planner, including her fees, decor (including chairs, tablecloths), favours, and hair and makeup. Of that, the florist was 2500 CAD. Music, including a harpist for the ceremony, a string quartet during the reception, and the sound system rental was around 1500 CAD.

How much planning did you have to do?

Planning a destination wedding is more thinking, and less doing. You can’t make as much DIY, nor focus on as many of the details. As mentioned above, our wedding planner found most of our vendors and took care of most of the details. We still kept Pinterest boards, and sent our planner details regarding the decor and vibe we wanted. Our hotel host planned the spaces and organized the meals. Our planner and host even got together ahead of time to go over the equipment and wedding day details.

However, you do have more logistical gymnastics to do. It was a challenge to find a venue without laying eyes on it and still coordinate an entire wedding weekend. Forget table chart, we even had to figure out who was staying in an apartment with whom!

We did made our own stationary, and arranged some of the details such as wedding parasols for guests. Anything we ordered, we had delivered directly to our wedding planner.

What was the most difficult part of planning for the wedding?

By far, we found the most challenging part of planning for our Italy destination wedding was never getting the full picture until we actually got there. We had no idea what our venue looked like, what the grounds looked like, until we were physical there 2 days before the wedding. The first time I saw the floral arrangements was when I was walking down the aisle, and then again entering the restaurant for the reception. (The good news is both times I was completely blown away.) Our photographer had scoped out the area ahead of time, but there were times we were literally driving around the countryside looking for the best scenery and the best lighting. (We were spoiled for choice.)

This all ended up working out for the better – at every turn, I felt surprised at how the wedding had come together and exceeded expectations. But you need a strong sense of trust and faith that you have planned hard enough and everything will just fall into place. Some things for sure will not, but you just need to let go and roll with it.

Is there anything you overlooked in the planning process?

The small things: having to haul a wedding dress on a plane and to a destination. (There were so many little things about the wedding dress I didn’t consider ahead of time. How to bustle it, whether we could manage our choreographed first dance…) We didn’t consider this until we have actually brought home the dress. We’d heard horror stories about brides walking away with the wrong dress or the dress being woefully damaged during the flight. There was also the option to have the dress professionally packed in a box (but $$). In the end, I simply took the dress in a carry on garment bag, and luckily it was a material that did not wrinkle on the overhead compartment!

Transportation was the most difficult issue we had. We thought we’d picked a venue that was relatively close to public transportation. It was – only 20 minutes away from Siena. Most of our guests flew into Rome or Florence, and took the train or bus into Siena. However, it still meant we had to drive into the city 5-6 times, including through the welcome dinner. It was a challenge to navigate the traffic while we located the train and bus stops!

Furthermore, our Borgo was in the countryside, with winding roads that are nearly impossible to find in the dark. Daniel’s relatives driving in from Germany almost didn’t make it to the wedding!

Did anything go wrong?

Nothing huge! The day went as smoothly as we could have hoped. It was a gorgeous day – but it could easily have rained, and we might have had to have our ceremony *in* one of the hotel rooms/apartments themselves. Vendors might not have followed through, or the final wedding might have been completely different from our vision. I think we kind of had to cross our fingers and hope for the best.

There are some things we had to change on the spot. For example, we’d planned to have the reception outdoors on the patio. We even had string lights delivered for the evening! Unfortunately, the late September night was too chilly. While we were making the best of golden hour and taking photos, our planner and staff move the wedding table indoors, and re-arranged the decor. (This ended up being even better than dining outdoors. All the flowers in the smaller space, the stone walls and archways and chandeliers – it all came together in a breathtaking way and created an intimate atmosphere. So sometimes… I guess fate knows best. :P)

We were not able to have a dress rehearsal, of course. Although we had a general schedule, our wedding was also our trial run! For example, our ceremony ended up being shorter than expected. There was a few minutes of complete confusion while our photographer and planner had to figure out where the aperitif was going to be set up, and the rest of us milled about.

Ultimately, there was nothing that affected our day.

What was your favourite part of the wedding?

We can’t mention our wedding in Italy without mentioning the *food*. We had an amazing aperitif spread that ruined charcuterie boards for me forever. For our reception, we had an out-of-this-world 5 course meal, and the most delicious millefoglie wedding cake in the world.

Our absolute favourite part of the wedding was getting to spend time together, just the two of us (and our photographer). We snuck away twice during the wedding, once after the “first look” to a small Italian town, and once before the reception into the Tuscan countryside. Even though we were technically taking photos, we really did get time to just walk hand-in-hand, enjoying the day and each other’s company. The wedding day can sometimes be chaotic, and we feel lucky that we were able to cherish what was truly important about the day – each other.

At the same time, we loved getting to celebrate with our family and closest friends. Everyone pitched in to make things work, everyone made speeches during dinner, everyone danced into the night. It felt like we got the benefit of eloping, with the benefit of throwing a party.

* The rom com was Letters to Juliet!