How To Plan a Destination Wedding in 7 Stress-Free Steps

What happens when a travel-obsessed girl meets an Italian guy and they decide to make it official?

Well, my partner and I are planning a destination wedding celebration in Italy. Not because we want to be fancy, but because half the guest list is already there.

There’s my Mario, who is, as you may have guessed, very Italian. (We met quite randomly when he moved to Toronto for work.) He was born and raised in Piombino – a lovely Tuscan town with gorgeous ocean views and incredible food. His family and close friends are all there, with a few closer to Rome in Civitavecchia.

Coincidentally, I have relatives on my mother’s side who are only about 90 minutes away, near Lucca. My immediate family, however, will be coming all the way from New Zealand.

Then there are guests flying in from Canada and other parts of the world.

For many this will be not only a destination wedding, but a chance to experience Italy.

A lot is on us to plan accordingly so that everyone has a great time. No pressure, right?

Luckily time is on our side with T-minus about two years. To make the most of this window and get my planning checklist in order, I got a little help from travel expert Taylor L. Cole.


1. Start. Planning. Now.

“If you want friends and family to travel long distances to attend your wedding in a faraway destination, give them ample time to save up and go,” says Cole. “Planning these sorts of events bring another level of complexity, requiring extra time to smooth out any wrinkles that might happen along the way.”

Check. Our plan is to present an information package to all prospective guests by the spring of 2017. This will include how to get there, accommodation options, what to expect from this particular area of Italy, and other details that serve to sweeten the deal.

This way, our international arrivals can prepare and budget accordingly (many have small kids) and no one can tell us we didn’t provide enough notice. A year and a half should be sufficient, yes? And lots of time to perfect those common phrases via Duolingo.

 2. Research Rules “Streamline your research to meet your specific needs and budget.” Check. For us, this is a crucial part of the puzzle and the biggest challenge. With all the venue options under the Tuscan sun, how the heck does a girl choose? Add the budget range of our guests and things start to get complicated. My 2016 solution to this 2018 conundrum is to focus on finding one amazing venue that guests have the choice of either staying at or nearby in another hotel or Airbnb. That said, we do feel it is our responsibility to suggest a variety of budget-conscious options that will successfully accommodate both those within driving distance and those flying in.

BUONGIORNO . . . The views on my morning run are hard to beat ?☀? . . . #Piombino #Tuscany #Italy #nofilter

A photo posted by Sara Graham (@freshpresse) on

3. Scout It Out

Obviously, this goes hand in hand with research. Cole states that “you will need to scout out the destination where you want to marry and spend some time in the hotel or resort in order to meet the people who run the place. Maybe even scheduling your trip so that you can peek in on someone else’s wedding while you are there. Having a look around will give you an idea of what guests can do before and after the wedding celebrations.”

Check. With all the incredible regions and their Instagram eye candy, we are thankful to be bound, by practicality, to Tuscany. And then the venue will have to be close enough to Piombino so Mario’s friends and family can simply taxi there and back.

Since recent trips have afforded us opportunities to do some pre-scouting, we are assessing here and here as venue options.

PIOMBINO . . . The week starts here ☀????
#Tuscany #Italy

A photo posted by Sara Graham (@freshpresse) on

4. Call An Expert (or Phone A Friend) “Many hotels that cater to destination weddings offer couples the help of a wedding planner,” says Cole. “Take advantage of these experts, even if it costs you more. They can help plan for every eventuality and will make the entire planning process a lot less stressful. If the destination doesn’t have such a service, see if there is an independent consultant for hire in the area.” Check. Luckily Mario’s best friend Federico would be a top candidate for Mayor of Piombino if he were actually running for the position. Which is to say he knows everyone, including the owners of both venues under serious consideration. Furthermore, he takes good food seriously and we trust his taste implicitly. His own wedding was just four years ago so he is as good as any pro consultant.

PETRA . . . Vino meets architecture meets landscape ??? . . . #Tuscany #Toscana #Italy

A photo posted by Sara Graham (@freshpresse) on

5. Speak Easy

A pretty major concern for me is bridging the gap for those who only speak English and those who only speak Italian. I started with the possibility of hiring translators to mingle through the main event, but have landed on the more practical strategy of engaging our bilingual guests. Positioning them within groups to enable conversation. This extends to table settings, as well as side events like a tour of Petra winery, and visiting Populonia as well as other centuries-old communes.

Of course, these bilingual boys and babes will be rewarded with special gifts. Well worth it as they will play a key role in enhancing the whole Italian experience… La dolce vita like a local!

6. Legalese “Be aware of the legalities of getting married in a foreign country and what that means to your marriage status back home,” notes Cole “Make sure all of your paperwork is in order so that there are no surprises. Also be aware of laws about bringing in foreign contractors to work for your wedding. such as photographers or DJs. They may not be allowed to work in the jurisdiction you are getting married without special visas.” Check. Noted and all points are on the list!

7. Control The List

“More often than not, a destination wedding is a big financial commitment for your guests,” says Cole. “Invite only your nearest and dearest to attend. For everyone else, plan a less formal party when you get home.”

Check and check. As with most weddings, the venue dictates the number of people so we’re waiting to determine a comfortable capacity before making our Italian guest list. For those that can’t make it, we will defer to small soirees when Mario and I can go to them.

Clearly, a wedding in another country has its challenges and is something you really have to want. (Unless you’re doing it a la Kimye and have someone else to plough through the planning.) However, I have no doubt the rewards will be many and memorable.

For inspiration, picture yourself getting hitched in one of the top 16 dreamiest wedding destinations according to

  • Aruba
  • Belize
  • Cancun & Riviera Maya, Mexico
  • Costa Rica
  • Dominican Republic
  • Florida Keys
  • Fort Lauderdale, Florida
  • Italy
  • Jamaica
  • Los Cabos, Mexico
  • Napa, California
  • Oahu, Hawaii
  • Puerto Rico
  • St. Kitts
  • St. Lucia
  • Turks & Caicos