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When Mat proposed, he made the mistake of gifting me a wedding planning binder as a “gag-gift”.

Much to my delight, the 5-hour drive from the place he proposed in Montreal to our home in Toronto meant that I had his UNDIVIDED attention focused on myself and the binder for the WHOLE ride (muahahaha)! As you would expect, I held my husband hostage we used that time to discuss the most important aspects when starting to plan – the when and the where.

Let me back up for a minute. Mat and I traveled overseas together for the first time in 2012. I had left myself a month between quitting my old job and starting a new one, so we had the entire month of October to play! We booked a flight to Athens via a few days in Paris, and then booked a cruise out of Crete that took us to beautiful places like Rhodes, Alanya (Turkey) and Ashdod (Israel). It was one of those incredible, make-or-break experiences that solidified our relationship. While we were in Athens, we stayed at Mat’s family home in Loutsa/Artemida, which is about a 20 minute drive from the Athens airport and only blocks from the sea. When we went for a walk, we found the spot where Mat’s brother had proposed, close to a small Greek Orthodox church that his grandmother used to attend. I took one look at this church and knew it was The One.

Location settled.

The date wasn’t important to us, but I thought that if we could book something over the July 1st long weekend, more people would likely be able to swing the vacation time.

Simple, right?

In this blog series, I will go through some of the challenges that I faced while planning for and booking an off-the-beaten-path destination wedding, starting with the major pros and cons.

Destination Greece


  1. It is a trip you and your friends will never forget

I swear this was the best and most exhausting trip of my life. I have never traveled with friends before (or family, really – I am usually a lone wolf!) so having my in-laws meet us at the airport on the other side and taking some of our closest friends to visit the Acropolis was unforgettable.

  1. Your friends and family have an opportunity to bond

My dad, Matron of Honour, and her husband were all invited to another attendee’s wedding this winter because they had gotten to know each other so well over beers in the hotel. The connections you make with other travelers can be incredible.

  1. The location is unique to you

Nobody I know has been married there, and nobody I know will (likely) ever get married there. It’s our place. And that’s pretty cool.

  1. Less expensive (for the couple)

Our wedding budget got a serious boost, despite the fact that we were paying in Euros! Greek food is some of the best in the world, and we were totally spoiled with a great spread for much less than a Canadian restaurant or banquet hall. Bonus! We ate, drank and danced the night away poolside in a beautiful foreign country by the sea.

Destination Greece


  1. Don’t expect many of your friends to make it all that way

We had a grand total of approximately 45-50 people at the wedding, and honestly, I would never want to do a wedding larger! It was perfect and we were able to spend time with everyone. So, pros and cons to this one!

  1. You will probably need a translator

All I can say is thank God for my father in law. Without him, we might not have had any flowers at all.

  1. You will learn about different cultural customs (sometimes the hard way)

Greeks aren’t big on contracts a year in advance. It made for a couple nail-biter situations, but overall worked out fine.

  1. You have to spend time at your destination planning (rather than playing)

We arrived 2 weeks early so that we could spend a week planning last minute details (you know, like a menu, flowers, getting my dress pressed, putting together welcome bags, sorting out details with the hotel and the Priest…the little things!) and spend a week welcoming guests and showing them around.

Destination Greece

The Verdict

Worth it? ABSOLUTELY. It was worth sitting through conversations in Greek, treks into Athens in 40 degree heat looking for ribbon, and 3 attempts to buy flowers. It was worth it for all of the beautiful photos, memories, and inside jokes we now have forever.

Destination Greece

(A word to the wise: Don’t turn the wrong way down a one-way street when picking your father up from the airport after a 10-hour flight. He won’t appreciate it.)

(all photos courtesy of Anna Roussos)

Rachael Matheson-Dagonas – Managing Editor, She Sees The World

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