Some smart musical theatre lyricist said to “start at the very beginning, a very good place to start.” But for today, let’s think of this as an editorial to capture the magic of a destination wedding in Santorini, Greece.
Here is my ode to the beautiful friends, food, architecture and faces of the island. What do you wear on a vacation that might include walking, hiking, shopping, lounging, swimming, riding around on a four-wheeler, a wedding and…. adventure? I think I got this one figured out. I had lots in my suitcase and felt ready for anything.

Oia’s Jenga-like architecture is every bit the post card you imagine – homes stacked precariously on top of one another, along the cliffs and hillsides. One person’s roof is another’s infinity pool.

The El Greco Hotel – the most amazing experience. The staff was just spectacular (see the “LOVE” story about our stray puppy resue). This was home base for the duration of our trip.

The Greek are very specific. Don’t do it. Do what? Don’t leave – is how we felt at the end of our trip.

We rented ATVs for two days and explored the entire island.


A shop in the traditional village of Megalochori.

Catching the sunset in Oia.

From the terrace of Kyprida (restaurant) we could see a pack of kittens playing in the setting sun on the roof top.

A burst of colour – the doors of Santorini were a favourite study for us. The tank and maxi skirt were a great choice in a breezy fabric, able to be tucked up for riding the ATV, but still comfortable for walking or dining. The cardigan was a must, to limit sun exposure on the shoulders. American Apparel jelly sandals let me go from town to beach, from the hot sand and straight into the water.


High waisted linen trousers and a cropped striped t-shirt, with Keds for walking all day and driving on the ATV.

A posh perch at Eros beach. We drove down a long, winding dirt road, with wind-carved cliffs on either side of us, which opened suddenly onto a picturesque beach with thatched umbrellas and a beach-side restaurant/bar.

Window shopping in Thira, Santorini. A ruffled, one shoulder dress in a bold print got me a compliment from a complete stranger. And an elderly Greek gentleman told me I had the look of a European ‘fashionista.’ I’ll take it.

Blue beads, headscarf (to save me from helmet hair), sunnies, navy blue culottes and a lace top, with comfortable shoes for walking all day! Plus a bucket back that fit nicely into the ‘trunk’ of the ATV.

A bright blue crop top and patterned maxi skirt, bold earrings and flip flops for drinks pool side.

The El Greco was simply – the loveliest, most welcoming resort. It was beautiful to look at and very luxurious, but that was the tip of the iceberg. The staff was just SO nice. They helped us at every turn, especially in finding a home for the sweet puppy we fell for.

Our little sweetheart, Gaia, stole our hearts. We got her microchipped, vaccinated and the hotel’s staff helped us to find her a home when we were unable to get the documents to take her back to Canada with us.

Perissa Beach, Santorini. Post-wedding day of recovery and relaxation.


Rehearsal dinner outfit: Black crop top with back cutouts, bow-belt and tea-length high waisted skirt with lace overlay.

Heading to one of the El Greco’s numerous salt water pools.

Happy Toronto Pride! We hit the airport, ready to wave our mini flag. This is the first Pride in 16 years that I’ve missed. For travel, you carry your hat (to save space), wear culottes in a wrinkle-free fabric, a tank for arrival and a patterned cardigan for the plane.

Allia is ready to hit the rolling sidewalk. Departures, in comfort and laid back style.

Last supper. Falafel, salad and pita.

Cucumber, dill, pine nuts and smoked salmon salad.

Our final meal was recommended by the owner of Muska, one of our favourite stores in Thira. The food was delish!

Wine tasting at Gavalas Winery.


Crazy beautiful. Monolithos Beach.

Incredible skies.


The view on the way to Oia for sunset.

The clouds and sunlight in this cemetery were so beautiful. Exploring and taking unexpected turns were some of the best parts of this trip. It was a ‘Say Yes’ vacation.

What do you expect to find at the end of a long, off-roading adventure? Definitely a mixed martial arts ring that looks like Mad-Max-Thunderdome fights happen in it under flood lights at night.

Chilling out max and relaxing all cool – at Eros beach with Elissa and Allia.

Sardines. Allia’s favourite. I always make ‘yuck’ face when she eats them at home. Only allowed because we were eating at a roof top terrace.


This car was so dusty that people had written messages from countries far and wide.

Journalling throughout the trip. Allia likes that I enjoy writing, because it means we get to look back at our trips and reminisce – in detail. Wink.


One of my favourite moments in Thira, at night, was seeing the gorgeous and uber-cool Elle Macpherson. She is stunning in person, and was so gracious about taking a photo even though she MUST have been bombarded 24/7. I was as close as I’ve ever been to star-struck. She is such an icon and I’ve just been re-watching Friends. It made my night!

I loved all the donkey iconography and sculptures – a day of wandering and night out for dinner requires a beautiful Anthropologie tie dyed dress with lower back cutout.

A bohemian mish-mash of patterns. Beach-side eating, al fresco, with swimsuits under tunics, at Waves Restaurant.

Love to love you, baby.


Plates to break at the Greek Wedding!

Picked up this Anthropologie dress, regularly $258, for $30. Paired with cork and gold heels, and some bling-y costume jewellery, it was perfect for dancing the night away. I thought about wearing something lighter, more beachy, but the weight and structure of this fabric actually held up really well to the mediterranean heat and humidity… and the dance party that lasted ’til 3 am. Allia also wore a cheap and cheerful Grecian inspired, red satin maxi dress with halter bared shoulders and a drawstring waist, and gold accents.

The ceremony and reception took place at Oceanides, right on the water with a pool and tables surrounded by the sea and candle light.

Hamming it up for the camera. The wedding was like a high school reunion (with the best possible outcome). Turns out the bride, Lindsday, stayed in touch with all the nicest, most sincere and warm people we went to school with. Catching up with them was amazing, as was meeting their new partners and families, and having them meet Allia.


Journaling, the morning of the wedding. Ready to do hair and make-up in a strapless ruffled dress with asymmetrical hem, and some bright beads.

Trip in reverse: Here is our first night. The rehearsal dinner. The couple pulled out all the stops and treated us to an incredible multiple course dinner – and we ate like royalty (see below for some of the highlights).


Truly back to the beginning. This is day one. We had no idea what an incredible trip we were in for! Thank you, Santorini, and big thanks to all the friends, new and old, who made this a wonderful week in paradise.