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How to plan a One of a Kind Wedding: A Conversation with Toronto based Wedding Planner Ashley Pigott

How many of you have spent countless hours building Pinterest boards, saving Instagram photos, and scrolling TikTok looking for that perfect tented or private estate wedding inspiration? Yeah, same here. Those are all incredible tools when looking to plan a one-of-a-kind, unique-to-you wedding. But we decided we would take it up a notch by reaching out to none other than one of Toronto’s premier wedding planners, Ashley Pigott, who specializes in curating  logistically challenging weddings.

Who is Ashley Pigott and why does 515 love her?

Ashley Pigott is a trailblazer, a tastemaker, and is an expert on tented and private estate weddings. As a highly sought-after Toronto and International wedding planner, she is known for her ability to make anything possible and everything breathtakingly beautiful. Throughout her 20-year career in high-end hospitality, including positions at luxury hotels and prestigious restaurants, Ashley has developed a reputation for expertly managing complex logistics and delivering flawless results. An industry leader, she immediately established herself as a tented and private estate wedding specialist. Since then, she has expanded her specialties to include multi-day, destination events that allow her to showcase her impeccable attention to detail. With a calm, compassionate presence, Ashley is the trusted planner for couples who want their wedding to feel elegant and effortless, down to the very last touch. Here’s what she had to say.

 

515: Hi Ash!

Ash: Hey guysss!! 

515: Okay, first things first. What led you to become one of Toronto’s most sought after Event Planners?

Ash: I started in restaurants and catering and eventually ended up in luxury hotels. Hospitality is at my core, luxury experience is my love language. My goal is to anticipate needs before they are needed. I fell in love with weddings, each being so unique and never the same. I was drawn to the unique design each event has and how each one will never be recreated. Take that and multiply it times 1 million and you get what I’ve grown into and the style of weddings we now curate.

515: What makes a wedding one of a kind? And how are you so good at pulling off these major, logistically challenging events?

Ash: First of all, thank you! I like to think of myself as a one-of-a kind wedding planner, for one-of-a-kind weddings. I offer my clients a custom experience. The way we plan together is curated around who the client is, what their interests are, and how they like to work. One of the first things I do is learn what’s important to my client, and then I am able to cater my process to their needs. If I know that my client loves nature, chances are their guests do too, and therefore a golf trip in Muskoka is going to be a lot more fun than a trip to the art gallery.

515: How many events do you take on a year? 

Ash:  I take on 8-10 weddings a year, and I try to stay around this number in order to allow myself to be fully involved in the process. And when I say weddings, I mean multi day weddings. We are not talking about a one day wedding at a gorgeous hotel. I am talking about the rehearsal dinner, welcome party, wedding day, farewell brunch, and all the moments in between, if that is what the client is looking for. I want my clients and their guests to experience a weekend unlike any other that they have before. We’re talking about high level, white glove service.

515: How much time do you spend planning a wedding?

Ash: The average amount of time pre wedding is one year to a year and a half. At the beginning we’ll have weekly meetings, then bi-weekly, then weekly again leading up to the weekend and wedding day. Like I said, I like to be very involved, and these multi-day events take a lot of time to make perfect.

515: What’s your biggest piece of advice you would give a couple planning these kind of events?

Ash: Start with your priorities and then determine what your overall investment into the wedding is. I don’t want to scare people away, but I love to talk about money. And it’s a necessary conversation to have at the beginning of the process. I love to ask the bride and groom separately (don’t worry this isn’t a relationship test) what their priorities for the weekend and wedding day are, because often they can be different. Is floral a priority? Is impeccable bar service, the menu, the cake, the dress? What are each person’s priorities and how can I make them all happen? From there I can take both sets of priorities and bring them to fruition and make them the pillars of the day.

515: Okay, let’s talk about tented weddings! As we all know, you are the queen of tented weddings, and we have shot so many of your gorgeous tented events over the years. What is your secret? 

Ash: Okay, first things first… let’s talk about Southern Ontario weather. Yes, tented weddings are absolutely beautiful, but they come with a level of risk. And what I need to ensure before proceeding with a tented wedding plan, is that the couple is okay with the level of risk involved. There has to be a rain plan. And the rain plan has to be so good that if it does rain (and sometimes it does) the couple will be just as excited as if it didn’t because of the excellent plans in place that they have been made aware of months in advance. And I say this with love, if you can’t handle the stress of a rain plan, then maybe a tented wedding isn’t for you – and that’s okay, because there are hundreds of other beautiful options out there waiting for you. Most of my clients already come to me knowing they want a tented wedding because logistically, I have done a lot of them and I have the expertise it takes to make sure my couples feel safe and trust that their big day will go off without a hitch. The thought is intimidating to them, but at this point, I am the expert, so leave it with me. 😉

515: What would be your dream wedding to plan?

Ash: Well, truthfully this year I achieved a huge bucket list destination wedding in Italy, and it was amazing! I would do it all over again. But now, if I’m dreaming big again, I would say it would be to be a snowy mountaintop wedding. Welcome Party is an apres ski vibe, perhaps at the Four Seasons in Whistler. Ceremony on top of the mountain followed by a reception. I would make it feel like a real life snow globe. After the ceremony we would go to the art gallery in Whistler for the reception. Dreamy & Delicious! No? 

515: Ummm yes, please sign me up.

Ash: Oh, you’ll be there! Second dream wedding to plan would be an epic tent on a ranch in the mountains. Huge open sky. Here’s the thing, just like a photographer, you can take a planner from Toronto and take them ANYWHERE. The geography of where someone is located doesn’t matter anymore. I love to use local vendors when I am in different places, but in my opinion, for key vendors, relationships should outweigh where they’re located.

515: We couldn’t agree more, see you on a snowy mountaintop, or in the middle of the countryside very soon! Manifestation!

So we have you convinced to take the leap and begin planning your one of a kind wedding yet?

While you continue to dream big, check out another one of our amazing tented weddings with Ashley HERE.

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