Get to Know Sailing Guide Gregory Heroux

Gregory Heroux is most at home on the water. He’s sailed across the Atlantic Ocean twice — one of those times during hurricane season. So when he returned home to Thunder Bay after 15 years of travelling the globe, he decided to make a living doing what he loves most: sailing. He started Sail Superior in 2000 with his father and has been sailing the big waves of Lake Superior — the world’s largest freshwater lake — ever since. He offers everything from 90-minute tours to daylong island excursions and multi-day customized trips, as well as sailing lessons.
How did you get into your field of expertise?
I live on Lake Superior, the largest freshwater lake (in the world). I went down to the lake one day with my father when I was quite young, and I looked at a sign that said: “From here it’s 2,000 miles to the Atlantic Ocean.” I was always intrigued by water and sailboats. When I was 10 (my father) bought a sailboat and it just became a part of what my dad and I did. We sailed, we dreamed of sailing the world, just kind of a dad and son thing.

How did you make the transition to becoming a tour guide?
I travelled the world doing many different things, and when I was about 35 or so I moved back to town to raise my daughter. When I did, I thought, “If I’m going to be here in this town, I’m going to invest in a larger sailboat.” So I went out with my father and we partnered up and started a sailing business. I had been travelling the world but I always had the sailing part of it with me, whether it was Australia or Greece or Japan or Finland. Wherever I went I would always go for rides and go to boat factories because I knew I wanted one, it was just a question of when. I do guide people out on the water (but) it’s more dimensional than that. … I’m a guide at a different level because I’m also your mode of transportation and your safety. Guiding is not how I really describe what I am — I’m more of a captain and I teach sailing.

What does a typical day look like for you?
Some just want to go on a really basic tour — we get on the boat, we go for 90 minutes, we talk about the city, we talk about the lighthouses, we talk about the water. I have to gauge whether they’re there because they want to be left in peace and enjoy the water and the sound of the waves and the air moving through the sails, and others that say, “I want you to tell me about the city” and we could be on a motorboat or on a coach. Sometimes people drop in or phone in the morning, other times we’re going out for three or four days and (they) want to go fishing, (they) want to go see some (Finnish) saunas, so I’ll put that program together for them.

Do you have a certain style of guiding, or do you just run with it on the day?
My style is very relaxed; I don’t have a program. When I go out there it’s not like I’ve got to get through these 30 things today. It’s a lifestyle for me and I try to show that lifestyle, (although) the 90-minute (trips) are more structured.

What is the best part of your job?
It’s the reaction of the people. If a big wave hits or a gust of wind comes and the boat heels on its side a bit and they all look at me — if I’m smiling then they start smiling. It’s a really nice feeling to be able to pass on my confidence to them so they enjoy themselves. At the end of the day, when they come off the boat and say, “I’ve never really experienced sailing but I loved that,” this is a really, really good thing. That’s what I really give people more than a tour.

What’s the most bizarre experience you’ve had on a guided tour?
It was a very windy night and we were watching the local races and people were saying, “Don’t those boats heel over?” and I said, “No they can’t,” and I spent about five minutes telling them all about this and I made them feel very comfortable. We were watching this one boat and it had a manufacturer’s defect and it actually broke its keel and it falls over and they look at me like you’re full of s—. That was about the funniest thing (that ever happened).

Ever had any odd requests from clients?
I took a group out sailing and it rained and blew hard and there was a bit of lightning and thunder, so at the end of this three-and-a-half-hour trip I said “I’ll give you a rain check or I’ll refund your money” and they looked at me like I had insulted them and they said, “Have you got any idea how thrilled we are to be out on Lake Superior in this storm?” So from that day on I’ve said you get what you get but it’s going to be an experience. It’s not an odd request, but for me it was odd that I thought they wanted something particular and they were willing to experience new things.

Every job has its ups and downs. Are there any aspects of your job that you don’t like or aren’t that keen on?
The part that is a little bit stressful is making people comfortable on a boat that is out of their comfort zone. The water is very cold, there are tripping hazards, there are lines and ropes, and I have to enforce that. I don’t want you to be frightened; I just want you to respect it. I’m really comfortable on a boat, I want you to be comfortable but I want you to take small steps. I’ve had some people who just get up and go, but in 14 years I’ve never had to (fetch anyone from the water). One of my lines is anybody who doesn’t listen to rule No. 1, which is to hang on to the boat, I’m going to have to treat you like my six-year-old and I’m going to have to yell at you.

As an experienced guide yourself, can you explain to our readers what the benefits of hiring a guide are?
I’ve travelled the world and I would have never hired a guide, but I was pretty stubborn. I was always one who investigated on my own and did my own thing. I’m probably one of the people I’d never want to have on my own boat. The advantage of hiring a guide, providing the guide has a reputation, is that you are going to get information that is very personal to you, it’s going to be relevant to what you’re doing and it’s going to enhance your experience. It can be (for) safety, but it can also be, “You don’t want to eat there, it’s overrated.”

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