At sea: life on the water with Intrepid skipper Mike Simon

written by Justin Meneguzzi October 16, 2017

‘Do you know where we’re going?’. It’s the most common question Mike Simon gets as a skipper, and it’s the one that always makes him chuckle. I can see why.

Mike has just navigated through a storm back to port, steering a course all night as waves rocked our little catamaran in the Gulf of Mexico. He doesn’t need to say it but the look on his sun-kissed face tells me it’s been a long night. Safely back at shore, Mike takes a considered drag on his morning cigarette before telling me in a charming Wisconsin drawl that sailing is in his blood.

‘I grew up in a boating family on an island in Lake Superior, and I started racing sailboats during my teens. For the last nearly 10 years, I’ve held my United States Coast Guard credentials and have been running charters and teaching people how to sail ever since.’

Mike and passengers learning how to tie knots.

Mike shows us some important knot techniques.

He’s not quite an old salt yet, but the lines of a life with plenty of water and sunshine are beginning to show. Mike’s spent most of his career sailing across inland lakes and coastal waters and, while he’s never lost a person at sea (a personal point of pride), he has seen some hairy situations.

‘I was in a sailing race and, due to very strong winds, I got launched off of our 18-foot racing boat and ended up floating in the Gulf of Mexico for an hour, by myself. In 10 to 12-foot swells, it can be very hard to find and rescue somebody floating out there all by themselves.’

It’s not a stunt that’s been repeated on Mike’s leisure charters and he’s quick to put nervous sailors at ease. He says a certain level of apprehension is natural and healthy, and a curiosity to learn about the boat can help settle your nerves. Sailing also means embracing the unpredictable nature of the sea, and the possibility of a little seasickness. If you’re anxious about seasickness, Mike’s best advice is to prepare for it.


‘It’s nearly impossible to know what the weather is going to be when you book a trip, but there are some great products and medications that help. A lot of times being outside and feeling the breeze on your face will do a lot to ease your queasiness. I am lucky that I haven’t been seasick yet – but I do get land sick because you miss that swaying feeling.’

When the conversation turns from the health of his passengers to the health of the ocean, Mike’s usually laid-back demeanour hardens. As a man who gets to see the best of the outdoors every day – spotting manta rays, sea turtles and pods of dolphins slipping in and out of the water is all in a day’s work – Mike is passionate about sustainable travel, and he says the amount of rubbish he finds in the ocean is sickening.

Three passengers and Mike aboard the boat.

On board the catamaran.

‘Being on a sailboat forces you to really think about what you’re using. Every boat has a limited supply of electricity and fresh water, which means you need to be conscious of what you’re doing. I like to think people who sail with me take this awareness back home and apply it to their everyday life too.’

Mike says one of the things he loves most about his job is the people he gets to meet, but he also enjoys witnessing the interactions between his guests, who have sometimes come from around the world to be on his humble boat.

‘I think it’s very important to travel, because it takes away some of the misconceptions people have. It lets you see that we’re all on this floating rock together and share so many earthy qualities. You realise we’re all different, but all kind of the same too.’


Not surprisingly, Mike’s own foray into travel was on a Caribbean cruise with his parents when he was a kid, but he’s since had the chance to explore Japan (which he’d return to in a heartbeat) and China. If money were no object, he’d pack up his boat and sail around the world, stopping at the Galapagos Islands, cruising the Amalfi Coast and dropping into Tokyo for ramen and a cold beer.

For now, though, Mike tells me it’s the simple things that keep him buoyed: the sunrises and sunsets, and knowing precisely where to point his compass.

Make like Mike and jump aboard an Intrepid sailing adventure.

Featured image by Ben McNamara.

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