Photo: William Gayle

Mike Simpson, is a man of missions. He’s paddled up the East Coast, over 2,000 miles from Florida to Maine in support of the Wounded Warriors Project. He’s done 420 miles (with 10-12 portages) on the Connecticut River from the Canadian border to the Long Island Sound. He’s navigated his standup the entirety of the intricate and island-riddled coast of his home state, Rhode Island. And he’s hauled down the Big Sur coast from the town of Big Sur to Cayucos in big seas. Now Simpson, 44, has his sights set on circumnavigating Puerto Rico. SUP magazine will be meeting up with Simpson to document part of his journey for the print edition. We caught up with him as he readies himself for his epic journey.

How are things going?
Well, it's not an adventure until things go wrong. I’m on the ground in Puerto Rico now but there are hiccups with shipping company and I’m having problems getting my board from what I call ‘prison’. I'm gonna bail her out on Monday. Before we leave I’m having a friend from the south side put in a fin box.
But I went for a paddle yesterday in town and we're going to try and chase some waves down this weekend. I’m still in the process of down-shifting from uptight East Coast mode to laid back Puerto Rico.

Photo: William Gayle

What makes this mission different than your others?
I think it's the unknown. I think SUPing this style is really heady, it's mental. I've paddled enough on the North Shore of Puerto Rico to know about the reef passes that pop up in front of you and you have to go inside or outside of them. I also know there will be a 114 mile upwind section of the trip. The Puerto Ricans tell me to do the north side then drive back and do the south side so I don’t have to do the upwind. But from my backcountry skiing and backcountry camping, I figure it's part of the whole thing. You’re taking what Mother Nature's giving you and getting it done. I know I'll be going up wind and I'm fine with it. That expectation makes it easier. Then there’s the self supported part of it: I don't know where I'm sleeping but I have general ideas on the chart. But on a trip like this there are angels everywhere. You think you're having a horrible day and you pull into the beach and a fisherman invites you up to his house for dinner or points you to a better beach around the corner. I like the unknown.

Why Puerto Rico?
Last winter I came down here a couple times, once for Paddle Royale and once after. I fell in love with Puerto Rico and met a bunch of people that took me under their wing. I came back later for another month and surfed and paddled. It's a perfect square and isn't that big and I just thought I should paddle around it. It was really wanting to see this island nice and slow just like the ancients would, no itinerary, carrying all my gear. There are beautiful places that people never get to see.

Photo: Benjamin Thouard

Tell me about your board.
When I brought it up to Patrice, our shaper at BIC, he said lets shape a board for it. We sat down at Outdoor Retailer last August and we came up with a beautiful 17.5-foot design. The unique part about it is Patrice shaping a board this size. He hadn’t really stepped into that realm before. He liked the board so much he shaped one for himself. He didn't change anything. This board has plugs for strapping and we've put texture on the deck and scalloped out the deck so my bags sit a little bit lower and don't slide when I get hit by waves. That's huge. I can't tell you how many times I've had to stop to rearrange bags. I also went a little bit wider; I'd rather have stability so I’m not as fatigued and can take a little bit more weight. I was shocked by the stability. I don't want to be in the water.

How does it downwind?
It's awesome. I was riding bumps, two-foot or three-foot only, but it was effortless. I was really, really stoked. It's a tucked in pintail and it picks up every little bump. Getting used to the rudder, which we’re prototyping, is a little difficult. I’m also having a friend on the south side put a fin box in case the rudder fails.

So you’ll be camping the whole time?
Yep. I have a hammock, tarp, bug net and total lightweight sleeping back. Usually I sleep in a hammock on a trip like this. I did that the entire 2,000 miles and four months when my buddy Will Rich and I did SUP The Coast from Key West (Florida) to Portland (Maine).

Well, we’re stoked to get on the water with you.
Me too. Looking forward to it. Time for me to go paddle and then chase some waves.