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Offshore sailor has an astonishingly badass résumé. She’s sailed around the world five times—twice solo and in each direction, including a 2006 voyage when she became the first woman to do it against the prevailing winds and currents. She is still the only woman to have sailed around the world non-stop three times.

Last year, she joined the all-women Team SCA during the 2016/17 . This month, she returns to the event as the only female skipper, and at the helm of a , which will start the 46,000-nautical-mile competition on October 22 and won’t finish until June 2018. We hopped on board with Caffari a few weeks before the race to talk training, why Wet Wipes are her most important piece of gear, and what life cooped up on a 65-foot boat for nine months straight is like.  

OUTSIDE: How did you get into offshore sailing?
DEE CAFFARI: I didn’t start as a sailor. I was a teacher. I changed careers after five years—I thought there’d be more longevity in yachting. 

The Volvo Ocean Race was always in the back of my mind because, for me, that was the pinnacle crewed, offshore, around-the-world race. In the last edition, there was an all-female team and I was not going to let an all-female team leave the dock without me on that boat. So I became part of Team SCA.

Why do you want to do the race again?
It’s one of those things where, once you learn what it’s all about, then you know you can do it better the next time around. I was applying to all the teams and I think everybody just assumed I was going to set up my own team. Then the Turn the Tide On Plastic project came together and I was asked to be skipper. 

What’s the message of the Turn the Tide On Plastic team?
We have a sustainability message. We’re educating people to be more aware of their use of single-use plastics, to reduce that consumption for the oceans’ health. We’ve got a strong diversity message, with 50/50 women and men, and some really young sailors. We want to give them opportunity to race with people at the highest level. And I’m the only female skipper in the race, which also plays into that messaging. 

Can you remember going into your first offshore race?
I went offshore for the first time as a skipper, so I was super stressed. I read a million books about it. I didn’t sleep because I was too scared. But you learn how to manage it.

What is life like offshore?
It sounds beautiful, you know, endless horizons and sunsets and sunrises, but the reality is you share your bed with another sweaty, salty sailor. Everyone’s feet start to smell. It will be wet and cold and hot and stuffy and sweaty—there’s very rarely any in-between. You don’t have a bathroom. Your toilet is outside, off the back of the boat.

How do you manage with no showers or fresh food?
Wet Wipes are your best friend. The food is freeze-dried—porridge for breakfast and then some sort of freeze-dried meal for lunch and dinner. You get a chocolate snack, because that’s quite good for morale, and then an energy bar, a protein bar, and dried fruit and nuts to snack on. We make water from the sea using a filter.  

When do you sleep?
We run a watch system—four hours on, four hours off. So the four hours that you’re on, you’re on deck trimming and making the boat go fast, then your four hours off includes eating and drinking, personal hygiene, and anything else that you need to do. Plus, of course sleeping. 

If there’s a maneuver or a sail change, you’re woken up to help. So in your four hours off, you probably get two hours’ sleep, on average. But some days you get more than that, so it all equals out at the end. 

Is the Southern Ocean as tough as it sounds?
I don’t know if everyone is tough enough to go through the South—it’s a miserable place if you're not enjoying it. If you love it, then it’s great. But you'll be wet and cold for a long time, and if that’s not really your thing, then you’re in trouble. 

I personally love it. I’m really pleased that the race is going back there—it’s true, proper sailing. I get a real buzz out there, where I feel like I”m sending it for days on end. It’s ridiculously fast, it’s ridiculously wet, and ridiculously cool sailing. That’s what we sign up for.

What are the challenges you face?
The whole race, the elements out there, are a challenge. How we manage ourselves, through, that’s what’s key. Doing well in the race is about making the least mistakes and sailing the boat fast. 

My main fears are illness and injury. You want to keep everybody safe and able to perform at their best. I’m excited and nervous, but I’m always nervous at the beginning of a race. It’s anticipation, adrenalin.

What do you miss about life on shore when you’re on the boat? 
I always miss my dog, Jack. You live in a lot of random places when you’re offshore and you miss the familiarity of home—be it a carpet or a sofa. With the Volvo, we stop a lot, which means I don’t miss as much. 

What’s the longest time you’ve been offshore?
When I went the wrong way around the world! I was offshore for six months and I missed a lot. I missed carpet, I missed sofas, I missed tea in a china mug. I missed fresh fruit.

Also, as an aside, it was quite funny to go back to driving after that much time on the water. The cars all felt really close to one another—I’d been so used to open ocean and loads and loads of space. Everyone was driving so fast. 

Do you have to crazy to be an offshore sailor?
I think it helps. There’s nothing really sane about being fire-hosed on the deck for four hours at a time, then going below and trying to sleep, then getting up and doing it all over again. But we all love it and we keep coming back.