Sailing Holidays VS Race Sailing: Going Extreme

Törn vs. Regatta - Urlaub gegen Sport

Meet the famous race sailors who take sailing, as we know it, to the next level.

We love sailing holidays.

Relaxing on a gorgeous beach with the wind in your hair and a cocktail in hand is our kind of sailing.

We love island hopping and gliding through the azure waters of the Mediterranean, devouring local cuisine and watching glowing orange sunsets.

We love to lie back on the warm deck of a beautiful, glistening yacht and work on our tans.

But race sailing is something totally out of this world.

Race sailors are the people who really know how to sail. They take sailing seriously, they’ve developed a life-long passion for it and they know how to rule the seas.

Competitive sailing is a fast, demanding and dangerous sport, and it takes a lot of skill and a lot of muscle to fight the crazy swells and wind patterns of the ocean.

We really admire these fierce sailors, so we’ve put together an introduction to four of our favourites.

Check out these famous competitive sailors and their crazy sailing stories.


Ben Ainslie

Ben Ainslie sailing Zizoo

Ben Ainslie – or rather, Sir Charles Benedict Ainslie – is an English competitive sailor and the most successful sailor in Olympic history. Over the period of five separate Olympic Games sails, he won medals at each one, making him the first person ever to win medals at five separate Olympic Games. He was also the second person to win four gold medals in the sport. Ainslie also competed several times in America’s Cup, and in 2013 formed Ben Ainslie Racing, with the goal of producing a British team to compete in the challenging race. Ainslie started sailing at just eight years old, and began competing at the age of 10.

Ainslie quoted to the RYA, “That was one of the scariest races I have ever had to go through, the wind was all over the place making it very very difficult. I stuck to it and did the job – it’s just an amazing feeling and I can’t thank everyone enough who has helped me over the years to get to this point.”

Emma Pontin

Emma PontinEmma Pontin







Lawyer-turned-sailor Emma Pontin is one strong woman. Despite a long battle with breast cancer and a double mastectomy in 2007, she refused to give up sailing. Battling with the wind and swell helped her get through her battle with cancer. Her sailing achievements include a round-the-world-race and several transatlantic crossings. Pontin was sadly diagnosed with cancer in 2006 as she was about to embark on a race and was forced to withdraw. But in 2011, she embarked on a year-long round-the-world voyage with 42 other men and women who have suffered from breast cancer.

Pontin told CNN in an interview, “I want to tell this people: ‘Do something amazing, cross an ocean, bring it on!”

Web Chiles

Webb Chiles

Webb Chiles is an American sailor, poet and explorer, who has circumnavigated the globe five times and achieved several world records. Now in his ’70s (and on his 6th marriage!), Chiles is not done yet. He is planning yet another circumnavigation on his Moore 24 called Gannet. Growing up, he lived on his boat and taught himself how to sail and navigate in the six years leading up to his first solo circumnavigation during 1975 – 1976. He has also authored several books and published hundreds of articles and poems.

On his website, Chiles introduces himself in this way: “People who know of me at all probably do so as a sailor; but I have always thought of myself as an artist, and I believe that the artist’s defining responsibility is to go to the edge of human experience and send back reports. Here are my reports.”

Jessica Watson

Jessica Watson sailing Zizoo

Jessica Watson holds the record for being the youngest sailor to travel solo and unassisted on a non-stop sail around the world. She earned this title in May of 2010 when she returned to port in Sydney, Australia, after seven months circumnavigating the souther hemisphere. She was only 16 years old when she completed her voyage. In 2011, she was named the Young Australian of the Year, and she continues to sail the seas in races like the challenging Sydney to Hobart.

The Los Angeles Times interviewed Watson about her reason for her journey, and she said: “I wanted to challenge myself and achieve something to be proud of. And yes, I wanted to inspire people. I hated being judged by my appearance and other people’s expectations of what a ‘little girl’ was capable of. It’s no longer just my dream or voyage. Every milestone out here isn’t just my achievement, but an achievement for everyone who has put so much time and effort into helping getting me here.”


So, while we lie back on our comfortable yachts and glide peacefully through calm, turquoise waters, we will think of these incredible yachtsmen and women and their courageous battles with the sea.

Of course, there’s always the chance to pick up a bit of wind while cruising the Mediterranean, so check out our excellent sailing yachts now for some true sailing inspiration.

Book your next sailing holiday now!

Photos: onEdition, Emma Pontin, Webb Chiles and NSW Maritime.