Celebrating the Preppy Lifestyle and it's sensibilities


As you may already know, I'm passionate about sailing. So I tend from time to time to check out the regatta scene in various areas, check out sailing websites and even view sailing DVDs. Which leads me to the latter. I got a DVD about a year ago called 'Sailing with Penny Whiting'. I hadn't really viewed it until recently. Man was I impressed. This woman has got her s_ _ t together. Sailing can be a rewarding but honestly, there are tasks that have to be mastered. It can dishearten a beginner. Yet Penny has such a way of teaching, that you come away feeling as though anyone can and should sail. That's precisely Penny's mission.  I was so inspired that I had to contact the first women to race in the Congressional Cup, Long Beach California in 1971 to get her take on sailing for beginners. Running her school in New Zealand, she was so gracious enough to grant me an interview. 

The Preppy Times:  Right, so tell me Penny how did you get started Sailing?

Penny Whiting:  My family sailed and I was on a boat the day I was born.

TPT:  Tell me why should anyone sail?

PW:  Sailing is just one of life's great pleasures.

TPT:  Do I understand right that you've designed yachts?  How did you get started with that?

PW:  My brother Paul designed and built our boats.  I was just the sailor.

TPT:  Right then, what's the greatest challenge you've faced sailing?

PW:  Finding land when you do not want to get to shore.

TPT:  When did you start the Penny Whiting School?

PW:  I was seventeen in 1967 I guess.  43 years of teaching interesting people the joys of sailing
with safety and confidence.

TPT:  What does your courses include?

PW:  I run a complete learn to sail course for beginners, as it is all practical we really get some great  sailing in Auckland.

TPT:  What would you tell a person who's thinking of pursuing sailing?

PW:  Have a go and see if you like it.  With no theory and all practical is always fun.

TPT:  What advice would you give a neophyte with doesn't own a yacht but is interested in sailing?

PW:  Hey if you have learned to sail you are good crew for anyone as you have learned to be told
and understand the terminology and boat handling.

TPT:  What's the regatta scene like in New Zealand?

PW:  Most clubs race at least twice a week so you can sail every night after work.

TPT:  How is racing different than sailing?

PW:  Hey hold off on the racing unless it is the only sailing you can get and they get really picky and stressed racing their best mates.

TPT:  My wife always complains that for something that is supposed to be relaxing, there is too much work to do with regards to running a yacht. What do you say to something like that?

PW:  Sailing is about timing not strength or stress, anybody can sail if they get the timing correct.
Women are natural sailors as they multi task.

TPT:  Your yacht 'Endless Summer' is a magnificent specimen, really beautiful.  Would you tell a
little about her?
PW:  Endless Summer sums her up, a real gem to anybody to sail and I sail her often for pleasure
by my self.
TPT:  What's been your favorite yacht to sail?
PW:  Endless Summer!
TPT:  What's the best boat in your opinion for a beginner?
PW:  Any boat is just great, the bigger the better and easier to sail.
TPT:  How long would you say does it take to master the basics of yachting?
PW:  I feel I can give a person a really good understanding in 15 hours practical.
TPT:  Throughout your years as a yachtswoman, where did you find the sweetest waters for sailing?
PW:  Auckland Harbour.
TPT:  Do you have children?  If so, are they following in your footsteps?
PW:  I have a daughter living in Hong Kong that is a good sailor.  And my son has done 4      Americas Cups and sailed in the Olympics as a sailor.

TPT:  If you weren't running the Penny Whiting School, what else would you be doing?

PW:  I just love messing around in boats.
TPT:  What else would you like to share with the novice sailor?
PW:  Just do it if you want to, you have one life and it is short.  Do what you want to do.
TPT:  O.K.  last question, wood or fiberglass?
PW:  Fiberglass for easy maintenance and re-sale, more sailing, less work if you keep it polished.
TPT:  Thank you Penny, it's been a pleasure.
PW:  Phew great questions, well done.
Penny Whiting can be reached at  but book early as her school is located in Auckland, New Zealand.  That would make a wonderful vacation, wink, wink.

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