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Inspirational Women Travellers: Captain Holly Scott


Meet Captain Holly Scott. With her daughter Katie, also a licensed Captain, Holly runs Mahalo Sailing, which specialises in group sailing adventures and private charters around the world. from Tahiti to Ireland to Mexico

That’s exciting enough, but what really grabbed our attention is that all of Mahalo Sailing’s crews are female, and Holly or Katie captain every trip they organise. The female presence is important to Holly, who believes that having an all-female crew encourages a more supportive atmosphere, leading to strong bonds and life-long friendships among the all-female sailing groups.

Holly’s relatives crossed the Plains in covered wagons to reach California, where she still lives. Holly started travelling as a child and first went sailing as an infant. “I remember steering our small sailboat at the age of 3. Santa Claus gave me my first boat at 9 and I have owned a boat since then. About 25 years ago I decided to make my passion my profession and studied for a US Coast Guard Captain’s License.”

“Now in her mid-60s (“I still can’t believe I’m a day past 30. Dammed mirrors… “), Holly has got around 200,000 miles “under my keel”.”

Her sailing career has taken her to the West Coast of North and Central America, much of the South Pacific, between Hawaii and California, the Caribbean, and parts of Europe.

Read on to find out more about Holly’s remarkable life in sailing – and how you can join her in Croatia and Ireland for a taste of life at sea too!


What lures you to the ocean again and again?

It’s hard to put into thoughts and words.  It’s such a ‘feeling’…  I love the grounding feeling of the water.  While it’s always moving it’s also very settling because on a grand scale, it’s also constant.  I love the constant changes, if that makes sense.  The sea can be moody - mellow, angry, playful, loving and powerful.  Living my life on the water has taught me to leave her be when she’s upset.  It will pass.  She’s always back to her lovely self at some point and then we play together again.  She’s a powerful teacher, and every time I’m on the water I learn something new.  I’m never bored.

“Living my life on the water has taught me to leave her be when she’s upset. It will pass. She’s always back to her lovely self at some point and then we play together again.”

What's your favourite trip?

Wow!  So hard to decide on a favorite.  I love so many parts of so many trips.  The vastness of the sea when you are a tiny speck sailing along, sharing crazy experiences with good friends and laughing your way up the West Coast of the US, the amazing friendships that develop on our charters, that mother/daughter cruise when she is old enough to take over, sharing Tahiti with friends….  It’s all my favorite! 


Tell us about your scariest encounter on the water?

I taught sailing for a million years and began to specialize in teaching (or maybe coaching is a better word) women who had sailed and had some scary experience.  I learned that they were scared because they didn’t know what to do, and whoever was in charge didn’t either and was yelling and shouting.  Then I started trying to remember being scared.  I could remember being scared as a child when it was very windy and I didn’t know what to do and I didn’t want to end up in the water.  I threw myself into learning as much as possible and reading about other people who had had challenging experiences and how they dealt with them.  I realized that I wasn't afraid.  I have a powerful respect for what can happen ‘out there’ and go to great lengths to avoid that kind of excitement, but if something unexpected comes up, as it can, I know how I’m going to deal with it. 

Holly did go into some detail about her scariest encounter – and it long but too edge-of-your-seat fascinating to leave out! You can read it here.


And your most wonderful sailing experience?

My most wonderful experiences always involve sea life.  We were moving a friend’s boat from Los Angeles to Seattle, about 1,750 miles.  The first hurdle is Point Conception, which has a reputation for a nasty passage around it.  I was really watching the weather and saw the perfect conditions for the next morning.  We approached the point but were not in any rush because we were going to anchor for the night and round it at dawn.  We saw some dolphins on the horizon so headed in that direction.  Then we saw more. And more!  Super pods!!!  There were thousands of them all swimming together making so much noise!  We were motoring and shut off the engine to listen to them.  Breathing, splashing, squeaking… So amazing!!!  Then a whale came up!  And Sea Lions! Everywhere we looked, there were animals!  Even some giant Mola Molas!  We 4 friends were squealing with delight.  This went on all afternoon and we were exhausted by the time we anchored for the night.  4 years later, we still talk about it when we get together.

“We were motoring and shut off the engine to listen to them. Breathing, splashing, squeaking… So amazing!!! Then a whale came up! And Sea Lions! Everywhere we looked, there were animals! Even some giant Mola Molas!”

Have you encountered any difficulties in the sailing world because of your gender?

Oh sigh….  yes, gender issues are endless.  There are so many instances of gender bias, I can barely remember the details.  Like most things, we have to be so much better at what we do to even be considered equal, and even then it rarely happens.  It’s exhausting.  I found having grey hair helped for a bit, maybe more experienced or something, but it’s never enough.  At some point you go from being thought of as ‘Just a woman’ to be thought of as ‘Just an old woman’.  Ugh. 

Every year, I put together a huge week-long event for a women’s sailing Facebook group.  One year we were in Belize and donated a bunch of money and supplies to the local animal shelter.  A spokesman came to our dinner to accept the donations and to thank us.  He clearly had no clue what our group was about.  We presented the shelter with a mountain of animal supplies, a huge envelope of cash and took the required photos for the local newspaper.  The spokesman looked around at us and exclaimed “Wow!  You're just a bunch of women!”  There was a stunned silence from our group of 60 women. And then somebody broke the ice.  That became our mantra for the week.  Yep, Just a bunch of women, sailing without men for a week in Belize.  Yep.

“My favorite part of these trips is watching the bonds that form and become life-long friendships. We have an amazing tribe of women who support each other, long after the trip has ended.”

What's it like to manage a female group tour?

At the beginning, before we head off to our destinations, managing the group is a bit like herding cats.  Once we get a trip filled, we start group chats so everybody can get to know each other ahead of time.  People come from all over, so it’s good to have an idea about everyone.  I think my favorite part of these trips is watching the bonds that form and become life-long friendships.  We have an amazing tribe of women who support each other, long after the trip has ended.  They often maintain their chat groups and visit each other, plan more trips, suggest new ones for all of us to do, invite their friends and we all have a grand time.  There have been a few square pegs over the years but the tribe is wonderful and supportive of everyone.  We are of all ages, all shapes and sizes, lifestyles, professions, married, single, widowed, divorced, gay and straight and trans, you name it.  I am proud of the group we have become.


The Croatia trip you’re planning has female Captains and First Mates. How does having female captains and first mates affect the trip?

All my Captains and First Mates are Female.  They are all very accomplished, very professional and a lot of fun.  You can know how to drive a boat and still be a lousy captain if you don’t like people, so I choose them carefully.  It’s so much easier to have female crew.  I have found that women learn more from women and are more relaxed.  We bond with our sisters more deeply when the guys stay home.  We eat the way we like to eat, discuss our own topics, share everything more, hug more and maybe shed a tear or two, all in a super supportive atmosphere.  And, we’re just more fun!  On some trips, we have male and female guest boats but I always have Women Only boats and all boats have female crew.


Do you need any experience to go on a sailing trip?

All my trips are No Experience Necessary.  I have some who just want to relax and watch the world go by, and some are all about learning and perfecting sailing skills.  My trips are not sailing classes, but I put it on the guest to discuss their goals with their crew.  There are many who want to fine-tune some skills in particular so the crew will always work with that person whenever possible, without impacting the vibe of the entire boat.  No written exams! Ha ha!


What would you say to any women reading this and wondering if a sailing trip is right for them?

If you like to be in the company of wonderful fun women, love being outdoors, love to laugh, explore, experience new things, love great food, are fit enough that you can get up off the floor from a sitting position and want to make the most of every day, you’re perfect for these trips.


Captain Holly is currently planning sailing trips along the River Shannon in Ireland and to Croatia’s islands. You’re invited to join her!