Shirley Robertson’s Sunsail family holiday

Shirley Robertson’s Sunsail family vacation

Shirley Robertson OBE recently took her family on their first ever sailing vacation, aboard a Sunsail 444 in Greece.

We spoke to Shirley after she returned from her trip.

So, Shirley, you’ve just got back from your first ever family sailing vacation. How was it?

We were all a bit nervous when we headed out to Lefkas. I was in charge – Captain Mommy! How was it going to work with bossy mom telling the kids what to do on a boat? Would the kids get involved? Would they actually listen to me? Would it be fun?

I need not have worried; they thought it was the ‘best holiday ever’. They loved the adventure of it, a new place to discover every day, meeting other kids, getting involved in boat life. Mom wasn’t seen as bossy, but as knowledgeable.

Where did you go? What route did you take?

Lefkas – Little Vathi – Kalamos – Fiskardo – Sivota – Lefkas were our night stops.  All lovely, but our absolute highlight was Fiskardo; great restaurants and a lovely village. 

Do you have any top tips for islands, anchorages or special restaurants you’d like to share? 

Our favorite lunchtime stop was One House Bay, which has stunning rocks, beaches, and the clearest turquoise water.

The best restaurant we went to was probably Stavros, in Sivota.

Little Vathi had the most helpful marina staff; if you’re at all unsure about parking, they’ll happily hold your hand (well, not literally!)

What was your absolute highlight of the trip? Your most treasured memory?

Apart from the sight of my daughter in a pair of marigolds doing the washing up, I think maybe our last day on the boat.

We stopped at lunchtime, my son steered the boat, and my daughter dropped the anchor. They swam and kayaked for 2 hours before my son put the waypoints in for the way home to Lefkas and sailed the boat home – after 6 days the rhythm of cruising was so natural that I was redundant!

So your children got quite involved in the sailing?

We were a bit short-handed, so the kids had to get involved – there was no option to opt out, and they could see that. As the days rolled on, their confidence grew until they were sailing the boat without me needing to be hands-on. They were happy to do everything: navigating, pulling the ropes, steering.

What did the kids most enjoy?

If I asked them they would say everything, but the reality was the lunchtime stop was a massive hit. We would anchor up in a little bay and they could paddleboard, kayak or jump off the boat… endlessly!

How did you make things as fun as possible for them and keep them engaged, safe and happy?

We planned the day together, where we would go and what we would do, and so I think they felt more ownership of the trip than in a ‘normal’ vacation.

It was full on, there was no time to get bored, and the more they knew about sailing and living on a boat the more fun it was, so they asked a lot of questions.

As for safety – I explained where the risks were; we sailed a lot so I demonstrated the effects of loading on the ropes, and I stressed I was not just Mom on this trip, but also in charge of the yacht.

This holiday must have been rather different to the last time you sailed in Greece when you won your second Gold during the 2004 Athens Olympic Games. As a sailor used to the cutting edge of racing, how easy did you find it to slip into ‘cruising mode’? 

Well, if we came across another Sunsail 444, the race was on!!

I wanted to sail everywhere. I just love it when the engine’s off. Sometimes the kids just wanted to ‘get there’, though.

It was my first time back in Greece since winning Gold in 2004. I’d always wanted to cruise there, but there was never a time before. The islands are stunning, the cruising straightforward and stress-free, the people are so nice, and it’s very, very kid friendly.

What surprised you most about your holiday?

I was stunned how well the kids took to boat life, and how we all worked together; they really wanted to help! We felt like a real ‘team’ by the end of the holiday, which was very special. 

Did you feel you had the right boat? How suitable was the Sunsail 444 for a family vacation in Greece?

The boat was fab, it had everything you could ever want. We loved it!

There were masses of space, heating and AC, 4 cabins, and 4 heads. I’m a huge fan of a catamaran for cruising. I had been slightly worried that it was quite big for us to handle, but it was easy-peasy and the staff at Lefkas briefed us really well and answered all my questions.

Shirley’s children have their say:


I didn’t think I would like it, but by the end of the vacation, I didn’t want to leave! The best bit of the holiday was it felt like we were a million miles away from everything; we didn’t have anything else to worry about apart from the boat. 


I thought that the holiday would be a lot of work, but it wasn’t; it was relaxing and fun. The boat was amazing; it was easy to operate and it wasn’t like a chore because it was fun and active. When we stopped for lunch in some beautiful place, it was like paradise; we would go swimming, paddleboarding, and kayaking. We had so much fun.  

Inspired to follow in Shirley’s footsteps?

Learn more about our bareboat charters from Lefkas.


Ian Pedersen

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