Luxury Family Holidays Handpicked for Parents

Kodomo Q&A

Lucy Kaylin, Editor-in-Chief of O, the Oprah Magazine.

Lucy Kaylin, Editor of O, The Oprah MagazineLucy Kaylin has the incredible position as Editor-in-Chief of O, The Oprah Winfrey Magazine. After working at Vogue, GQ and Marie Claire, she assumed the position of deputy editor at O before moving in to the top spot of editor-in-chief last year. Despite what must be an unimaginably busy work schedule, she has published The Perfect Stranger, a book that analyses the very complex relationship between working mothers and their caregivers. The writer, editor and mother chats to us about holidays with her children and early travel memories.

Q: What is your first childhood memory of travel?

I think it was when I went to Mexico with my family. A very vivid memory for me was my parents endless and fruitless search for something resembling pizza or a hamburger for me to eat. That really dominates the trip as far as my memory can recollect. Finding food I would deign to eat was toughest in the Yucatan; I remember it being spectacular, but I also remember being grumpy and hungry.

Q: Where have you had your best holiday to date?

The trip we just came back from was probably the best one. It was to Deia in Mallorca. It was really fabulous. My children are teenagers now and that much more able to appreciate it and wander into town by themselves, which was a lot of fun. They would come to the local watering hole, Sa Fonda, with us and dance. It was really a fabulous trip. We rented a house with another family and we were very close to town; it was a fun place to be with the family.

Q: Where was the first place you went with a little one in tow? How did it go?

It was to Block Island, which is a little island off Rhode Island. It was the perfect place for where we were at, at the time. It’s incredibly casual and forgiving. We have pictures of our 1-year old Sophie walking down the street in her diaper. I remember there being farm animals to entertain her and it’s a place where you can fly kites, go the beach and just sack out. It was perfect for harassed and harried parents of a new baby.

Q: How do you find the experience of travelling with children generally? A wonderful, bonding experience, for example, or traumatic and stressful?

I think a mix of all those things. We have certainly created incredible memories on all the trips we’ve gone on. My children have seen amazing things and amazing parts of the world, but I would say I always found it stressful, because I worried if they were having a good time and worried that we weren’t doing enough or seeing enough. I can get a little anxious about that if we’re not seeing the sites and making the most of every moment.

Q. Do you ever travel with your children for work?

I really don’t. I do lots of fun, work-related things with them here in New York. For instance, I take my daughter to shows during fashion week, but I really haven’t taken them on work trips. That sounds to me like it could be wildly stressful, so best to leave those two spheres separate.

Q: Where has been the best holiday with your children?

It’s going to sound uncool and unhip, but several years ago we went on a Disney sponsored trip to Paris and London and, say what you will, it was fantastic on every level, particularly for where my kids were at, age-wise, at the time. In the Disney way they thought of everything and the whole experience was full of treats and surprises. I remember we went to see The Lion King and we were on a tour so we were told to stay in our seats at the end to let everyone get out the theatre before we went back to our bus. In fact, we were getting a back stage tour instead so the kids saw all the costumes. When you have kids that age, it’s the best thing for them. I’ve always been very grateful for that trip.

Q: And your worst?

I don’t think there were ever any disasters. Even back when we couldn’t stay in the nicest places there is always something magical about being away with your kids and having them all to yourselves. I would be nitpicking if I said one was less good than another. They have all been good in their own way.

Q: What is your must-have travel accessory when away with children?

Then, as now, board games. That’s critical and it’s always been a ton of fun for us. It’s a great way to unwind at the end of a busy day of travel or sightseeing. That’s been a special thing for us and it’s a great way to bring the temperature down.

Q: Do you have any personal top tips for travel with kids?

I think the biggest thing would be remaining cool as a mum with downtime. This goes to what I was saying earlier about being stressed and agitated about whether we’re making the most of the trip. I think it’s so important to learn that there’s loads of pleasure and peace to be had in just letting them crash, because they need it. They really, really need to just daydream and sleep and, yes, check in with their devices, and not feel that parental pressure to do, do, do and see, see, see. If parents can learn to build that into a trip I think that’s incredibly important and will save them a lot of grief.

Q. What made you decide on Europe this summer?

One wants to go to Europe so it’s not a hard choice to make. I think a big part of the choice this year is the fact that my daughter is in her last year of high school and she’s looking around at colleges. We all had a really bittersweet sense of this being the last trip of this type during this chapter of the life of our family. I hope, and believe, we’re going to be travelling together in the future in new configurations, but in terms of her living under our roof and being there with us as we plan the trip and make these family decisions together, it did feel like this was the last of those. She very much wanted to go to Mallorca when our friends suggested it and that seemed like a great idea.

Q. Do you have a personal favourite must-have travel accessory for yourself when travelling either short or long haul?

A sketchbook and good pencils and, if you can bear it, some watercolors. And flip flops. Even if it’s cold out there’s something about flip flops that suddenly puts you in vacation mode.