"My wife and I have different ideas about what vacations are all about. Her idea of a good time is to sit on the beach and read. When I go on vacation, I want to do things, and my boys, Jack and Tommy, ages 11 and eight, are the same. I've finally figured out that it's best to hire a local guide. They can handle some of the logistics, and everyone surfs and fishes better when we have someone leading us. Your kids will also listen to a guide more than they'll listen to you, which is key if you want them to learn a new skill, like how to catch a wave. But don't get the guide from the hotel concierge. Make friends with other hotel employees—they usually grew up nearby and have a cousin who surfs or fishes who can show you the real spots. Or use Instagram and reach out to pros who live in the area. You'd be surprised how many of them will respond with good info. I always try to answer people who direct-message me asking for advice."
"My husband and I took our minivan to 23 ski resorts around western North America when our daughter, Betty, was just eight months old. My parents followed in their own car. There were definitely logistical challenges, stressful times, and nights we barely slept, but we were skiing powder and with our family. Minimizing time on the road with the kid was the number-one goal. The roof box on the van was packed. We brought one pair of skis each and not much in the way of clothes—we lived in long underwear. The rest was stuff to keep the baby fed, clothed, warm, sleeping, and amused. We couldn't have done without the $20 plastic sled we bought from a gas station. We used it for entertainment, and it was much smaller and way better on the snow than a stroller. We also found ski towns with great activities for kids. For example, Washington's Mount Baker has cats that live in the lodge, and in Colorado, Crested Butte has a children's museum and there's a petting zoo near Aspen Highlands."
