Three Things I Always Tell Friends Before They Book a Family Trip

December 14, 2025

(And why they matter more than you might think!)

Planning a family vacation can feel exciting, overwhelming, and chaotic—all at the same time. Between school schedules, kids’ activities, budget considerations, and figuring out what destination works for everyone, it’s no surprise that many families feel stressed before the trip even begins. As someone who walks families through this every day, I’ve learned that a few simple guidelines can make the entire experience smoother, more enjoyable, and way more memorable.

One of the biggest factors people overlook is timing. When you travel can completely change your experience, especially for families. Crowd levels, pricing, weather patterns, and even the overall energy of a destination shift with the calendar. A trip during peak spring break feels totally different from the exact same itinerary a couple of weeks earlier or later. Sometimes shifting your dates by just a few days can mean shorter lines, better resort availability, and more relaxed kids (and parents!). Timing truly sets the tone for the whole vacation.

The second thing I always remind people of is this: the cheapest option is rarely the best option, especially when traveling with kids. A great deal isn’t always great once you factor in convenience, comfort, and logistics. Maybe that discounted flight requires two layovers. Maybe the “bargain” room is a tight squeeze for a family of four. Or perhaps the resort that looks perfect online is actually massive, meaning long walks back and forth for naps or breaks. When it comes to family travel, value beats price every time.

Next comes the topic everyone loves to ignore until it’s too late: travel protection. Kids get sick. Weather changes. Airlines delay flights. Life happens—and when you’re investing in a family trip, the last thing you want is to lose the money or the memories. Travel insurance gives you peace of mind and flexibility when plans inevitably shift. It’s one of the smartest choices a family can make, and one I never skip myself.

When families keep these three things in mind—timing, value over price, and travel protection—the entire planning process becomes easier. Decisions feel more intentional, stress decreases, and the focus shifts back to what truly matters: enjoying the experience together. Planning a family trip shouldn’t feel like a chore. With the right guidance, it becomes something to look forward to.At the end of the day, travel is about connection. It’s about shared moments, new experiences, and the kind of stories your family will talk about for years. Whether you’re dreaming of the beach, the mountains, a theme park, or a cruise, taking a little extra care in the planning phase makes all the difference.