Picture this: your family gathered around the dinner table, the smell of delicious food filling the air, and laughter echoing from the playing kids through the house. Someone brings up a favorite memory from a past vacation, like that time on the maybe that beach trip where everyone stayed up late for s’mores, or the time you got lost in a new city and ended up discovering a hidden gem of a restaurant.
Before you know it, the room is buzzing with shared memories and jokes from past family trips and experiences, and it feels great. That’s the magic of the holidays. So why not keep that feeling going? When everyone’s together, relaxed, and in the mood to dream a little, ask everyone if they’d like to take another family trip.
Start the conversation when everyone is together
Holiday gatherings are the perfect place to spark travel ideas. But you don’t have to make it a big announcement. Instead, slip in a question or two between meals, games, or dessert. It’s a great way to see everyone’s eyes light up and start imagining what kind of trip you could take together. Here’s why it works so well:
- Instant feedback: Everyone’s already together, so you can talk through ideas right away.
- Shared excitement: The energy in the room builds as people start dreaming together.
- Coordinated scheduling: Everyone can pull out their calendar and check for potential dates.
- Fresh ideas: Someone might suggest a destination you’ve never thought of.
Keep the conversation fun
The easiest way to derail a trip-planning session, especially with a large group, is to get too serious too quickly. So instead, keep it lighthearted. Instead of asking, “Where should we go?” (which can feel overwhelming), guide the discussion with simple questions that spark imagination and make it enjoyable for everyone.
Family trip conversation starters
Here are a few ways to kick things off naturally:
- “What’s one place everyone has always wanted to visit together?”
- “If we could take a trip anywhere, no limits, where would it be?”
- “Would you rather relax on a beach, explore a new city, or go on an adventure?”
- “What’s one activity you’d love to do as a family—something we’ve never done before?”
- “When would be the best time for everyone to travel next year?”
You can even make it a game. Write ideas on slips of paper and toss them into a bowl. Then take turns pulling them out and sharing what sounds most exciting.
Why family trips are worth it
When the conversation starts, remember you’re not just talking about a vacation. You’re creating the foundation for new memories that your family will cherish for years to come. So if the naysayers start reminding them of the joy you feel when you’re together and how travel enriches your lives. You could even mention a few of these benefits, like how:
- You’ll build stories that will be retold at future holidays.
- You’ll grow closer through shared experiences and laughter.
- You’ll get quality time together, with space for everyone to relax and recharge.
Planning a group trip doesn’t have to be stressful
As you make your holiday list and check it twice, add one more thing: plan your next family trip. The joy, laughter, and connection you share during the holidays don’t have to end when everyone heads home. One simple conversation could turn into your family’s next great adventure.
At Creating Magic Vacations, we handle all the planning details, from booking your accommodations to arranging excursions, so you don’t have to stress about coordinating a big group trip. All you need to do is decide where you want to go and when, and we’ll take care of the rest. So go ahead and start that conversation. Your next unforgettable family adventure is waiting.



