How to Get Your Family to Say YES to a Big Trip

Tips for Turning “Maybe Next Year” into “Where Do I Pay My Deposit?”

I've been getting a lot of requests recently for assistance with family trips and to know me is to know that this is my wheelhouse and where I got my start! So let's talk about it.

Let’s be real: sometimes the hardest part of planning a family vacation isn’t picking the destination—it’s getting everybody to agree to go. You know the ones: Your cousin who needs six reminders on what dates.

Your sibling who swears they’re in... until it’s time to pay. The auntie who’s worried it’ll be too much walking, too many people, or too far from home.

It’s a whole process, but it’s not impossible. If you’ve got the vision, I’ve got some tips to help you bring the crew together and make that trip happen.

1. Lead with the why

Don’t just pitch the “what.” Pitch the reason.

Is this a chance to reconnect after too much time apart? To celebrate a milestone? To explore heritage or culture together? People say yes when they feel emotionally invested, and you get to be the one to paint that picture. One of the biggest trips I've been on was my parents' 30th anniversary and vow renewal. Some close runners up include my grandma's 75th and 80th birthdays. A cause can really get those teetering family members off the fence.

2. Pick a trip that fits the group (not just the dream)

Yes, that overwater bungalow in Bora Bora looks great, but maybe your crew needs something all-inclusive, easy to get to, or payment-plan friendly. Cruises, resorts, and cultural tours are great options with built-in flexibility and minimal stress. The right trip for the group makes all the difference.

3. Give them a clear budget + timeline

People don’t like to be surprised by money. Break it down early:• Total cost• Deposit amount• What’s included• When final payments are due and if you're working with a travel advisor (hi, it’s me 👋🏾), I’ll make sure the payment plans are simple and the updates keep flowing.

4. Find your “yes” people first

You don’t need everybody to say yes right away. Start with the ones who are already on board or almost there. A little momentum goes a long way and once folks see others are in, that group chat energy changes real fast.

5. Be flexible... but not forever

You want this to be fun, not stressful. If your people need a minute to think, let them. But don’t let the whole trip stall out waiting for one or two indecisive people. Set a soft deadline, make decisions, and let others catch up if they’re serious.

6. Remind them: life is short, memories matter

Sometimes people need a sentimental nudge. Remind your family that these moments don’t come around often and you’d rather be laughing over dinner on a beach than wishing y’all had gone when you had the chance.

Thinking about a family trip?Let’s start planning now—whether it’s Ghana, a holiday cruise, or a dreamy resort for Fall Break. I’ll help you sort out the details, pitch it to your people, and make it as stress-free as possible.

Shoot me a message and let’s get your “yes” crew together.

Whether you need help choosing the perfect destination, putting together the details, or just getting your people to commit, I’ve got you.

📧 Email me at: info@reidtravelteam.com📞 Call or text: 678-749-6592 -- let’s book a quick planning session!

Let’s turn “maybe next year” into “this is really happening.” ✈️