Why The Thanksgiving Table Is Now a Family Vacation Planning Meeting

My wife, Jillian, and I were blessed to have all three girls home this weekend, and we kicked off the holiday season with our annual November 1^st decorating tradition. Jillian really outdid herself this year. The house looks so festive and I, for one, am looking forward to the holidays this year!

Yes, we know it’s early. But if holiday decorations give us a reason to get all three girls back home for a couple of days, well, bah humbug to you.

Having everyone home at the same time really makes you appreciate how much more valuable that time becomes as your family grows up. As each year passes, getting together takes more and more coordination. Everyone has somewhere to be, something to do, or a schedule that doesn’t quite match everyone else’s.

Which brings me to an opportunity that’s sitting right in front of all of us as travel advisors:

Thanksgiving.

Your golden opportunity

On Thursday, November 26, many advisors' clients will have the people they most want to travel with sitting around the same table. Someone will say, “We should all take a trip together.”

This is a golden opportunity to seed that conversation with some happy travel ideas.

Multi-gen travel is a familiar trend with growing momentum

A survey of more than 3,000 travel advisors worldwide ranks multigenerational family travel as the no. 1 trend for next year. It has climbed one position each year since appearing on this survey in 2024.

Now, if you’re like me, you might reasonably think, “Haven’t we been talking about this trend for years?”

We have. So much so that it almost doesn’t feel like a trend anymore, but just good business. But familiarity doesn’t mean the opportunity has stopped growing. These trips are becoming a bigger part of the business the advisor community serves.

The appeal is easy to understand too. Grandparents want meaningful time with grandchildren. Adult siblings want their children to know one another. Families want to celebrate a milestone while everyone can still participate.

A trip also changes how families spend time together. At home, someone is hosting, cooking, cleaning, or rushing off to the next obligation. When traveling away together, there is room for conversations, experiences, even deepening real relationships, that don’t normally fit at typical holiday get-togethers.

Why this can be good business for you

One family conversation becomes several households traveling, with multiple rooms/ cabins, transfers, excursions, travel insurance, and other commissionable components. That translates to substantially more sales volume from one client relationship.

It can also introduce you to their family members who have never worked with you. Serve them well on the shared trip, and that’s your opening to earn their individual travel business, too.

When you think about it, it’s no wonder multi-gen travel is such a great match for travel advisors. Beyond the attractive economics, these families have a real reason to value your expertise too. Families often bring different budgets, departure cities, mobility needs, and activity preferences. I know if I were the relative who innocently volunteered to “look into it,” calling a travel advisor would be the first thing I did.

Seed the idea

Before Thanksgiving, choose 10 to 15 clients who might welcome a trip with their extended family and send them a personal note during the week of November 16.

Here’s an example, but make it your own:

Hi [Client],

With Thanksgiving coming up, have you thought of going on a trip with your extended family? Even if not, asking ‘Where would we all go if we went on a trip together?’ is always a fun way to get everyone talking and laughing (instead of arguing).

If the conversation gets going and you actually think you’d want to go somewhere together, send me a note, I’d love to help turn the family’s ideas into a couple of realistic options for 2027.

I’m thankful for great clients like you and I hope you and your family have a very Happy Thanksgiving,

[Your name]

Then put a follow-up on your calendar for the week after Thanksgiving and send them another quick note: “Did a family trip make it into the conversation?”

That may feel “pushy” to send that second note, but it isn’t. It will feel helpful if they actually did talk about it. If they didn’t, it just may prompt your client to reach out to some of their family and start the conversation.

Jillian and I were grateful for a couple of days with our girls. Your clients have their own version of that feeling, so give them a small nudge toward more time together. You may help turn this year’s Thanksgiving conversation into next year’s favorite family memory.