How to Give Someone a Surprise Trip This Holiday Season

I love giving presents—I love the challenge of finding something special for someone I love, so that they know I’m paying attention to them & their interests. A great present makes someone feel seen. Sure, I’ll take a look at your Christmas wish list, but I’m also going to try to find something that will be a nice surprise for you!

But I’m struggling this year. My kids have both reached the point where they’ve become increasingly hard to shop for; they’re too old for toys, they like to pick out their own clothes, and they have the significant privilege of already having everything they need. The same goes for my husband, and while I would love to buy something for my him that connects to one of his many hobbies, he tends to be picky about his gear (and he really enjoys doing the research to find the exact right thing). And don’t even get me started on trying to shop for our parents. It’s near impossible.

That’s why for the past couple of years I’ve been trying to give gifts that focus on experiences rather than things. There’s truly no better gift than the gift of experiences—you get the excitement of finding out what it is, the build up of anticipation leading to the actual experience, and it can create memories that last infinitely longer than any sweater or tech item you put under the tree.

The ultimate experience-based gift is, of course, an amazing vacation. Whether it is a two-week African safari for the whole family, or a quick weekend getaway for Mom & Dad, the options are endless. But gifting travel can come with its challenges. It takes planning and consideration. Here are my tried and true tips for gifting travel to family members and close friends.

Keep It Open Ended

If you want to surprise someone with a trip but you’re not entirely sure what they’ll like, keep it open-ended. Perhaps you choose the destination, but you don’t lock down the dates & details yet. Or maybe part of the gift is letting the recipient choose where they want to go. Consider gifting the services of a trusted travel advisor and scheduling a discovery call for the recipient (you can do that HERE).

Don’t forget the little details

There are so many things that go into planning a trip, both big and small. From flights and accommodations, to smaller things like rental cars, lift tickets for the ski resort, park passes for Disney, spa reservations and more. When you’re planning the trip, make sure you don’t forget those small details that bring the trip together.

Make Sure You Know Costs

Are you just gifting flights and accommodations, or are you gifting all of the experiences and details for the whole trip? In either instance, your gift could turn into a financial burden if you don’t know the general costs for all aspects of the trip.

Gift a token that represents the trip

Instead of planning the full trip, gift a token that represents the trip, like a guidebook or a bottle of wine from the destination you chose. Then you can plan the full details of the trip—perhaps over a glass of that wine—with the person you’re gifting. A framed vintage postcard from the destination your loved one will be visiting is another great treat to put under the tree!

Use an incognito browser to do research

The internet has all sorts of ways it tracks information. When you’re researching your trip, do it in an incognito browser tab to avoid target ads being shown to others in your home, tipping them off about the surprise. You can also delegate all of the research and planning to me to avoid discovery at all costs!

Ready to gift that memorable trip? Let’s chat about how I can help you plan the ultimate surprise under the tree! Click HERE to get started!