Planning a group trip can feel a little like organizing Thanksgiving dinner… if the turkey needed a passport and your cousin changed her mind about coming every other day.
But when it works? It’s magic. ✨
There’s nothing quite like watching everyone you love unwind together in a place where the hardest decision is beach or pool, nap or cocktail.
And here’s a little insider secret: fall is one of the best times to start planning a group getaway.
Why? Because while everyone else is thinking about candy corn and Christmas shopping, the smartest travelers are quietly locking in next year’s warm-weather escapes.
Here’s why this season hits the sweet spot:
🍁 Better rates and availability in the fall — The post-summer calm means fewer crowds and more options before prices climb for the holidays.
📅 Easier scheduling — With school routines settled and no major holidays in the way, it’s easier to coordinate calendars. It’s way better to plan over a year in advance so everyone can block their calendar to be there together.
💬 More meaningful connection — There’s something about crisp fall air that reminds us to slow down, reconnect, and make memories — whether that’s around a resort dinner table or watching the sunset at sea.
Some of my favorite group trips lately have been all about connection over perfection:
✨ A mothers & daughters trip to a Riviera Maya resort where matching swimsuits somehow made it into every photo.
🎉 A high school graduation cruise for a group of families — what an amazing way to celebrate such a momentous occasion!
🌴 A “just because” friends’ getaway to Jamaica for a few couples together — no occasion, no stress, just good vibes.
The secret to pulling it off (and actually enjoying it)? Let someone else handle the chaos behind the scenes.
That’s where I come in. I help you pick the perfect spot, manage the payments, and keep everyone on the same page — so all you have to do is show up and make memories.
So, if you’ve got a group in mind — big or small — now’s the time to start dreaming.
You bring the people.
I’ll wrangle the group chat.