It starts in the group chat.
Someone says, "We should go to Italy together!"
Everyone's excited. Hearts and fire emojis.❤️🔥 "Yes!" "Finally!" "Let's do it!"
Then... silence.
Because someone has to actually plan it.
Someone has to research the regions.
Compare the hotels.
Figure out if six people can fit in one car or if you need two.
Find restaurants that take reservations for groups.
Coordinate everyone's opinions—and everyone has opinions.
That someone?
It's always one person.
Usually the same person.
Usually the one who's "good at this stuff."
I know because I've been that person.
Long before my travel advising days, I was the default planner for my extended family.
Every trip. Every detail. Every "what's the plan?" text.
I'll be honest—I had a meltdown or two.
It's overwhelming.
And it takes the joy out of the trip before it even begins.
You don't get to enjoy the anticipation.
You're too busy managing logistics, fielding questions, and second-guessing your choices.
By the time you arrive, you're already exhausted.
That's not a vacation. That's a project.
What if no one had to wear that hat?
I've been curating more group trips lately, and I want to tell you what they can look like.
For a group of three couples in Tuscany:
A restored farmhouse with a pool, surrounded by olive groves. Everyone under one roof, but with space to breathe.
A private chef comes three nights a week—she sets up in your kitchen, you watch, you sip, you eat at a long table with the people you came with. No reservations. No rushing.
A truffle hunt one morning, followed by lunch made from what you found.
A family wine estate that doesn't take tourists—but takes you, because I know them.
And plenty of unscheduled time. Read by the pool. Wander the village. Nap without guilt.
For a multi-generational family:
An agriturismo, villa, or apartment rental where everyone can be together under one roof—but with enough space that everyone has room to breathe.
Activities designed for different energy levels.
The grandparents take a slower morning, rest in the afternoon, join for aperitivo.
The twenty-somethings hike or bike to explore a nearby town.
The parents do a cooking class, a wine tasting, a leisurely wander.
Everyone comes together for dinner.
That's the magic—the shared meal at the end of the day, swapping stories about what you discovered.
I did this recently for a family of seven. Three generations.
The oldest was in his mid-70s with some mobility considerations. The youngest was in high school.
Here's what they told me:
"Italy has been absolutely wonderful! The tour guides were fabulous—they were so considerate of my Dad when he needed to go slower! We have loved the food, the people, and the history of Italy! Thank you so much for all the details that I know you put into place for our family—they haven't gone unnoticed!"
That's what's possible when the trip is designed around YOUR group—not a template.
Here's what it comes down to.
You don't have to choose between a cookie-cutter group tour and the chaos of planning it yourself.
There's a middle option.
I curate the whole thing.
I coordinate with my Italy partners.
I handle the villas, the hotels, the private chefs, the experiences, the logistics.
Everyone in your group gets the itinerary.
Everyone knows the plan.
And the person who usually plans everything? They finally get to be on vacation too.
If you've been dreaming about a group trip to Italy—whether that's couples, friends, or multiple generations of family—I'd love to talk about what's possible.
Let's plan your trip.
A presto,
P.S. — If a group trip has been floating around in your mind, hit reply and tell me what you're envisioning.