What 8 Days in Tuscany Taught Me About Group Travel
Before this trip, I had never personally experienced small group touring for myself.
As a travel advisor, I completely understood the hesitation many people have about group travel. Most travelers picture overcrowded buses, rushed schedules, tourist traps, and experiences that feel impersonal or overly structured.
But after spending 8 days exploring Tuscany with Cosmos, a division of Globus, I walked away with a completely different perspective on what modern small group travel can actually look like.
In fact, I’m already looking at planning another small group trip back to Italy… and this time, I want to bring some of you along. So if small group travel has ever even remotely interested you, keep reading.
Farmhouse Dinner - Stay tuned for this story!
This Was Not the Group Travel I Expected
First, let’s clear something up.
This was not 50 to 100 people loading and unloading buses all day.
Our group was just 20 travelers. By the end of the trip, those 20 people felt more like friends than strangers. We exchanged contact information, laughed constantly, shared meals and wine together — and okay, maybe one evening involved a little more Tuscan wine than any of us technically needed, but it also led to one of the funniest nights of the trip and a very appreciated bus ride back to the hotel. We genuinely enjoyed spending time with one another.
Ask me sometime about Bruno, the Bernese Mountain Dog at the farmhouse vineyard where the wine just kept flowing. We tried every version they made while sitting around long tables eating delicious homemade Italian food in the Tuscan countryside. It was one of those evenings where nobody wanted to leave, everyone was laughing, and somehow complete strangers started feeling like longtime friends.
What surprised me most was how naturally the friendships formed.
We had travelers from all walks of life:
Couples
Solo travelers
Families
Friends traveling together
And the ages ranged from 23 to 86.
Our daughter Isabella was the youngest at 23, and Beverly — who quickly became everyone’s adopted grandmother — was 86 years young and absolutely thriving. She kept up with us step for step. I have goals to meet when I get to Beverly’s age. Watching her fully experience Italy with such joy and energy was one of my favorite parts of the trip.
Lisa was a solo-traveler all the way from Australia. She talked about appreciating how our group quickly felt like friends and family, and she didn’t feel alone.
Deni and Laura were long-time friends traveling from Vancouver, but originally were born and grew up in Czechoslovakia. They had the most beautiful accent.
Bob and Mary were traveling with Leslie. Bob and Mary had a son that was marrying Leslie’s daughter in Rome the week after our tour. They decided to come to Italy a little time early and explore before the wedding together. Bob has already shared some wedding photos with our group!
Mike and Sandy were from Michigan and we became fast friends. Isabella is considering Michigan for her graduate school and they were happy to be a contact and place to stay if she visited the campus.
Paul and Sally were siblings traveling together with their significant others and had made it to Europe on a transatlantic cruise! Paul is a big Florida football fan, and is good friends and frat brothers with Steve Spurrier. Being from Mississippi and a true Ole Miss fan, I had to give him a little grief over his Florida football team.
Donna and Trish were nurses from Lancaster County, Pennsylvania. They were so sweet and loved hearing all of Isabella’s plans for grad school as she prepares for the MCAT and on the a MD/phD program.
I could go on and on, my point is we really got to know and enjoy all of our travel companions. There were hugs and maybe a few wistful tears as we said goodbyes at the farewell dinner.
Isabella with Beverly
Tuscany Without the Stress
Our home base for the week was Montecatini Terme, a charming Tuscan spa town that ended up being the perfect location to explore the region without constantly packing and unpacking.
From there, we explored:
Lucca
Pisa
Greve, home of Chianti Classico
Vinci
Bolgheri
Castagneto Carducci
And yes, we absolutely tasted our way across Tuscany.
Wine tastings. Olive oils. Long lunches. Tiny hidden restaurants. Family-owned wineries. Gorgeous countryside roads lined with vineyards and cypress trees.
The kind of places you probably wouldn’t stumble upon on your own.
La Regola nestled in the hills of Pisa on the Riparbella area - this was a gorgeous vineyard and wine tasting experience
The Biggest Surprise? How Relaxing It Was
As someone who plans travel professionally, I’m very used to handling logistics.
But there was something incredibly freeing about not having to think about:
Driving narrow Tuscan roads
Parking
Train schedules
Navigation
Timing tickets
Coordinating reservations
Figuring out where locals actually eat
It was all handled.
We simply showed up and enjoyed the experience.
Instead of staring at Google Maps or worrying whether we were late for the next reservation, we were sitting in Tuscan piazzas enjoying wine, talking with new friends, and actually soaking in the experience.
We visited a bakery in Montecatini where we got to go into the kitchen and make foccacia and taste all the treats!
Local Expertise Makes a Huge Difference
Our tour director, Gian Paulo — though he quickly told us to just call him JP — was fantastic. He is from Sorrento in Southern Italy.
He kept us organized, on time, informed, and entertained without ever feeling overbearing. By the second day, we all knew his favorite phrase: “Andiamo!” It didn’t take long for everyone to figure out that meant “Let’s go!” in Italian, usually followed by all 20 of us hustling back onto the bus laughing.
You could tell he genuinely loved Tuscany and wanted us to experience it beyond the typical tourist version.
That’s another thing I didn’t fully understand until this trip:
good group travel gives you access to local expertise you simply can’t replicate by Googling your way through a destination.
We had expert local guides in different towns, insider stories, hidden gems, and experiences that felt authentic rather than overly commercialized.
Some of our favorite moments were places we never would have found on our own.
During one stretch of free time, about 10 of our 20 travelers decided we were simply too close to Pisa not to go see it for ourselves. So we hopped on a train from Montecatini and made a little side adventure out of it.
And yes… this also happened to be the day one of our friends had a little run-in with a pickpocket on the train ride to Pisa. Thankfully, they handled it incredibly well and didn’t let it ruin the trip at all. If you haven’t read my blog about that experience and some important European travel safety tips, definitely go check that one out too.
After visiting the cathedral and finally seeing the Leaning Tower of Pisa in person, we grabbed pizza and beer before heading back to Montecatini. It ended up being one of those spontaneous travel days that you remember just as much as the planned excursions.
Our side trip to Pisa
The Social Aspect Was Unexpectedly One of the Best Parts
One thing I did not expect was how much I would enjoy the people.
By day two or three, our group naturally started gravitating toward each other at breakfast, on the bus, during wine tastings, and over dinners.
We celebrated birthdays together, swapped travel stories, laughed at inside jokes, and by the end of the week, none of us really wanted to say goodbye.
There’s something special about traveling with people who all share the same curiosity and excitement about experiencing a destination.
And for solo travelers especially, I can now fully see the appeal. You have built-in companionship without ever feeling forced into constant group interaction.
Our farewell dinner at our hotel - JP, our tour director is standing at end of table.
Why I Think More People Should Consider Small Group Travel
I still love customized independent travel. I always will.
But I now think small group touring fills a space that many travelers overlook.
It’s ideal for travelers who:
Want to experience Europe without handling every detail themselves
Feel intimidated by driving internationally
Want deeper cultural experiences
Like the idea of built-in social connection
Want expert guidance without sacrificing authenticity
Prefer smaller, more personal experiences over giant tour buses
And maybe most importantly:
you don’t feel alone while traveling.
There’s something really special about sitting around a table in Tuscany with people who, just days earlier, were complete strangers.
This experience is saved for another blog! Full story to come!
Would I Do It Again?
Absolutely.
Thank you JP, Tuscany and Cosmos tours for giving us memories that will last a lifetime.
I think this experience completely changed how I view group travel.
Modern small group tours are not the old stereotypes many people still picture.
Done right, they feel immersive, personal, social, and surprisingly stress-free.
And sometimes, the people you meet along the way become just as meaningful as the destination itself.
If a Tuscany-style small group tour has ever crossed your mind, this is me telling you: give it a shot. You may end up loving it as much as we did.
And if you’re curious whether a small group tour might fit your travel style, I’d love to help you find the right one.
This is Mike and Sandy from Michigan -we were fast friends. University of Michigan is on Isabella’s list of grad schools she’s applying to and Mike and Sandy live outside of Ann Arbor and were happy to be contacts if Isabella goes to Michigan. We plan on staying in touch!
Melissa@wandersbymelissa.com | WANDERSBYMELISSA.COM | 601-540-7336
