When our good friends Curt and Joy Grady headed to Italy for a whirlwind trip a couple of weeks ago, they had a very important travel companion in tow: our trusty 12-bottle Flies With Wine Wine Suitcase.
Curt was kind enough to play field tester and keep us updated with live texts and photos along the way. From navigating international airports right on the heels of the Winter Olympics in Milan to high-speed rail, cobblestone streets and Tuscan wine country, the suitcase got a serious workout!
As they journeyed from the storied streets of Florence into the rolling countryside, the landscape shifted dramatically into iconic vistas of stone towers, medieval charm, and sweeping vineyards.
Here is the play-by-play of how our favorite piece of wine gear handled the ultimate Italian road (and rail) trip.
Phase 1: Touchdown in Milan – February 26–27, 2026
The adventure kicked off before they even left the ground, with Curt promising regular dispatches from the road:
He said, “The adventure begins! I will keep you updated on the travels of the wine suite case!”
After a smooth flight, the suitcase made its official international debut at the Milan International Airport, posing against a backdrop celebrating the recent 2026 Winter Olympics. It didn’t take long for the heavy lifting to begin.
“We are tracking the journey of the wine suitcase. 1st stop Milan International Airport and of course a 2026 Winter Olympics background. The hard work may begin for the suitcase tomorrow….with our 1st wine tasting. More to come…” he reported and then went on to say, “Light day today for the Wine suitcase. 1st two bottles.” (See right)
Curt and Joy settled in to allow the jet lag to subside as they found their footing, doing, you know, touristy things. Taking pictures. Drinking wine. Drinking a little more wine… And the great thing about Milan is its history!
They even had the magnificent Duomo di Milano Cathedral towering in the background of their photo, creating a unique photo bomb situation! It’s one of Milan’s most iconic landmarks and a fantastic spot for a travel selfie!
Oh, have we officially introduced Curt and Joy yet? Allow us to do just that! Meet our friends, Curt and Joy!
Phase 2: Trains, Cobblestones and Tuscany – February 28, 2026
Next UP was a train ride DOWN to Florence, followed by a transition into the heart of Tuscany and a scenic stop in San Gimignano. Tuscany’s history is steeped in ancient roots, dating back to the Etruscans who first planted vines across the hills long before the region flourished during the Renaissance. That rich agricultural heritage is still visible today, where centuries-old stone farmhouses, medieval towers, and historic hill towns stand as timeless testaments to a landscape shaped by generations of tradition.
Visually, the region is legendary for its idyllic, postcard-perfect scenery of undulating hills, cypress-lined driveways, and sun-drenched vineyards. Manicured olive groves and golden wheat fields sit side-by-side with rugged terrain, creating a harmonious landscape that shifts dramatically in color and light across the seasons. It is a terrain designed for slow exploration, where every turn reveals a sweeping vista of rustic beauty that has inspired artists and travelers for generations.
“Tuscany is a hideous place…” 🤣 Curt
Have we mentioned that Curt has a sense of humor much like Phil does? Some might even say warped. Perhaps even demented. His description of Tuscany, found in the caption of the above photo, says it all. And this would also be a good time to mention that Phil added a little graffiti to the featured image of this blog post. We want to make this perfectly clear, the Grady’s did NOT deface this marvelous Italian sign or any OTHER person, place or thing in Italy!
Winemaking in this storied region is equally iconic, defined by a magnificent balance of tradition and world-class craftsmanship. Tuscany is globally celebrated as the birthplace of Sangiovese, the premier grape behind legendary appellations like Chianti Classico and Brunello di Montalcino, known for their vibrant cherry fruit, structure and earthy complexity. Alongside these classic powerhouses, the coastal areas and valleys give rise to prestigious Super Tuscans—innovative blends featuring international varieties like Cabernet Sauvignon and Merlot that consistently push the boundaries of Italian wine excellence.
But how did the wine suitcase actually handle the rigors of the Tuscan terrain and travel?
“Suitcase performed well today. Took the train to Florence and headed to Tuscany. Added a few more bottles and let the suitcase even tour San Gimignano” – Curt
San Gimignano is a striking medieval hill town famous for its iconic skyline of soaring stone towers, winding streets and remarkably preserved historic architecture. Often called the “Town of Fine Towers,” this gem sits amid rolling countryside that serves as the exclusive home of Vernaccia di San Gimignano—a crisp, historic white wine celebrated since the Renaissance.
Phase 3: Reaching Full Capacity – March 1–2, 2026
By March 1, the suitcase had hit its ultimate challenge: maximum payload, featuring a very special (and nerve-wracking) addition.
“A quiet day for the wine suitcase as we have an apartment, but I have brought the load from today home and it is time to fill. Only problem now is a full suitcase! In this case is the most expensive bottle I have ever purchased….damn you wine suitcase for making it so easy.” – Curt
Packing 12 bottles of wine into a piece of luggage sounds like a logistical nightmare, and for good reason. A full dozen standard wine bottles adds roughly 33 pounds of dead weight to a bag, pushing total loads right up against strict airline weight limits while putting massive, structural stress on cheap frames, zippers and, most importantly, the wheels. Most conventional travel suitcases quickly buckle, bow or blow out their zippers under that kind of concentrated pressure. But the 12-Bottle Wine Suitcase is built specifically for the oenophile, utilizing a high-density, zero-shift foam insert and a reinforced proprietary shell designed to absorb the heavy lifting without breaking a sweat. Despite being fully loaded, the case continued its leisurely tour of the region the next day while handling some famously rugged Italian terrain.
That kind of heavy-duty reliability changes the entire travel equation. Instead of constantly stressing over baggage handling or wondering if your prized vintage is going to arrive as a high-end salad dressing, you get total peace of mind. As Curt and Joy quickly discovered, rolling through bustling rail stations and rugged European streets with a fully loaded mobile cellar isn’t just manageable—it is downright effortless.
“Works very well. A lot of the streets are cobblestone/brick and the wheels do great. Started in Milan…train to Florence and 2 days in the San Gimignano region (primary specialty grape is Vernaccia). Today, Chianti region (primary grape Sangiovese).” – Curt
“Although the suitcase is full….it is still fully enjoying its tour of Tuscany” – Curt
After a couple of busy days hopping between medieval towers and rolling hills, March 3 brought a welcome change of pace. Not every travel moment needs to be broadcast to the world, and sometimes the best part of a trip is simply putting the phones away, living in the moment and enjoying a quiet glass of Sangiovese without narrating it. But rest assured, the suitcase was resting up for its grand finale.
After all, even a hard-working mobile cellar deserves a day off to soak in the slow rhythm of the countryside before the pace picks back up. With batteries recharged and legs stretched, the suitcase was more than ready to trade quiet vineyard views for the adrenaline-fueled rush of high-speed rail.
As March 4 rolled around, it was time to transition from the slow cadence of Tuscany back to the fast lane. Curt and Joy prepared to catch the high-speed rail back north. Will the Fly With Wine Suitcase keep things intact?
Phase 4: High-Speed Homeward Bound – March 4–5, 2026
If cobblestones are a test of a suitcase’s wheels and frame, high-speed rail is the ultimate test of durability and bottle protection.
“When one travels with a wine suitcase…it is important that your wine travels well. Welcome to 186MPH….Florence to Milan” – Curt
With the high-speed dash behind them, Curt and Joy wrapped up their itinerary on March 5, bringing a fully intact, prized collection safely back home.
“The wine suitcase on its final train journey. It has performed great and is easy to maneuver when full! Thank you for letting us use it!!” – Curt
The Verdict
Curt and Joy’s trip proved everything we love about the Flies With Wine suitcase. Whether it’s gliding smoothly over ancient cobblestones, holding up under the weight of a collector’s most prized bottles or surviving a 186-MPH train ride across Italy, it delivers absolute peace of mind for the traveling oenophile.
Traveling with your favorite vintages doesn’t have to be a guessing game, and if you’re ready to secure your own gear for your next adventure, we have a perk for the community! As a Wine Time Fridays listener, you can score 20% off all VinGardeValise products (the parent company behind the ultimate wine suitcase) by shopping through this link and using code X9VTNWP at checkout. (Note: This special 20% discount applies specifically to VinGardeValise products.)
We want to thank Curt and Joy for allowing us a peak into their Italian adventure and to you for reading! Keep in mind that this Fly With Wine Suitcase is the lesser expensive product line of VinGardeValise and it it held up magnificently! If you want to hear from the CEO of VinGardeValise, Brooke Kochman, check out episode 306 of our Wine Time Fridays podcast!
The Ultimate Italian Test Drive: Putting the “Flies With Wine” Suitcase Through Its Paces
