When our good friends Curt and Joy Grady headed to Italy for a whirlwind trip from February 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!
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!
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.
“Suitcase performed well today. Took the train to Florance and headed to Tuscany. Added a few more bottles and let the suitcase even tour San Gimignano” — Curt (Accompanied by 4 travel and destination photos)
“Tuscany is a hideous place…🤣” — Curt (Accompanied by 5 stunning photos of the Tuscan countryside)
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
Despite being fully loaded, the case continued its leisurely tour of the region the next day while handling some famously rugged Italian terrain.
“Although the suitcase is full….it is still fully enjoying its tour of Tuscany” — Curt
“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
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.
(Stay tuned for more gear reviews, wine finds, and podcast updates right here on the blog!)
The Ultimate Italian Test Drive: Putting the “Flies With Wine” Suitcase Through Its Paces
