While planning my trip in luxury to Tuscany to mark a milestone birthday, I knew I wanted to somehow see as much of the beauty and experience as much of what Tuscany has to offer. The problem I ran into was trying to see all of the breathtaking villages, do all the wine tastings, and soak in all of the beauty that the Italian countryside holds in less than a week. It's virtually impossible to even scratch the surface in such a short period of time.
During my Tuscan adventure, it was also important to mark this specific trip with a unique experience that was special and extra luxurious — something that would leave me, my family, and close friends in complete awe both during the experience itself and stay with us as a memory we would all share with others for years to come.
"I needed something that could compress all of Tuscany into one extraordinary morning. I found it 2,000 feet above the vineyards."
Enter Wine in the Sky – Ballooning in Tuscany. A private luxury hot air balloon excursion for you and your loved ones — an experience you will never forget. This once-in-a-lifetime event is a joint partnership between the acclaimed Avignonesi Winery in the heart of Tuscany and Ballooning in Tuscany, the number one balloon ride company in the region.
Avignonesi had been on my radar for quite some time — specifically for their world-famous sweet wine known for its "Nectar of the Gods" characteristic. But the big surprise came when I arrived and tried the acclaimed Avignonesi-Capannelle 50 & 50. More on that later.
Ballooning in Tuscany offered larger balloons at a group rate if you wanted to share the experience, or a more intimate six-to-eight passenger balloon you could buy out exclusively. We opted for the latter. The exclusive experience for just our group of five was extraordinary. Here are the five highlights of the day, in the order they unfolded.
★ Highlight One
The Luxury Private Coach
Transport to and from the excursion was arranged by the remarkable innkeepers at our villa, Casa Portagioia — just outside of Castiglion Fiorentino, named the #1 Bed & Breakfast in the world by TripAdvisor three times running. We were picked up at 5am, approximately 90 minutes before sunrise, in an ultra-comfortable VIP coach that allowed our small group to rest during the 45-minute ride to Avignonesi Winery, arriving just before the sky began to change.
Casa Portagioia — three-time #1 B&B in the world, our home base in Castiglion Fiorentino
★ Highlight Two
The Balloon Experience
Upon arrival we were greeted by the accomplished balloon pilot — a man who conducts balloon tours all over the world year-round — and his impressive crew. We received a full briefing on what to expect, including how the chase car would follow us and collect us wherever we landed in the Tuscan countryside. He even invited us to help with the setup and stow-away process. Some assembly required — but it's actually an incredibly smooth and fun process.
After about twenty minutes of inflation, watching the balloon rise into the sky just as the sun began to touch the horizon, it was time for the magic. We each carefully loaded into the basket — plenty of room for our group of five and the pilot. With a few blasts of the burner and then complete, extraordinary silence, we lifted off.
The sun was peaking off one of the distant lakes as we ascended. Then there it was — fields upon fields of glorious vineyards, followed by even larger fields of sunflowers and ancient olive tree farms stretching to every horizon. Within minutes we had soared past the Avignonesi estate and out over the vast Tuscan landscape, villages with castles and cathedrals of all sizes rising up from small enclaves below. Our pilot expertly guided us over the most beautiful rolling hills any of us had ever seen, narrating landmarks as we drifted. Our hour in the air — covering at least twenty miles — felt like five minutes. We touched down in an open field, deflated and stowed the balloon together, toasted with a lovely glass of bubbles, received our official flight certificates, and were whisked back to the vineyard for the morning's next chapter.
5am at Avignonesi — the inflation begins as the Tuscan sky turns gold
Twenty miles of Tuscany in sixty minutes — vineyards, lakes, and ancient hills in every direction
Touchdown in a Tuscan field — followed immediately by a toast with bubbles and our official flight certificates
Watch the Full Experience
Wine in the Sky — the full 3-minute experience over Avignonesi
★ Highlight Three
The Brunch
Back at Avignonesi around 9am, our vineyard host and tour guide met us and escorted us through the impressive tasting rooms and into the magnificent outdoor dining area — set alongside rows of grapevines overlooking the countryside. Here, an exclusive brunch had been prepared just for our group by the executive chef of the winery. Private, unhurried, extraordinary. The flavors of Tuscany at their most essential — and a cappuccino that deserved its own standing ovation.
The tastes of Tuscany — morning cappuccino, truffle risotto, and a caprese that redefined the word "fresh"
★ Highlight Four
The Private Estate Tour
Immediately following brunch, our host led us on a private guided tour of the Avignonesi estate. Nestled between Cortona and Montepulciano, Avignonesi has become the leader in biodynamic viticulture — producing beautiful organic wines, maintaining the integrity of the grapes, and doing everything possible to live and work in harmony with the land. The tour walked us through the entire winemaking process from vine to bottle — across nine vineyard plots, the villa, the chapel, the historic wine cellars, and the unique aging cellar for their revered sweet wine. And then there was the haunted stairwell deep in the cave, left entirely "as is," for anyone who dares to climb.
Arriving at Avignonesi — the estate sits between Cortona and Montepulciano in the heart of Tuscan wine country
The dramatic tasting room entrance (left) and the ancient barrel caves beneath the estate (right)
★ Highlight Five
The Tasting
After the tour, we were led into the cellar tasting room where our extraordinary morning was topped off with four very special wines — including the revered sweet wine, and the one I had been dreaming about: the Avignonesi-Capannelle 50 & 50. A perfect red blend. OMG — there were fireworks. This is one of the very best reds I have experienced in years. Not surprising, given that the vintage I tasted retails for $150 and up. Thankfully, I walked away with two bottles at a gracious discount to relive the moment back home.
The Avignonesi tasting experience — the Classica collection laid out in a hand-crafted wooden presentation box
The 50 & 50 moment. I left with two bottles. Zero regrets.
Back in our private coach we went. Seven hours after leaving, we were back at Casa Portagioia by 1pm — in time to spend the rest of the afternoon by our lavish heated pool, taking in five-star views of the Tuscan hills. What an extraordinary day.
A few evenings later, one of those two bottles made its way to the birthday dinner table at Casa Portagioia. Every bit as extraordinary the second time.
If you're looking for the defining luxury experience during your Tuscan getaway, look no further than the Wine in the Sky excursion. It earns our coveted Five Star Seal of Approval — without question.
Five Star Seal of Approval
Wine in the Sky · Ballooning in Tuscany · Avignonesi Winery
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Ciao,
Patrick
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