Day 1: Trieste

Benvenuto to Trieste, a cosmopolitan port city with wide boulevards and grand Habsburg architecture – a reflection of Trieste’s history as part of the Austrian Empire, giving it a graceful central European feel, culturally more Balkan and Austrian than Italian. We’ll meet up with Bobby at our hotel, the impeccable Grand Hotel Duchi d’Aosta, on the waterfront in the heart of Trieste’s old city. From there, we set off to explore the city, taking in some of Bobby’s favorite sights followed by a toast with wines selected by Bobby from the surrounding Friuli-Venezia Giulia region.

Dinner tonight is at Trieste’s only two Michelin star restaurant, Harry’s Piccolo, literally in our hotel. It’s an intimate celebration over seven courses of Friuli-Venezia Giulia’s finest ingredients — langoustines and wild sea bream from the Adriatic, produce and cheese sourced daily from local farms. It’s a passion for the freshest ingredients and the finest wine that we’ll encounter over and over again in Friuli. It’s the perfect introduction to the region, and the ideal start to our  journey together.

Day 2: Trieste

Breathe in the aroma of freshly ground coffee in one of Trieste’s best brew houses, served in a private tasting room with a behind-the-scenes look at perfecting a cup of Italy’s finest caffè.

Next, we’ll point our compass toward Carso, past rows of mature vines painting the hillsides. At Vodopivec Winery we’ll have the rare opportunity to taste Vitovska, an ancient greenish-gold grape; owner Paolo Vodopivec works exclusively with Vitovska in his 15 acres of vineyards. He’s an organic producer and advocate of using buried amphorae as fermentation vessels; nearly all Vodopivec wines spend a minimum of 12 months in subterranean amphorae. Paolo will lead us through the winery and on a private tasting of his varietals, perfected over generations. 

After lunch, we return to Trieste for an exclusive visit to the city’s marquee Castello di Miramare, commissioned by Archduke Maximilian of Hapsburg, and worthy of his name and rank. The 19th-century palace overlooks the Gulf of Trieste in neo-Gothic majesty; we’ll be guided through it by our own art historian.

Day 3: Cormons

We dedicate our morning to the sea: first, by private boat as we cross the gentle azure waters of Grado lagoon to Isola di Anfora. Then, on this speck of an island barely 200 meters wide, we’ll sit down to lunch at Trattoria ai Ciodi where Cristiano Tognon and family serve the freshest seafood — caught, in many cases, just offshore— in a lovely garden setting.

From Grado, we’ll spend a hour or two exploring the ruins of Aquileia. One of the early Roman Empire’s largest and wealthiest cities, Aquileia was destroyed by Attila in the mid-5th century and still, today, lies mostly unexcavated beneath the fields. An archaeologist leads us through this stunning UNESCO World Heritage Site.

In Cormons, we’ll check in to La Subida and settle in to our private cottages, enveloped by the scents and scenes of the surrounding forest. Dinner tonight is at La Subida’s own Michelin star kitchen, Trattoria al Cacciatore, helmed by Chef Alessandro Gavagna. His menu spins tradition on its head with dishes like tortellini filled with partridge and chocolate, and an elevated version of Friuli’s classic peasant dish toc’ in braide.

Day 4: Collio

Collio, on the border of Slovenia, is one of Bobby’s most cherished wine regions. The distinct terroir starts with the signature ‘Ponca’ soil: sandstone and marl rich in clay and silts, cooled by Adriatic Sea breezes in summer, and sheltered by the Alps in winter. The resulting white wines of Collio are bold and rich, highly textured — and highly prized.

Ronco del Gnemiz has been one of Friuli-Venezia Giulia’s leading wineries for more than a decade. Here we’ll meet Bobby’s friend and winemaker, Christian Patat, for a personal tour of the hilltop winery, tasting one of the world’s great Sauvignon Blancs and the native red Schioppettino. 

For lunch we meet another friend of Bobby’s, winemaker Andrea Felluga, who opens the door to his family home for a country feast paired with Picolit and Friulano varietals, and refined blends like Terre Alte and Abbazia di Rosazzo, from his Livio Fellugo winery. 

In the evening fourth-generation vintner, Giampaolo Venica, leads us through Venica&Venica’s bucolic rolling vines, tasting as we go. Our private cellar dinner here celebrates the remarkable wines of Collio.

Day 5: Udine & Slovenia

After breakfast we’re off to Udine, all cobbled streets and painted pastel facades. The drive through the Friulian countryside leads us to a 19th-century farmhouse, Borgo Nonino, for an appreciation in the art of grappa riserva — the traditional digestivo‘s barrel-aged, distinctly elevated form.

In Udine we pay homage to one of Italy’s most renowned artists and arguably the greatest painter and frescoist of the 18th century, Tiepolo, with private access alongside an art historian to his masterpieces hanging in the halls of 16th-century Casa Cavazzini. After a lively osteria lunch, we’ll have the afternoon to explore Udine on our own.

A sunset aperitivo sets a joyful mood as we head for an unforgettable dinner adventure over the border in Slovenia. At two Michelin star Hiša Franko, Chef Ana Roš doesn’t adhere to any particular culinary style. She’s a self-taught chef with a simple philosophy: follow nature, take what the seasons offer, don’t be afraid to take risks.

Day 6: Sauris & Venice

We lift off this morning in private helicopters, gliding smoothly over the jagged peaks of the Friulian Dolomites. Our destination is the village of Sauris, nestled in a valley dense with fir and beech trees. Here, for three generations, the Petris family has crafted prosciutto di Sauris, lightly smoked fiocco and soppressa, pancetta and salsiccia. We’ll have a behind-the-scenes look and sample some of Italy’s finest cured meats.

Among Friuli’s formaggio, Montasio DOP, made exclusively from cow’s milk, is highly prized. We’ll meet local cheesemakers and journey with them up to a malghe (mountain hut) where cows graze under the cool breezes sweeping down from the peaks.

For lunch we are hosted by the Schneider family, friends of Bobby’s and owners of Alla Pace. This Michelin-recommended kitchen occupies a noble mountain villa that’s been in the family since 1804. We’ll sit down for a true Alpine feast: smoked ricotta, freshly foraged mushrooms, pitina slowly smoked with pine embers.

From here, it’s on to Venice. We’ll drift down the mountain through pristine wine country and watch in awe as the pastoral landscape gradually gives way to one of the most enchanting cities in the world.

We’ll join Bobby for a sunset aperitivo at the Aman, and then take the evening to explore Venice on our own. 

Day 7: Venice

Yesterday, we began with a helicopter. Today, we go by boat.Few places are as mesmerizing, intoxicating as Venice. There’s beauty everywhere in this city of winding waterways and grand architecture in garish reds, muted yellows, and bright blues. 

We’ll join Bobby on a personal exploration of his favorite spots, tucked along the canals and hidden in quiet courtyards, stopping for a brief visit to the garden and vineyard at San Francesco della Vigna. Then it’s back to the water as we sail past the iconic Venitian Aresenal to accept our private invitation to enjoy an apertif at one of Venice’s most stunning renaissance-era palaces.

The afternoon is yours to enjoy our hotel — the Aman Venice is an oasis of tranquility, in a 16th-century palazzo overlooking a serene garden terrace and the Grand Canal — or dive deeper into Venice.

We’ll reconvene with Bobby for a spectacular celebration of our time together: a private dinner in one of the Aman’s ‘hidden’ salons, impressively frescoed and lit by grand chandeliers with outstanding views. Dinner is a multi-course feast for the senses crafted by legendary Chef Norbert Niederkofler of three Michelin star St Hubertus in San Cassiano. It’s our last night, so of course we’ll celebrate with the finest wines and toast Bobby, each other, and this incredible journey.

Day 8: Departures

Alas, our journey together has come to an end. After breakfast we’ll say farewell to Bobby, and transfer to Venice Marco Polo airport to meet your departing flight. 

During our eight days in Italy, we’ve been welcomed into the homes, vineyards and cellars of Friuli-Venezia Giulia, alongside Bobby and experiencing this unparalleled wine region in ways no other travelers can. We hope as you go forward in life, that this truly special experience stays with you, a reminder of the essential truth that often gets lost in the shuffle—that the world is a beautiful place and that we humans are, indeed, limitless, and full of hope, joy, audacity and light. Until next time!