Off the Beaten Path in Northeastern Italy


From the magical, lost-in-time city of Trieste to the vineyards of Gorizia and mountain paradise above Tarvisio, we’ll explore the hiking trails, culture, and history of the Friuli Dolomites—a delightfully untouristed corner of northern Italy, with a slice of Slovenia to boot! We follow coastal trails above the enchanting Bay of Trieste to Duino Castle, where poet Rainer Maria Rilke wrote the haunting Duino Elegies, and wander the ancient streets of Aquileia, the city that was second only to Rome at the height of the Empire, discovering the exquisite mosaics of the massive 3rd century basilica. In the rolling hills of the Collio, the trail leads right from our 13th century castle-hotel to the high vineyards of this renowned wine region, and we’ll explore historic Palmanova, with its star-shaped fortress walls and intriguing Cividale, the first capital of the mighty Lombard Kingdom, and dine at Joe Bastianich’s beloved Orsone.

A quick hop across the border brings us into Slovenia, yet we’re still in the historic Friuli region. In Kobarid, we’ll hike mountain trails that pass by WWI bunkers that once sheltered Italian troops during the epic siege along the Isonzo Front, immortalized by Hemingway in A Farewell to Arms, one of his most beautiful novels. Our dinner in Kobarid is at Hisa Franko, the renowned restaurant run by Ana Roš, who was named the world’s best female chef in 2017. Back in Italy, top of the world hikes take us to crystalline lakes, mountain refuges, high alpine pastures beneath rugged peaks, and a 16th century mountaintop pilgrimage site. Trip Leader Gianluca Canalicchio is a dedicated foodie who ensures that his hiking adventures always include memorable meals. Our grand finale is in Venice, where we stay right on the Grand Canal, have our own private tour of the canals, and visit one of the city’s most famous palaces. Hiking, culture, history, renowned cuisine—this new adventure in an uncrowded corner of northeastern Italy has it all.

Itinerary at a Glance

Day 1
Discover Trieste / Hike the Napoleon Way

This magical but off-the-beaten-track city was the foremost seaport for the great Hapsburg Empire. We get a glimpse into its magnificent history at the grand Piazza della Republica, one of the world’s most beautiful seafront piazzas. Hike the Napoleon Way along the coast high above the Bay of Trieste and explore the historic city center on foot, then overnight at the Grand Hotel Duchi d’Aosta. Our Welcome Dinner is right downstairs at Harry’s Bar.

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Day 2
Village-to-Village Hikes / The Osmiza Experience

On the nearby karst plateau, famous for its production of wines like the robust Terrano and fruity Malvasia, we’ll hike village to village and sample local beverages when we relax for lunch at an osmiza, where sausages, olives, cheeses, and local wine are served right on the premises of the farmers who produce them. We enjoy an aperitif at one of Trieste’s historic coffeehouses before dinner.

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Day 3
The Rilke Trail / Duino Castle / Ancient Aquileia

We set off along the stunning Rilke Trail above the Adriatic to Duino Castle—where Ranier Maria Rilke stayed when he wrote his inspiring collection of mystical poems—and see the same rugged coastline and unspoiled woodland that inspired him. After lunch by the castle we head to Aquileia, a UNESCO World Heritage Site with a stunning 3rd century basilica. We overnight in the 13th century castle at Spessa (Casanova stayed here!), where we’re welcomed with a drink in the spectacular wine cellar.

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Day 4
The High Vineyards Trail / The Walled City of Palmanova

After breakfast in the castle kitchen we hike across undulating countryside along the Sentiero delle Vigne Alte, through the lush vineyards and stop for lunch beneath a leafy arbor at a typical Friulian osteria. We’ll see craft vinegar production from local grapes, then discover Palmanova, a fortress city protected by massive ramparts in the shape of a nine-pointed star. Dinner tonight is at Orsone, created by award-winning mother-and-son restaurateurs Lidia and Joe Bastianich.

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Day 5
Cividale to Slovenia / Farewell to Arms / Hello, Phenomenal Cuisine

We walk into Cividale del Friuli, crossing "the Devil’s Bridge" and visit its ancient and haunting chapel, famous for its depiction of six solemn and mysterious female saints. After lunch on the piazza we slip across the Slovenian border to Kobarid, where we hike through deep forests, past waterfalls, and along a broad canyon. Here we gain insight into WWI as we pass bunkers carved into the hillsides by Italian soldiers during the brutal bombardments of the siege of the Isonzo Front. This evening we’re treated to a special 11-course tasting menu at Hiša Franko, where the chef, Ana Roš, was named the world’s best female chef of 2017.

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Day 6
Glacial Lakes / Mountain Refuge / Hiking the Friulian Dolomites

A short drive across the dramatic Predl Pass brings us back into Italy and the spectacular Fusine Lakes—the starting point of our hike. These crystal-clear, glacial beauties lie in a limestone amphitheater where spruce forests give way to the steep, wild ridge of the Picco di Mezzodì. After lunch on the lake’s edge we hike up to Rifugio Zacchi for a sweeping panoramic view of the rampart of mountains.

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Days 7-8
Hiking to the Top of the World

On Day 7 we hike through pine-scented forests up to the Montasio Plateau—a true Top of the World adventure! Cows grazing in the bucolic landscape produce milk for famed Montasio cheese, produced here since the 1200s. This afternoon we stop in the charming village of Malborghetto and the 17th century Palazzo Veneziano, enjoying a coffee and pastry on the tiny village square. On Day 8 we hike up Monte Santo di Lussari, a pilgrimage site where the 16th century chapel gives us sweeping views into Slovenia, Italy, and Austria.

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Day 9
Exploring a Palace and Hidden Canals

Our fabulous 4-star hotel, the Palazzo Giovanelli, is situated right on Venice’s Grand Canal. We walk alongside canals and over bridges to explore Ca’ Rezzonico palace, a splendid example of baroque and rococo architecture and "Museum of 18th century Venice," where we’re immersed in the romance of trompe l’oeil ceiling frescoes, Murano glass chandeliers, and elegant furnishings. This evening we cruise on a private vaporetto, passing through charming small canals. Our Farewell Dinner is on an intimate piazza.

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Day 10
A Farewell to Venice

This morning a water taxi takes us to the train station at Piazzale Roma on the edge of town. From here guests can continue by bus to Marco Polo Airport or by train to other destinations in Italy.



Explore the two magical cities, Trieste and Venice, stay in historic castles and palazzos
Hike through the enchanting vineyards of the Collio, explore Roman Aquileia and the fascinating Cividale
Discover the Friulian Dolomites, with top of the world hikes in Slovenia and Italy
Experience WWI history in Kobarid, dine at renowned Hisa Franko, named one of "the Top Restaurants in the World"
Follow coastal trails above the Adriatic to historic Duino Castle, in the footsteps of Rilke
Savor regional cuisine and wine with Trip Leader Gianluca Canalicchio, a devoted foodie


Length: 10 days
Cost From: $5695  
Arrive: Trieste, Italy
Depart: Venice, Italy
Lodging: 4 nights in charming mountain hotels; 5 nights in historic properties
Meals: All meals included except 1 dinner (B=Breakfast, L=Lunch, D=Dinner)
Activity: Cultural Adventures, Hiking / Trekking
Trip Level:

Moderate hikes, from 1-5 miles daily, on coastal or steep trails