Even in a country of such rustic charms, the village of Asolo stands out: its numerous surrounding peaks gave it the nickname “City of a Hundred Horizons,” while its streets are a pleasant jumble of medieval and early Renaissance architecture. Your boutique hotel in the heart of the city embodies all of Asolo’s appeal, while a traditional village restaurant hosts your welcome dinner, serving up authentic local specialties.

The Prosecco region has been renowned for viticulture since Roman days, its horizon-spanning vineyards lending symmetry to the rolling hills, with centuries-old villas and manor houses rising like islands amid the vines. At family-owned Villa Sandi, named one of the World’s Best Vineyards in 2023, try some of its best-loved varietals, including sparkling Asolo Prosecco Superiore DOCG Brut and its versatile red, the Raboso Marca Trevigiana IG. Its beautiful villa is a Palladian masterpiece dating back nearly 400 years, its classic elegance undimmed. Villa Sandi wines further accompany lunch in nearby Locanda Sandi, where traditional dishes on offer might include Locanda snails, slow-cooked sopa coàda, or meat grilled on the restaurant’s open fire. Rosapetra, your home for the next three nights, shows off Cortina spectacularly, each room harmoniously blending rustic Alpine charm with windows and balconies that open onto epic views of the surrounding mountains.

Jagged here and squared off there, the Dolomite mountains are irresistible to skiers and snowboarders in winter, while in summer, their retreating snow cover beckons hikers and climbers in search of panoramic landscapes not found anywhere else. Ascend along winding roads by Jeep and on foot for a view of five peaks so stunning UNESCO recognized them as part of the world’s natural heritage: the Cinque Torri (Five Towers). Walk around the open-air Museum of the Great War, at the foot of the Marmolada glacier, the site of high-altitude battles. Head to Rifugio Scoiattoli for lunch, set high on the slopes overlooking the Cinque Torri, where over homemade pasta, a seasoned climber joins you to share stories of scaling these slopes and peaks.

Cortina is justly known as “the Queen of the Dolomites,” a town that complements its sweeping surroundings with high-end shopping, fine dining spots and quaint Alpine architecture, not to mention delectable local goods, which you discover firsthand with a morning visit to a local cheese house. Meet the cheese maker and descend to the cellar to taste just-ripe cheeses right where they age, a glass of local wine in hand to wash it down. The afternoon is reserved for your choice of activity in this breathtaking spot, with options including paragliding, a helicopter tour, tennis or a hike or cycling excursion as challenging or relaxing as you like. Tonight’s dinner is set in Alajmo Cortina, where traditional mountain fare is served up with an exciting contemporary twist. 

En route to Venice lies the Vajont Dam, where in 1963 a landslide led to a catastrophic flood that swept away many of the surrounding villages and towns. The dam remains today, decommissioned but still among the tallest in the world, and a powerful symbol of remembrance for the Italian people. A local expert paints a vivid picture of the event and explains what led to it. Later, toast your arrival in Venice with a cocktail in lively Saint Mark’s Square. Your hotel, Palazzina Grassi, is one of the best in this remarkable city: a Philippe Starck-designed boutique hotel, elegantly modern and unmistakably Venetian, that has hosted Hollywood royalty.

Rising from an enclosed lagoon on the Adriatic Sea, Venice is a byword for Old World romance and charm, from intricate Italian Gothic architecture to the iconic gondolas and vaporettos passing under the bridges that delicately span its canals and waterways. A private launch brings you to the Cannaregio district, home to one of the town’s most spectacular and best-kept secrets: the furnace of Angelo Orsoni. The oldest of its kind in the world, it has been producing precious glass and gold mosaics since 1888. Watch artisans up close as they create the kind of masterworks that adorn Westminster Abbey, the Golden Buddha in Bangkok and the Theatre de l’Opéra de Paris. Later, an expert guide leads you on a stroll through the historic Jewish neighborhood to the Rialto Bridge.

In the heart of Venice on the Grand Canal sits the Palazzo Erizzo Nani Mocenigo, an iconic building constructed in 1480 in Venetian Gothic style. Now home to the Ligabue family and housing part of the private collection of the Ligabue Foundation, the doors of this private palace are opened exclusively for you this morning. Tonight’s farewell dinner at a lauded local restaurant caps this immersive exploration of northeastern Italy.

Transfer by boat to the airport and depart.