Gondolas are an iconic symbol of Venice, and the local gondoliers take great pride in their vessels and their craft as they navigate the waterways in a city of labyrinthine canals and historic bridges. This means of transportation dates to the 16th century and was designed specifically for the Venetian lagoon. Climb aboard your sleek gondola and let the expert gondolier take you on a marvelous journey through the ornate palaces, grand cathedrals and iconic squares that line the canals of Venice.

After strolling past the eateries, and shops of the Dorsoduro district, stop to take in the views of Squero di San Trovaso, the oldest and most picturesque of Venice’s three surviving boatyards. Not far from the historic boatyard, enter the famous Gallerie dell'Accademia for a guided tour of its celebrated collection. Behold the Legend of Saint Ursula, by Vittore Carpaccio, a cycle of nine magnificent paintings from the late 15th century.

There is only one place in the world where dorona di Venezia grapevines grow, and that is the Venissa wine estate, a 2.5-acre plot of land seasoned by the salt waters of the Adriatic on the tiny island of Mazzorbo. Cruise across the sparkling Venetian Lagoon for a one-of-a-kind experience at this unique vineyard resurrected over the past few decades by the Bisol family, famous for producing prosecco di Valdobbiadene since the 16th century.

For centuries a center of culture, Venice has a rich heritage in the performing arts, as you’ll explore on this excursion. Transfer from the yacht by private launch to Saint Mark’s Square. From there you’ll walk to the Teatro La Fenice, which first opened in 1792 and was renowned throughout Europe in the 19th century for staging operas by the best composers of the day. Although it has burned down at least three times, most recently in 1996, Venice’s beloved opera house has been restored to its 19th-century grandeur.

Sicilian cuisine, like all regional cooking in Italy, begins with fresh, seasonal ingredients, so this tour starts with a drive south to the town of Giarre and its bustling, colorful market. Follow your guide down the aisles lined with the morning’s catch, mounds of vegetables and fragrant fruit and herbs whose sellers supply many of the area’s restaurants and hotels. From here you’ll turn inland to the village of Zafferana Etnea, between the volcano and the sea.

Perched on mountain overlooking the sea, the ancient town of Taormina has been enchanting visitors since the 19th century. The excursion begins with the scenic drive from the coast to the elevator that will transports you up Monte Tauro to the center of the town. From there your guide will lead you along the cobblestone streets, sharing the history of the peoples and civilizations – the ancient Sicels, Greeks and Romans, Byzantines, Arabs and Normans, among them – who have played a part here.

The mighty – and still very active -- volcano of Mt. Etna dominates Sicily’s eastern coast and has life here, as you’ll see passing through landscapes transformed by past eruptions on the drive the cable-car station on the southern slopes. In 15 minutes, you’ll be whisked up to 2,504 meters, where you’ll then transfer to four-wheel-drive vehicles whose expert drivers deftly navigate the rugged terrain up to 2,900 meters high. From here, the hiking adventure begins as you follow your guide along foot paths and narrow trails to the old lava flows that characterize the upper slopes.

Drive up from the coast to Castelmora, one of the most scenic villages in Sicily, perched high on a mountainside and crowned by the ruins of a castle. With your guide, stroll down the narrow medieval alleys that are rarely visited by non-Sicilians, soaking up the ambience and admiring its well-preserved churches and buildings. You’ll then drive to nearby Taormina, the resort town that has been a destination for well-heeled travelers since the 19th century. Enjoy a leisurely guided stroll through the medieval Old Town, stopping at key landmarks such as the 15th-century Corvaja Palace.

Sicily’s most famous and dramatic landmark, Mt. Etna, is best viewed from the area. It’s a short drive from the yacht to the helipad near Taormina where you’ll take to the skies for a thrilling aerial tour over the towering volcano. The helicopter will fly over the top, which stands at more than 3,300 meters. From above, you’ll have an unparalleled view of the many craters, some of which may be smoking, and the Valle del Bove, the horseshoe-shaped depression carved some 5 kilometers across and 1,000 meters deep into the volcano’s eastern flank.

From the Piazza Tasso, the vibrant main center of Sorrento, you will set off to discover the highlights of this resort town famous for narrow streets, artisan shops and dramatic history. You will visit the haunting, overgrown modern ruins of the nearby Valley of the Mills and explore the Basilica di Sant'Antonino, the final resting place for the patron saint of Sorrento. From the lovely courtyard of the San Francesco Cloister and the adjacent public gardens, admire picturesque views of Sorrento Bay.