Italy Cruises


See More of Italy in Private Yacht Style


Let Windstar’s Italian cruises whisk you away to charming villages, pristine beaches and legendary cities with unique itineraries that let you discover Italy as it was meant to be seen. From the picturesque pastel towns that line the Amalfi Coast to enchanting islands such as Sicily and Elba, you’ll explore breathtaking sights in charismatic small ports and beautiful hidden harbors without missing the remarkable history of larger cities such as Rome or Venice. Discover a more intimate Italy by day and unwind back onboard with the pampered, personalized touch of Windstar Cruises.

 

Rome to Venice - 8 Days

Explore the shores of Italy, Croatia and Montenegro, discovering the charm of Venice, the magnificence of Rome, and the vast beauty of the Dalmatian Coast. Wander down the ancient cobblestone streets of Taormina, travel up the sparking fjord to Kotor and bask in the allure of small ship cruising as your small ship anchors in the heart of Old Town Dubrovnik while larger ships only pass by. From remarkable small ports such as Rovinj to timeless cities like Venice and Rome, discover the Mediterranean’s most charming and historic destinations in one incomparable voyage.

Rome to Rome - 10 Days

Encircle the Isle of Sicily and discover sparkling resorts favored by emperors, towns frozen in time by legendary volcanoes, Maltese palaces where knights and Grand Masters once gathered … this itinerary has them all. Watch the stunning Amalfi Coast pass by from the deck of your intimate small ship and raise a glass of limoncello to another blissful day in the warm Mediterranean sunshine.

Rome to Venice - 11 Days

Treat your palate to savory Balkan burek, and pizza as only Sicilians can make it. Relive medieval days in the Old Towns of Dubrovnik, Piran, and Kotor. Wonder over the beehive-like trulli and elegant seaside towns of Puglia. Lose your heart to Sorrento and the Amalfi Coast, the song of a Venetian gondolier, the ceiling of the Sistine Chapel. Stand at the rail with Chianti in hand as white sails unfurl above you, carrying you across the sparkling Mediterranean in private yacht style.

Rome to Rome - 10 Days

Delight in la dolce vita as you cruise the Italian Mediterranean on the elegant Wind Surf, tipping your hat to the other yachts as you visit ports where only small ships go. All the stories you’ve heard about the breathtaking coastlines of Amalfi and Cinque Terre? They’re all true. Feel your heart soar in the presence of Michelangelo’s David in Florence or the haunting ruins of Pompeii. Bear witness to Italy’s protracted genesis as you cruise past Stromboli, view Mount Etna from the Roman amphitheater in Taormina , swim in the hot springs-heated seas of Vulcano Island , and gaze across the Bay of Naples at Mount Vesuvius. Dream of Caesars in Rome, walk the hills of Corsica in the footsteps of Napoleon, stand on the Square of Miracles  in Pisa like Galileo as the Leaning Tower continues to hold gravity at bay.

Rome to Nice - 7 Days

Live the dream of the Italian and French Rivieras. It feels like you’re on your own private yacht in a yachtsman’s paradise. From the tiny villages of Cinque Terre to the chic style of Monaco and Cannes, let Windstar show you the legendary ports of the world’s most privileged yachts. Sparkling cities, ancient treasures, tranquil beaches, stunning coastlines.

Barcelona to Rome - 7 Days

Enjoy the world’s premier yachting playgrounds in a beautiful small ship that feels like your own private yacht. These beautiful ports string together like perfect pearls, each glowing with its own special beauty. Sparkling cities and charming villages. Secluded harbors and immaculate beaches. Discover the mystique and magic of the Rivieras that only an intimate small ship can show you.

Venice to Venice - 10 Days

The romance begins in Venice—the city of lights, of water, of bridges—with an overnight stay that offers up all its treasures to you. In the days ahead, fall in love again and again as you explore the Balkans with their red-roofed medieval cities and turquoise travertine cascades, and the roads less traveled on Italy’s rustic east coast. Savor each splendid moment of the journey up the scenic Bay of Kotor. Inhale the aroma of orange and lemon trees from Corfu. Puzzle over the strange conical-roofed trulli of Alberobello and the cave-town of Matera in Puglia. Return to Venice wishing you could do it all again.

Rome to Rome - 7 Days

Cue the accordion music and say arrivederci to Rome as you embark on this 7-day tour through Western Italy. Arrive in Sorrento to stunning views of Mount Vesuvius and the lovely Bay of Naples, with an extended day ahead to fill with an excursion to Pompeii or Capri. Discover Sardinia’s 28 blue-flag beaches and Bronze Age settlements, and explore the surprisingly unspoiled northern region  of Corsica. Linger in Portofino late into the evening, soaking up delicious views of the Italian Riviera and an incredible sunset that paints the pastel cliff villages neon. Climb the 414 steps of Giotto’s bell tower in Florence, arriving breathless not just from the effort, but from the view. Return to Rome, a city that begs you to stay and explore more than 3,000 years of history.

Barcelona to Rome - 7 Days

Hidden harbors. Legendary landmarks. Everything that makes the Mediterranean magical. This voyage has it all. The colorful kaleidoscopes of Rome and Barcelona invite you to celebrate their high-spirited energy, while the seductive scent of oranges and olives that perfumes the enchanting islands of Elba, Corsica, Mallorca and Menorca entices you to explore their seductive secrets. From the wild green mountains of Mallorca to the striking white pebble beaches of Portoferraio – let us delight your senses and ignite your imagination.

A perfect blend of antiquity and artistry, this 14-day cruise sails from the ancient ruins of Athens and makes a dozen port stops in Greece, Italy and France before disembarking among the contemporary architecture and gleaming, cosmopolitan wonders of Barcelona, Spain. Stroll the narrow streets inside the concealed medieval walls of Monemvasia, Greece and take an exhilarating tour of Corsica’s narrow winding coastal roads outside Calvi, France. From the Greek and Roman funerary steles - ancient marble reliefs depicting venerable people engaged in everyday life - to the vibrant and radiant impressionist paintings and dizzying mosaics of Antoni Gaudí’s Barcelona architecture, this is an ideal journey for passionate historians, art lovers and all seeking unforgettable cultural immersion.

Barcelona to Rome - 17 Days

Indulge in unhurried pleasures among steep coastal cliffs, tiny vineyards and romantic villages throughout the Rivieras and Western Italy during this 17-day, autumn cruise. During the fall winemakers are racking fresh wine into barrels, and new olive oils are sampled for the first time. Stroll uncrowded avenues and discover fresh, distinctly nutty porcini mushrooms served fresh on pastas and sautéed into tapas at sidewalk cafés, browse open markets and inhale the fall aromas from ripe apples, plump grapes and early season citrus. Test your luck in a Monte Carlo casino, hike the desolate Crateri Silvestri on the southeast slope of Sicily’s Mount Etna, and learn about Malta’s noble heritage inside the precipitous medieval walls of 4,000-year-old Mdina — The Silent City.

Rome to Barcelona - 14 Days

Steep orange cliffs bathed in the afterglow of an early summer evening, bright alabaster beaches caressed by azure seas, breathtaking vistas high above verdant olive groves and mosaic-like red terracotta roofs. Discover new perspectives and the true colors of the Rivieras during this 14-day cruise of small ports and stunning overlooks throughout Italy, Monaco, France and Spain. See the island of Elba through the eyes of exiled Emperor Napoleon Bonaparte as you explore his historic residence near Portoferraio, Italy. Walk or ride along portions of the Grand Prix circuit in Monte Carlo, one of the most prestigious and glamorous race courses in motor racing history. When you’re ready to relax, sample family-crafted French wines and olive oils from century-old trees as you take in the views from the Provençal hilltop village of Le Castellet near Sanary-sur-Mer.

Venice to Barcelona - 15 Days

Discover the culture, history and cuisine on both sides of the Italian peninsula during this 15-day cruise of the Adriatic, Ionian, Ligurian and Tyrrhenian seas. This back-to-back cruise is ideal for optimizing shore excursion time in Italy, Croatia, Montenegro, Monaco, France, and Spain without a single sea day. Stroll through Roman ruins in Rovinj, Croatia, sample olives and smoked hams at a centuries-old family farm in Montenegro, or savor an unforgettably romantic evening dinner at Château Eza in Èze 1,400 feet above the beaches of the French Rivera.

Italy alone cultivates more than 350 known grape varieties for remarkable and award-winning wines, so spend some extra time familiarizing yourself with regional cuisines, distinct beverages and unique customs during this 17-day cruise from Barcelona, Spain to the French and Italian Rivieras and wayward ports on Sicily and Malta. Beyond vino is a delightful array of other attractions to experience, including the silent Greek ruins of ancient Syracuse on the island of Sicily, and a memorable Maltese working farmhouse where you’ll collect savory and diverse herbs for a cooking lesson and rustic rural meal.

Venice to Rome - 18 Days

Discover the Adriatic, Ionian, Ligurian and Tyrrhenian seas during this 18-day cruise around the Italian peninsula as you explore ports in East Italy, Croatia, Montenegro, West Italy and France. Kayak along Dubrovnik’s old city walls, swim or snorkel in Kotor Bay in Montenegro and make your own Sicilian-style pizza on Lipari Island. Explore the ruins of Pompeii as you gaze skyward toward the summit of Mount Vesuvius, and savor tangy mulberry gelato in the shade of the Roman walls that still protect the 3rd  century village of Taormina near Messina.

Thank You!

We'll send you the latest deals to your email.

Click here to view our current special offers.

ok