Italy Cruises


See More of Italy in Windstar 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.

 

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.

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.

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.

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 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 Rome - 7 Days

Surrounded by glitterati on the glistening white Star Pride you fit right in; your insider’s experience at Monaco’s legendary Grand Prix the jewel in the crown of this exceptional cruise. Visit some of the world’s most glamorous ports — Portofino, St. Tropez, Sanary-sur-Mer, Monte Carlo — strolling famous promenades, shopping elite boutiques, and taking in world-renown beaches. Then during your overnight in Monte Carlo, enjoy exclusive access to special Windstar private Grand Prix events and two days of world-class Formula One® time trials and racing. It’s the ultimate expression of Windstar’s style, and open to only a very limited number of guests.

Barcelona to Athens - 10 Days

Set an unforgettable course from busy Barcelona to the silent ruins and relics high above Athens. Savor spicy tapas plates and fruity sangrias at a Palma de Mallorca beachside café. Delve into Bronze-age catacombs and learn Menorca’s strategic importance for Roman and Carthaginian trade. Visit a local winemaker’s Sardinian farmhouse and learn about Vermentino, Cagnulari, and Cannonau grapes as you sip and sample blends and vintages. Wander among imposing Greek statues and monuments in the Neapolis Archaeological Park outside of Catania, Sicily. Lean against the towering arches of Valletta’s Upper Barrakka Gardens as you take in breathtaking views of a fortified harbor unclaimed by centuries of kings and conquerors. This extraordinary passage along many Mediterranean island stops concludes in Athens, the cradle of democracy and Western Civilization. Take in the viewpoints from the Acropolis ruins over the city skyline or share your photos and memories in a quiet garden café among family, friends and grilled gyros paired with cool tzatziki.

Rome to Barcelona - 7 Days

Hidden harbors. Legendary landmarks. Everything that makes the Mediterranean magical. This cruise 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.

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 Windstar style.

Indulge your sense of adventure and slake your thirst for local cuisines and cultures during this 10-day cruise between Athens and Rome. Sail a Santorini catamaran around the volcanic islands of Thirassia, Nea Kameni and steamy newcomer Palea Kameni before swimming in relaxing thermal spring waters. Discover the untouched, windswept and often-overlooked island of Milos, the place where the storied Venus de Milo, one of the most celebrated statues in classical art, remained hidden for centuries. Transit the narrow, steep-walled Corinth Canal that divides the Peloponnese from the Greek mainland, an engineering feat attempted in antiquity, but incomplete for 2,000 years. Snorkel or sunbathe along the uncrowded beaches and clear waters near tiny Fiskardo. Master the fine art of Maltese Mediterranean antipasti platters and other culinary delights under the guidance of a professional chef. This remarkable journey ends in Rome, among the broken ruins of the Coliseum and Forum, the cradle of representative government. Wander narrow side streets and browse boutique shops for handmade souvenirs, but save a moment to throw coins in Trevi Fountain and guarantee future visits to this wondrous city.

Lisbon to Barcelona - 51 Days

Accomplishments of a lifetime deserve vacations of a lifetime, and this 51-day day cruise spanning the length of the Mediterranean is a perfect reward for milestones big and small. Depart from Lisbon and sail down the Atlantic side of the Iberian Peninsula where you’ll learn terroir secrets and the long history of sherry aging and sample dry, bready “fino” and dark, nutty “oloroso” sherries in the countryside outside Cadiz, Spain. Admire colorful mosaics and detailed stone latticework as you learn about kings and caliphs tied to the Moorish palace of the Alhambra above the port city of Almeria. Wander a medieval castle in Catania and learn how geology and nearby Mount Etna carried this coastal fortification nearly a mile inland. Listen to a private concert and attend an exclusive dinner among the towering pillars of the Celsus Library in the ruins of Ephesus, Turkey in our complimentary Destination Discovery Event. Wander the ancient baths, markets and forum at the excavated archaeological site of Pompeii. Stroll between century-old olive trees and vineyards surrounding an old French farmhouse outside Sanary-sur-Mer, then sample wines and olive oils in the intimate company of winery staff. Your epic odyssey ultimately concludes in the Catalonian capital of Barcelona, where you can board a cable car bound for Montjuïc Castle, or wind your way along Las Ramblas, an iconic, pedestrian mall lined with tapas bars, small shops and kiosk vendors. It’s an ideal way to find your own space to sip Catalonian Grenache red wine and reflect on your journey while tourists, shoppers and families flow by your table.

Complimentary Destination Discovery EventKusadasi: Evening in Ephesus

Athens to Venice - 8 Days

The timeless grandeur of the Acropolis and the volcanic vistas from Santorini’s blue-domed villages are perfect preludes to this detailed 8-day exploration of Greece and the Adriatic. Wander the elegant gardens surrounding the white-pillared Achilleion Palace in Corfu, an expansive summer home built by the former empress of Austria prior to World War I. Admire Monopoli’s 4,500-year-old urns and ancient artifacts, then stroll along the formidable walls of Castle of Carlo V, a pentagon-shaped fortification built to counter an emerging age of cannons and sails. Wander the uncrowded streets of tiny Komiza, then board a small boat and experience the azure and emerald iridescent magic within the limestone walls of the Blue and Green Grottos. Sit, sip and listen as Zadar’s shoreline waves create a concert of random music along the waterfront. This memorable journey culminates among Venetian gondolas and glass-blowers, where you can stroll with the pigeons in the Piazza San Marco or browse one-of-a-kind artisan shops featuring intricate jewelry or ornamental handmade masks.

Delve into architectural and epicurean wonders on both sides of the Italian peninsula during this 10-day adventure that combines an Adriatic and Dalmatian Coast cruise with a private Vatican tour, Colosseum arena entrance, and foodie market tour in Rome. Listen to the Venetian clock tower bells of Torre dell’Orologio strike the hour as hundreds of pigeons scatter about St. Mark’s Square. Sip crisp and dry Verdicchio paired with octopus salad or garlic-flavored black risotto in delicious Dubrovnik. Drift past the blue domes of Our Lady of the Rocks, a sanctuary for Kotor’s local fishermen for nearly 2,000 years. Sample succulent baked cardoon stalks harvested from Sicilian thistles and dusted with melted aged Parmesan cheese near the precipitous slopes of Mount Etna in Giardini Naxos. Experience an exclusive tour deep into the storied shadows of the Colosseum, sidestep crowds during a private tour of some sectors of the Vatican Museums and the Sistine Chapel, and dine in a Rome restaurant featuring authentic Italian dishes.

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.

The allure of the Adriatic beckons to both new and seasoned travelers for its unspoiled shorelines and panoramic vistas. While the views from Santorini’s turquoise-topped domes are among the most celebrated in the world, don’t linger long or you’ll miss sailing on a catamaran to the volcanic islands of Nea Kameni and Palea Kamini, or even hiking above the famous steaming, sulfurous volcanic vents. Graze on lightly toasted Monopoli bread topped with roasted peppers and tangy, tobacco-flavored sundried tomato paté, which pairs perfectly with Puglia’s full-bodied Salice Salentino DOC red wines. Soar skyward as a cable car carries you to the sweeping vistas high above the red, terracotta-topped buildings of Dubrovnik, Croatia. Discover the beauty and cultural heritage interwoven with Zadar’s ‘white gold’ Pag lace, then test your skills at lacemaking under the guidance of a skilled Croatian artisan. Walk along the Venetian-styled piazzas of Venice -- romantic settings for countless films -- or float along the narrow canals as you’re serenaded by a gondolier. Sample Montenegro organic olive oils at a family-run estate in the rural countryside outside the village of Tici. Your cruise eventually winds around and up the Italian western coastline to Rome, the former center of ancient Western Civilization. Wander between the arches and broken walls of the Colosseum, or walk among the dead in the narrow corridors in the Catacombs of Rome. Before considering airline connections or adventures on other continents, toss a coin from your right hand over your left shoulder into the Trevi Fountain, so that you’re guaranteed to revisit the charms of the Italian capital in your near future.

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.

Embark on your personal Homeric odyssey as you sail from Athens, cradle of Western Civilization, and explore the islands and shorelines throughout Greece, Asia Minor, Croatia and Italy. Board a small Mykonos boat and explore the remote temples and amphitheater on uninhabited Delos, a sacred place where ancient Greeks honored the mythical birthplace of Apollo and Artemis. Discover authentic preparation techniques for fried Greek meatballs and tart, creamy tzatziki under the guidance of a Rhodes taverna chef. Walk in the steps of ancient kings as you inspect the living quarters, storerooms and archaeological exhibits throughout the Palace of Knossos near Agios Nikolaos. Catch a Zadar sailboat bound for a 5th century fishing port on the island of Ošljak and pristine archipelago stops in the Adriatic Sea. This delicious and delightful journey concludes among the canals and piazzas of Venice, where you can experience the classic and timeless romance of being serenaded by your gondolier along the Noale or Grand Canals that connect over 100 tiny islets throughout the Venetian city.

Complimentary Destination Discovery Event • Kusadasi: Evening in Ephesus

Roam between the broken monoliths and columns in the Roman Forum, Western Civilization’s former epicenter. Gaze across Catania’s umber-hued, terracotta-tiled skyline to the steaming summit of Mount Etna as you sample authentic Sicilian dishes like densely textured handmade pasta topped with aromatic variations like sundried tomatoes, golden-brown dried grapes, fresh basil and minced garlic. This exquisite cruise around Italy’s Apennine Peninsula is abundant in opportunities to explore the lesser-known landmarks and narrow ancient streets of sleepy villages throughout the central Mediterranean. Sip citrus-sweet limoncello from frosty glasses while locals haggle over the proximities of their bocce balls on nearby gravel courts. Land at the tiny port of Lipari in the Aeolian Islands north of Sicily, and explore a Norman Castle built in medieval times, or master the art of Sicilian-style pizzas as you combine local ingredients into your own culinary creation. Step inside the cool and shady Romanesque splendor of Kotor Cathedral in Montenegro, or venture to the nearby pedestrian-only village of Perast and sample sweets recreated from Baroque-era recipes. Capture the Old World ambiance of Split’s Diocletian Palace in the right light during a hands-on photo tour with an award-winning international photojournalist. Your delightful journey concludes in Venice among romantic gondolas and exquisite Italian architecture, where you can reflect on your cruise memories as you float canals or search for last-minute souvenirs small, family-owned artisan shops featuring handcrafted glassware and ornamental metalwork.

Rich with evocative history, unique culture and distinct cuisine, today’s Iberian Peninsula is the result of a complex confluence of civilizations. Contrast this extraordinary region with the rest of Southern Europe during this 18-day cruise spanning nearly the length of the Mediterranean Sea. Admire Moorish architectural influences in the walled port of Cadiz as you compare bready and clear regional ‘fino’ sherries with sweet, ‘cream’ sherries. Soar skyward in a gondola to the scenic vista atop Gibraltar summit. Gaze up at the towering walls of the Alcazaba of Almería, a formidable Moorish fortress overlooking the tiny Andalucian port. Peruse the works of Gaudí, Dalí, and Picasso throughout Barcelona’s museums, galleries and exhibitions. Pair authentic Italian cuisine with lip-puckering Limoncello adjacent to a bustling piazza or quiet, cobblestoned Amalfi side street. Witness the power of geologic instability as you travel inland to explore Catania’s Castello Ursino, a Medieval-era castle initially built on Sicily’s coastline 800 years ago. Float across the mirrored surface of an underground lake in the Caves of Diros far below Gythion, Greece. This exceptional journey concludes in Athens among the shadows of the towering Acropolis, where you can raise a glass of anise-scented ouzo among the company of family and friends.

Barcelona to Athens - 20 Days

Discover magic moments unique to extended port stays during this 20-day cruise tracing the sundrenched coastlines and reclusive ports throughout Spain, Italy, Malta, Greece and Turkey. Wander along the long the curved walls of circular Bellver Castle outside Palma de Mallorca, or dine on tapas made from toasted bread topped with salty hams, capers, anchovies and more. Board a private Amalfi boat bound for the Moorish port of Positano, a remote haven for artists, artisans and discerning shoppers seeking one-of-a-kind stylish apparel and accessories. Wind your way through narrow, alabaster passages intertwining the outskirts of Mykonos before stopping for refreshing Greek beers at a late-night waterfront café. Step among broken statues in the former ancient port of Ephesus and dine by moonlight by the towering columns of the Celsus Library. Delve into the legendary labyrinth of the mythological Minotaur below the Minoan Palace of Knossos. Follow the aroma of fresh breads and local wines throughout the flagstone arterials of the tiny medieval village of Monemvasia. This remarkable extended odyssey ends in Athens, where you can revisit the Parthenon at the top of the Acropolis or seek out savory gyros, dolmades and keftethes among the dozens of eateries and cafés throughout the thriving capital.

Complimentary Destination Discovery Event • Kusadasi: Evening in Ephesus

Barcelona to Venice - 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. 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 Riviera.

From the moment you arrive in the 3000-year-old city of Athens, dive right into ancient history at the Acropolis Museum. The voyage begins with a stop in Nafplio—one of the most romantic cities in Greece. Climb 999 steps to the Palamidi Castle or visit the UNESCO site of Epidaurus, where people travel hundreds of miles to be healed. Iconic Mykonos is a charmer with whitewashed churches and thatch-roofed windmills and the mythical birthplace of Apollo is just a ferry ride away. A visit to Kusadasi, Turkey means a chance to see Ephesus—one of the greatest outdoor museums in the world. The wonders continue with the sacred isle of Patmos where St. John wrote the Book of Revelation. Breathe in the beauty of Santorini with spectacular cliffs rising from the deep azure sea and visit Bronze Age excavations at the UNESCO site of Akrotiri. Monemvasia boasts churches dating to the 12th century and Milos teases the palate with delicious fresh seafood and sparkling white sands sans crowds. Cruise the dramatic Corinth Canal, only accessible to other private yachts and Greek mail steamers. Visit the historic site of Delphi where the Oracles were read and Delphi Archaeological Museum featuring the country’s finest works of art. Explore the beautiful beaches of Fiskardo and step back into the Crusader days in the walled city of Valletta, Malta. Cruise on to Sicily’s charming village of Giardini Naxos nestled in one of the world’s most beautiful bays and take your pick of UNESCO World Heritage Sites from Sorrento, including the archaeological areas of Pompeii and Torre Annunziata, or the 4th century B.C. city of Herculaneum. Ponza provides a welcome respite to relax with locals in this laid back one street island town before arriving in the metropolis of Rome to visit the Vatican, St. Peter’s Square, the Trevi Fountain, the Roman Forum and a host of other ancient relics.

Uncover the distinct and authentic culinary advantages of pairing specific olive oils with various Italian dishes under the guidance of the Maître d’hotel inside Portofino’s landmark Splendido Hotel. Roll the dice in a Monte Carlo casino or stroll along the narrow streets and tight corners on one of the most famous race courses on the Formula One circuit. Seek out the charming medieval village of Bormes Les Mimosas or the narrow cobbled streets of Old Town Antibes. Glide past walled gardens and centuries-old orange groves as you take a precipitous driving tour along the winding Golden Corniche through the French Riviera. Meander between the high columns and dust-covered scaffoldings of the Sagrada Família Cathedral in Barcelona, the largest unfinished Roman Catholic Church in the world. Or set out for tapas and riojas hours after sunset, when the aromas and din from lively bars and cafes intensify with the arrival of epicurean pleasure-seekers. There, among the ceaseless trilingual convergence of English, Spanish and Catalonian, you’ll find no better place to raise a glass to the satisfying indulgences on this Mediterranean adventure.

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.

From the grandeur of ancient Rome to the Renaissance splendors of the Western Civilization’s greatest artists, few countries have influenced the modern world like Italy. This 11-day cruise tour visits both sides of the Italian peninsula with stops in romantic Venice, small ports along the scenic Dalmatian coast, and a delicious and captivating land tour of both Tuscany and Rome. Float along Venetian canals while listening to singing gondoliers. Soar to expansive Adriatic views as a tram sweeps you high above Dubrovnik’s ancient walls and rustic old town charms. Slurp rich Spaghetti alle Vongole, blended with fresh clams, rich shrimp or fried calamari at a table overlooking the Sorrento seashore. Walk around the towering white marble statue of Michelangelo’s David, a Renaissance masterpiece embraced by Florentines as a symbol in defense of civil liberties. Sniff and sip the red, black and sour cherry aromas and flavors characteristic of the best Chianti wines. Wander Roman piazzas, ancient gathering spaces for families and neighbors for over 2,000 years.

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