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.

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 - 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.

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.

Venice to Athens - 9 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.

Rome to Barcelona - 10 Days

Leave the mundane behind as you cruise effortlessly from port to sparkling port along the world’s most fabled coastline. These are the places dreams are made of. The ultimate glamour of Marseille and Monte Carlo – the enchanting harbors of Portofino, Portovenere, and Portoferraio – and, of course, the world-class charms of Rome and Barcelona. Your voyage also takes you to places few cruise ships follow, like lovely San Remo on the Riviera of Flowers, the miniature continent of Corsica, and the quaint Provençal fishing village of Sanary-sur-Mer.

Sail into the summer season with a Mediterranean cruise that visits Greek and Adriatic coastlines before exploring the breathtaking and storied shores of Sicily and Italy during this 16-day adventure. Shortly after departing Athens transit the Corinth Canal, an impossibly narrow time-saving waterway that bypasses 400 miles of coastline, and is only accessible to small ships, so you enjoy the sights and splendors of the Temple of Apollo in Delphi the next day. Wander among Split’s thousand-year-old walls as you make your way to Diocletian’s Palace. Dine on tart and refreshing lemon gelato within sight of gondolas gliding beneath Venice’s Rialto Bridge. Your journey concludes near Rome, the epicenter of the Roman Empire and a contemporary focal point for Italian food and fashions. Sidestep growling scooter traffic as you make your way deep into Roman Forum ruins, take a seat in the Colosseum and don’t forget to ensure a return trip by tossing coins tossed into the lavish Trevi Fountain.

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.

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

Embark on a most exhaustive exploration of Greece, including 12 Grecian ports and an impressive transit of the Corinth Canal. Explore Italy and Turkey along the way. Examine the mysterious Grotte di Pilato on the island of Ponza, watery cavern openings that may have been used to hold moray eels destined for Europe’s earliest seafood dishes. Sample buffalo mozzarella paired with bread, olives and rich, regional Sangiovese red wines or bright and tart, white wines. Savor delicious Turkish cuisine among the pillars of the Celsus Library in Ephesus, formerly one of the largest libraries in the ancient world, and then linger for an evening concert among the ruins. Delve into the facts and fables surrounding the Colossus of Rhodes, a Greek harbor monument rivaling the Statue of Liberty’s height. Reflect on flavors savored and memories made as you wander among scarred blocks atop the Acropolis in Athens, or sip anise-flavored liquors among locals at a small café.

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.

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.

Few Mediterranean cruises offer the unique combination of romance and racing like this Star Collector adventure from the canals of Venice to the 2020 Monaco Grand Prix in Monte Carlo. Along the way you’ll explore the art, architecture, and cultural customs and cuisines throughout Italy, Croatia, Monetengro, and France. Taste local wines paired with homemade cheese in an intimate Croatian family wine cellar outside of Rovinj. Kayak together on Kotor Bay in Montenegro. Glide inside the glowing azure chambers of the fabled Blue Grotto near Giardini Naxos. Sip sweet limoncello liqueur together at a sidewalk café in Sorrento. Witness Saturday qualifying for the 2020 Monaco Grand Prix prior to an exclusive tour of the storied pits. After evening festivities and an overnight stay in Monte Carlo, you’ll enjoy sweeping views of the track on race day, along with a gift package that includes ear plugs, high-definition binoculars and seat cushion.

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

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. 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.

Venice to Barcelona - 15 Days

Take advantage of the Mediterranean’s milder temperatures and uncrowded museums and markets during this 15-day autumn cruise. Set sail from Venice, not far from the storied Grand Canal and the linen-covered tables and fragrant pink peach Bellini cocktails at historic Harry’s Bar. Take in the view of Rovinj from the Baroque-styled heights of St. Euphemia’s alabaster-hued tower. Reflect on magnificent oil paintings and the tradition of throwing stones into the sea inside the Church of Our Lady of the Rocks across the scenic bay from Kotor, Montenegro. Dine on Coda alla Vaccinara, or sauce-covered oxtail, a favorite local dish in Rome. Shop stylish one-of-a-kind French beachside boutiques in Nice. Ride a gondola to Mont Faron’s scenic summit, high above Toulon. This memorable Mediterranean cruise culminates among the artistic urban splendors of Barcelona, where you can browse kiosks, shops, and cafés along La Ramblas, and tour Sagrada Família, Antoni Gaudi’s artistic vision of a contemporary Roman Catholic basilica.

Venice to Lisbon - 23 Days

Oohs and ahhs over the sublime scenery alternate with oohs and ahhs over magnificent manmade creations on this voyage along the Dalmatian Coast, Ligurian Riviera, Côte d’Azur, and Costa del Sol. This is a stretch where Blue Flag beaches have to jostle for elbow space and castles, palaces and cathedrals take every form known to man – and then some. This is where the imaginations of Cezanne, Monet, Matisse, Picasso, Dali, and Gaudí were ignited. Here is where great romances blossomed: Richard Burton and Elizabeth Taylor in Portofino, Princess Grace and Prince Rainier in Monte Carlo, Romeo and Juliet near Venice. Sail through waters where the legendary sirens are said to live, watch fearless castellers climb human pyramids, play a game of picign with gregarious Croatians. Our small ships take you to smaller and less-visited ports like Sanary-sur-Mer and Portoferraio, and get you closer to town than the big ships can get in places like Dubrovnik, Venice, Barcelona, and Málaga. What you do with the extra time is entirely up to you.

Combine the Riviera’s romantic, Old World ambiance with the grandeur of the Roman and Greek empires during this 17-day cruise featuring stops in Spain, France, Monaco, Italy, Malta, and Greece. Sail north from thriving Barcelona to the quiet fishing village of Palamos, where white sand beaches almost rival the delicious local prawns. Relax over French press coffee and freshly baked butter croissants at an outdoor beachside café in romantic Sanary-sur-Mer, then sample deep red Bandol wines in a wine bar. Test your luck among the gilded opulence of a Monte Carlo casino. Stroll among the blocks, columns arches and former temples throughout the Roman Forum as the Colosseum looms in the distance. Wander Valletta’s narrow passages and scarred Maltese fortifications. Your remarkable journey ends near Athens, home of the Parthenon and the epicenter of Western Civilization’s Classical Period, where the ideas of European art, literature and philosophy took root among early scholars thousands of years ago.

Arrive rested, refreshed and ready to explore the Iberian Peninsula during this 21-day transatlantic cruise combined with port stops in the Azores, Portugal,and Spain. Slip past the sloped, imposing walls of Castillo San Cristóbal on your way across the Atlantic. Relax and book spa appointments or reconnect with friends and family as you gradually acclimatize to time zones and arrive ready to explore Horta on the island of Faial among the Azores Archipelago. Explore the waterfront of Portimao, a small Portuguese fishing port with a thriving sardine industry. Indulge in the visual contrasts of Almería’s 500-year-old Gothic cathedral and the modern Neolithic exhibits housed inside the angular and contemporary Museum of Almería. Your transatlantic vacation concludes along Barcelona’s vibrant waterfront, where you can sample rich seafood paella paired with touristy sangrias, and dark, smoky red Tempranillo wines.

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.

Thank You!

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

Click here to view our current special offers.

ok