Italy - Windstar Cruises

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Small Ship 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.

Windstar Knows the Way to Italy

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.

La Bella Vita Our Italy cruises take you to “must see” destinations like the Vatican and to uncrowded ports you may not know, but will fall in love with once you visit. And with long days in port and itineraries from 7 to 23 days, you’ll have time to savor it all.

Italy Beyond Ordinary - Smaller Ports Come with us to places off the big-ship radar and discover the world they pass by. Explore the Riviera favored by yachtsmen, still brimming with glamour and charm.Visit smaller ports off the beaten path—Gozo and Amalfi with their emerald grottos, Lipari with its authentic Sicilian pizza, and the quiet piazzas of Porto Empedocle.

More Time, More Exploration - Overnights Our port-rich itineraries take you to a number of diverse and interesting towns, but they also give you time to explore and learn what makes each one special. Overnights in Rome and Monte Carlo let you bring home unforgettable memories of the Sistine Chapel or watching the Monaco Grand Prix, while late night departures let you visit attractions further inland from Sorrento, sample the local cuisine and night life in Kotor and Cadiz, or enjoy the spectacle of ancient towns like Valletta and Dubrovnik lit up at night.

Best of the Land and Sea - Cruise Tours Available Our Cruise Tours combine highlights along the coast with a few days of exploring destinations further inland to give you the best of both ship and shore. Check off more of your bucket list items and let Windstar handle all the arrangements, from accommodations and transfers to guides and attraction admission. A scenic cruise on Lake Como, St. Mark’s Square, the Colosseum, the Vatican Museum… so many delights and all so convenient.

Featured Port: Giardini Naxos (Taormina), Sicily, Italy Giardini Naxos was Sicily’s oldest Greek city, and in its day, it outshined nearby Taormina. Both live in the shadow of Mount Etna, a capricious neighbor who is prone to violent eruptions but also blesses the area with fertile soil. In the first century Pliny the Elder praised Taormina’s wines, grown from grapes nourished by Mount Etna. Try some yourself as you peruse the irresistible beaches, medieval buildings, and an ancient Greek theater that’s still used for performances.

Shore Excursion Must-Do: Concierge Collection: Camogli Highlights & Punta Chiappa (Portofino, Italy) San Rocco is a small hamlet, settled on the top of Portofino’s National Natural Park and is the starting point of a lovely path. The walk follows the coast line and stops in front of the little church of San Nicolò Capodimonte for a short visit. Proceed then to Punta Chiappa, a rocky formation jutting out into the sea, which is also a very interesting area due to a breathtaking landscape and this site can be reached only by path or boat, no roads, no vehicles! All around there is the coastline of Liguria, ahead Corsica, and behind on land there is the Batteria di Punta Chiappa hidden in the mountains.

Only Windstar Brings You Close Enough

The World's Best Small Ship Cruise Line

A Piece of Greece, a Slice of Sicily & the Corinth Canal

Date and Duration
10th May 2026 (8 Nights)

Port to Port
Athens to Barcelona

Ship
Star Legend

Fares from

£2,413_pp

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Adriatic Icons & Venetian Treasures

Date and Duration
15th July 2026 (9 Nights)

Port to Port
Venice to Venice

Ship
Wind Surf

Fares from

£2,100_pp

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Adriatic Icons & Venetian Treasures

Date and Duration
9th August 2026 (9 Nights)

Port to Port
Venice to Venice

Ship
Wind Surf

Fares from

£2,050_pp

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Star Collector: Mediterranean Masterpieces of Italy & Northern Greece

Date and Duration
20th August 2026 (14 Nights)

Port to Port
Rome to Athens

Ship
Wind Spirit

Fares from

£3,392_pp

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Adriatic Icons & Venetian Treasures

Date and Duration
10th September 2026 (9 Nights)

Port to Port
Venice to Venice

Ship
Wind Surf

Fares from

£3,407_pp

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Star Collector: Mediterranean Masterpieces of Italy & Northern Greece

Date and Duration
19th September 2026 (14 Nights)

Port to Port
Rome to Athens

Ship
Star Legend

Fares from

£4,740_pp

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