Historic Harbors of Italy & Beyond

From $6,745 per person

14 days

Ship: Wind Surf

Historic Harbors of Italy & Beyond

Journey Summary

  • Day 1 - May. 21, 2026, Thu. - Rome
  • Day 2 - May. 22, 2026, Fri. -
  • Day 3 - May. 23, 2026, Sat. - Syracuse, Italy
  • Day 4 - May. 24, 2026, Sun. - Valletta
  • Day 5 - May. 25, 2026, Mon. - Gozo
  • Day 6 - May. 26, 2026, Tue. - Porto Empedocle
  • Day 7 - May. 27, 2026, Wed. - Trapani
  • Day 8 - May. 28, 2026, Thu. - Lipari
  • Day 9 - May. 29, 2026, Fri. - Sorrento
  • Day 10 - May. 30, 2026, Sat. - Amalfi
  • Day 11 - May. 31, 2026, Sun. - Rome
  • Day 12 - Jun. 1, 2026, Mon. - Portovenere
  • Day 13 - Jun. 2, 2026, Tue. - Bonifacio, France
  • Day 14 - Jun. 3, 2026, Wed. - Rome

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - May 21, 2026

Rome

In this enchanting city the past and present intersect in perfect harmony. Casually intermingled among ancient ruins and majestic cathedrals are the trappings of a modern metropolis: Skyscrapers,cafes, boutiques selling designer footwear. But of course what you seek first in the heart of Rome is its breathtaking history.  A good place to begin is the Vatican, with its Sistine Chapel and St. Peter’s Basilica. Works by Bernini, Michelangelo, Caravaggio, and Raphael are just a few of those on display, any one of which is worth hours of contemplation. Then the ancient ruins—Colosseum, Forum, Circus Maximus. And of course the Trevi Fountain for the obligatory coins promising your return to the Eternal City.

Day 2 - May 22, 2026

Day 3 - May 23, 2026

Syracuse, Italy

Rich in both Greek and Roman history and home of the mathematician Archimedes, Syracuse is full of ancient ruins including the Roman Amphitheater, Teatro Greco, and the Orecchio di Dionisio. The Ortigia, or Old Town is full of sites to see like the Ortigia Cathedral which houses a number of relics of St. Lucy, the patron saint of Syracuse.
 
 

Day 4 - May 24, 2026

Valletta

Malta’s capital city, a UNESCO World Heritage Site, is among the world’s smallest, yet definitely most charming.  Graced with the paintings of Caravaggio and kissed by beautiful shorelines, you’ll find photographic icons at almost every turn.  Not to be missed is a visit to the stately Palazzo Parisio to glimpse the enchanting lifestyle of Malta’s nobility. 

Day 5 - May 25, 2026

Gozo

Pretty Xlendi Bay lies on the west coast of Gozo, an island long thought to be the mythical Ogygia of Homer’s Odyssey. In the story, Calypso fell in love with Odysseus and held him captive for seven years.. The reputed Calypso Cave is just one of several intriguing caves on the island. There’s also Caroline’s Cave, a natural grotto that was once a private swimming hole for nuns. Surprisingly for such a small island, Gozo is home to the oldest freestanding temples in the world, the Ggantija Temples, nestled among the rolling green hills. You should also visit the Citadella, a small, fortified town that houses the island’s Cathedral, the Museum of Archaeology, the Folklore Museum, and the Old Prisons.

Day 6 - May 26, 2026

Porto Empedocle

Here you’ll find what are widely acclaimed as the best, ancient ruins in the entire Mediterranean. Imagine the wonders of Athens, of Ephesus, of legendary Olympia itself. Then imagine them all in one place, at Agrigento, a UNESCO World Heritage Site. As you wander the verdant ridge overlooking the Mediterranean you will be transported to the 5th and 6th centuries. The irresistible scent of olive, almond, and eucalyptus trees will entice you back to the present. This is one of the world’s most beautiful sites. 

Day 7 - May 27, 2026

Trapani

At once ancient and contemporary, Trapani is a city of contrasts. From the salt marshes that produce much of the Mediterranean’s signature colored salts, to the intricate mosaics of Mozia and the famous wines of Marsala, to the best view in all of Sicily from the medieval hill town of Erice where the colorful gardens are rivaled only by the cannolis for pure sensory delight. The line of 17th century windmills, still hard at work in ancient Phoenician salt marshes beckons you to return to Trapani again and again. 

Day 8 - May 28, 2026

Lipari

Take time on shore to explore the beautiful village and enjoy the exclusive access that only a small ship can provide in a port large cruise ships cannot reach.   An optional tour will introduce you to the highlights of the largest of the seven Aeolian Islands, well-known for its mythological connections and a UNESCO World Heritage Site. 

Day 9 - May 29, 2026

Sorrento

UNESCO World Heritage Sites abound in Sorrento.   Optional tours will take you to the archaeological areas of Pompeii and Torre Annunziata, or the 4th century B.C. city of Herculaneum. Perhaps your choice will be a boat ride to Positano, the legendary home of the Sirens. Perched on a terrace on the spectacular Amalfi Coast, Sorrento offers exceptional views of the Bay of Naples and Mount Vesuvius. 

Day 10 - May 30, 2026

Amalfi

The town of Amalfi lies at the mouth of a deep ravine surrounded by dramatic cliffs and coastal scenery. As part of the Amalfi Coast, it has been designated a UNESCO World Heritage Site and is an important tourist destination. The whole region is famed for its lemons, which are about double the size of other lemons, and the production of the limoncello liqueur. An optional tour can take you to the UNESCO archaeological areas of Pompeii, Positano and Ravello.

Day 11 - May 31, 2026

Rome

In this enchanting city the past and present intersect in perfect harmony. Casually intermingled among ancient ruins and majestic cathedrals are the trappings of a modern metropolis: Skyscrapers,cafes, boutiques selling designer footwear. But of course what you seek first in the heart of Rome is its breathtaking history.  A good place to begin is the Vatican, with its Sistine Chapel and St. Peter’s Basilica. Works by Bernini, Michelangelo, Caravaggio, and Raphael are just a few of those on display, any one of which is worth hours of contemplation. Then the ancient ruins—Colosseum, Forum, Circus Maximus. And of course the Trevi Fountain for the obligatory coins promising your return to the Eternal City.

Day 12 - June 01, 2026

Portovenere

Stunning UNESCO World Heritage Sites beckon you. Select an optional excursion to Pisa, known for its bell tower with its unintended tilt.  Tour the beautiful city of Florence, or the historic San Gimegnano. Or step back into Tuscany’s rustic tradition to visit the charming villages of Cinque Terre (Five Lands) by boat. 

Day 13 - June 02, 2026

Bonifacio, France

Bonifacio, located on the southern tip of Corsica, is renowned for its dramatic limestone cliffs and medieval citadel. The town's ancient fortifications and narrow, cobbled streets offer a glimpse into its rich history. Bonifacio's picturesque marina is filled with colorful yachts and cafes, providing stunning views of the Mediterranean. Notable sites include the King of Aragon's Staircase, carved into the cliffside, the Old Town, and Sartene, an ancient hillside community dating back to the 16th century.

Day 14 - June 03, 2026

Rome

In this enchanting city the past and present intersect in perfect harmony. Casually intermingled among ancient ruins and majestic cathedrals are the trappings of a modern metropolis: Skyscrapers,cafes, boutiques selling designer footwear. But of course what you seek first in the heart of Rome is its breathtaking history.  A good place to begin is the Vatican, with its Sistine Chapel and St. Peter’s Basilica. Works by Bernini, Michelangelo, Caravaggio, and Raphael are just a few of those on display, any one of which is worth hours of contemplation. Then the ancient ruins—Colosseum, Forum, Circus Maximus. And of course the Trevi Fountain for the obligatory coins promising your return to the Eternal City.

Dates and Prices

(per person*)

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* Per double occupancy. Some pricing may reflect single traveler rate.

Ship

Your cruise ship

The Wind Surf sailing through clear blue waters, showcasing its iconic tall sails against a bright sky.
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About this ship

Wind Surf

Wind Surf is the crown jewel of Windstar’s fleet—a majestic five-masted sailing yacht that delivers the romance of classic seafaring paired with the elegance and comfort of a modern small ship. As the largest vessel in Windstar’s collection, Wind Surf carries just 342 guests, preserving the line’s commitment to intimacy while offering generous space, upscale amenities, and a truly immersive style of travel.

Originally built in 1990 and acquired by Windstar in 1998, Wind Surf has undergone a series of thoughtful refurbishments that honor her graceful nautical lines while updating the interiors and onboard offerings to reflect a contemporary, boutique-luxury standard. Her soaring sails—automated yet fully functional—allow guests to experience the beauty of wind-powered cruising, often sailing into port with a sense of drama and authenticity no larger ship can replicate.

The ship features 154 ocean-view accommodations, including 31 suites and two deluxe Bridge Suites. Each stateroom is designed with timeless materials and a calm, coastal-inspired aesthetic. Marble bathrooms, L’Occitane amenities, premium linens, and well-appointed sitting areas provide comfort and functionality, while the larger suites offer expanded living space and additional privileges, including preferred dining reservations and personalized service.

Dining aboard Wind Surf is a sophisticated yet unpretentious affair, with multiple restaurants that celebrate culinary variety and regional inspiration. Amphora, the main dining venue, offers a nightly menu of gourmet dishes in an elegant, open-seating setting. Stella Bistro showcases refined French cuisine with modern flair, while Candles transforms the deck into a romantic, open-air grill under the stars. The Veranda is a casual breakfast and lunch spot overlooking the sea, and the Yacht Club Café offers light bites, specialty coffees, and ocean views throughout the day.

The onboard experience is as much about rejuvenation as it is exploration. Guests can unwind in the full-service World Spa by Windstar, exercise in the fitness center, or enjoy a swim in the pool followed by a soak in one of several hot tubs. A signature feature of the yacht is its watersports platform, which opens directly onto the sea and provides complimentary access to paddle boards, kayaks, snorkel gear, and more when anchored in select locations.

Wind Surf sails to some of the world’s most enchanting coastal regions, including the Mediterranean, the Caribbean, and Northern Europe. Her size allows her to slip into smaller ports and scenic harbors inaccessible to larger cruise ships, enabling more meaningful encounters with local culture, history, and natural beauty.

Elegant yet relaxed, polished but never pretentious, Wind Surf is designed for travelers who appreciate the thrill of the open sail, the comfort of spacious suites, and the rewards of authentic, unhurried discovery. She is not just a ship, but a sailing experience reimagined for the modern world.

Deckplans

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