Historic Harbors of Italy & Beyond

 
Rome to Rome
Thu May 21, 2026 - Wed Jun 3, 2026,
 13 days
 on Wind Surf
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Starting from $6,999 USD
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Rome to Rome
Fall in love with sailing again on the elegant Wind Surf. This 13-night sailing visits Italian seaside villages, smoldering Sicilian volcanoes, and imposing Malta monuments. Wander between shady palms and quarried caves at the Neapolis Archaeological Park--an UNESCO World Heritage Site where ancient actors orated, artisans wove ropes, and tyrants eavesdropped on prisoners. Roll offroad on mountain bikes to a scenic Maltese village beyond the high-walled port of Valleta, Malta. Meander between Pompeii's Roman baths, markets, and temples beneath brooding Mount Vesuvius. Stroll from the Spanish Steps to the Trevi Fountain to the fabled Pantheon during a walking tour of cosmopolitan Rome. Board a Portovenere boat bound for Cinque Terre's picturesque terraces and sample fresh mussels paired with local wines in the colorful village of Vernazza.
voyage map
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Day 1: 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.
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Day 3: 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.
 
 
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Day 4: 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. 
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Day 5: 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.
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Day 6: 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. 
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Day 7: 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. 
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Day 8: 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. 
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Day 9: 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. 
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Day 10: 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.
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Day 11: 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.
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Day 12: 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. 
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Day 13: 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.
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Day 14: 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.
Popular Highlights
Bonifacio
Wander the cobblestone streets of Bonifacio, Corsica’s medieval clifftop fortress, offering panoramic views of the sea and limestone cliffs.
Gozo
While in Gozo, visit the serene Ta’ Pinu Basilica, a striking neo-Romanesque church and important pilgrimage site surrounded by tranquil countryside.
Portovenere
From Portovenere, boat along the Cinque Terre’s picturesque coastline.
Rome
With three days in Rome, you’ll have time to see it all – from the Sistine Chapel and the Spanish Steps to the iconic Colosseum.
Syracuse
You’ll want to visit the caves of Syracuse to walk through centuries of history—once used as quarries, hiding places, and storied backdrops of Greek legends.
Trapani
Visit Trapani to witness its shimmering salt pans, where sea salt has been harvested for centuries using traditional methods that turn nature into flavor.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Thu May 21
Rome
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Fri May 22
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat May 23
Syracuse, Italy
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun May 24
Valletta
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Mon May 25
Gozo
Arrive:  7:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue May 26
Porto Empedocle
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed May 27
Trapani
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Thu May 28
Lipari
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Fri May 29
Sorrento
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Sat May 30
Amalfi
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun May 31
Rome
Arrive:  7:00 AM
Depart:  4:00 PM
Watersports Platform: 
Mon Jun 1
Portovenere
Arrive:  9:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Jun 2
Bonifacio, France
Arrive:  10:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Jun 3
Rome
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Category A
Category A
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Call for Availability
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
? Call for Availability
Category B
Category B
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $6,999 per guest
? All-inclusive price from $6,999 per guest
Category AX Deluxe
Category AX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $8,199 per guest
? All-inclusive price from $8,199 per guest
Category TX Deluxe
Category TX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Cruise only from $8,519 per guest
? All-inclusive price from $8,519 per guest
Category BX Deluxe
Category BX Deluxe
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.
? Call for Availability
Suite
Suite
With 376 square feet, you’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.
? Call for Availability
Officer's Suite
Officer's Suite
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where our own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.
? Call for Availability
Bridge Suite
Bridge Suite
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.
? Call for Availability
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Marina
*Select voyages
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Thankful For Travel Sales Event
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Thu, May 21 - Wed, Jun 3, 2026
WIND SURF
$6,999
$6,999
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SAILING