Sicilian Splendors
 
Rome to Rome
Thu May 28, 2026 - Sun Jun 7, 2026,
 10 days
 on Wind Surf
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Starting from $4,499 USD
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Rome to Rome
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.
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: 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 5: 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 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.
Popular Highlights
amphitheater
Stand in the massive Greek amphitheater in Syracuse, a city with 2,700 years of history.
Erice
From Trapani travel to the medieval town of Erice and admire the Castle of Venus and the 700-year-old Mother Church.
Pompeii
Walk the silent streets of Pompeii in the shadow of Mount Vesuvius.
St Peters Basilica
Watch sunbeams from Michelangelo’s dome play on the walls of St. Peter’s Basilica in Rome.
Valleta
Relive the Middle Ages as you view the historic tapestries and armor in Valletta’s Palace of  the Grand Masters.
Valley of The Temples
Take in some of the world's best-preserved Greek ruins at the Valley of the Temples.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Thu May 28
Rome
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Fri May 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat May 30
Syracuse, Italy
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun May 31
Gozo
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jun 1
Valletta
Arrive:  12:01 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Jun 2
Porto Empedocle
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Wed Jun 3
Trapani
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Thu Jun 4
Lipari
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Fri Jun 5
Sorrento
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Sat Jun 6
Amalfi
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Jun 7
Rome
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
“As you approach Agrigento and the legendary Valley of the Temples, you’ll feel as though you’ve stepped into an Italian painting. Surrounded by architectural treasures, you’ll experience one of the most important archaeological sites in the world, where impressive edifices from 510 to 430 B.C. evoke a haunting and romantic history.”
The Story
Placed like a stepping-stone between the boot of Italy and the tip of Tunisia, Sicily has been in a cultural tug of war for centuries. Its location at the crossroads of the Mediterranean has attracted merchants, invaders, and immigrants. First the Phoenicians, Greeks, and Romans. Then Byzantines, Arabs, and Vikings. Finally, Normans, Germans, and Spaniards. In the process, these diverse cultures have seasoned everything from the island’s language to its cuisine. Part European, part African, it’s still Italy, only with cacti and palm trees, souk-like markets, couscous and saffron.
 
The fertile volcanic soil supports hillside groves of olives, almonds, pistachios, oranges, and lemons. Historic ruins are everywhere. And encircling it all are over 280 beaches, from stunning black to velvety white to Lipari’s silvery-gray. But of all the attractions you’ll find here (and there are many), one of the best is Sicily’s authenticity. The island is what Italy used to be, and as we visit smaller ports like Xlendi and Porto Empedocle and get to know the people, you’ll find it hard to pick a favorite.
Insider Tips:
  • Street food is very popular in Sicily and it can give you a real taste of the island’s multicultural background. The cuisine is different than mainland Italy’s, and blends both European and African influences. Rice balls, eggplant, pasta, fava beans—the flavors are varied and delicious.
  • Sicily has some of the best ancient Greek ruins outside of Greece, from temples to theaters where the acoustics still astound scientists today. Some of the best are at the Valley of the Temples at Agrigento, and the theaters in Taormina and Ancient Syracuse.
  • Most businesses in Sicily take a siesta in the afternoon, often lasting from 1:00 until 4 or 5. Plan ahead if you plan to do any shopping.
  • Sicily is not flat, in fact it’s 85 percent hills and mountains. There are also lots of stairs and uneven cobblestones. So bring your best walking shoes if you’re going to explore on foot.
If you’re looking for an off the beaten path day trip from Catania, consider the baroque towns of the Val di Noto. These UNESCO World Heritage Sites in the Noto Valley were all rebuilt in a unique late Baroque style after an earthquake in 1693.
Wind Surf
On any day, our 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area – and, appropriately, that’s only the beginning.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
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 $4,499 per guest
? All-inclusive price from $5,489 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.
? Cruise only from $4,899 per guest
? All-inclusive price from $5,889 per guest
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.
? Cruise only from $5,199 per guest
? All-inclusive price from $6,189 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 $5,649 per guest
? All-inclusive price from $6,639 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 $5,899 per guest
? All-inclusive price from $6,889 per guest
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.
? Cruise only from $8,099 per guest
? All-inclusive price from $9,089 per guest
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.
? Cruise only from $8,399 per guest
? All-inclusive price from $9,389 per guest
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
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Tue, May 27 - Fri, Jun 6, 2025
WIND SURF
$8,739
$7,749
Thu, Jul 10 - Sun, Jul 20, 2025
WIND SURF
$6,189
$5,199
Mon, Sep 22 - Fri, Oct 3, 2025
WIND SURF
$8,188
$7,099
Thu, May 28 - Sun, Jun 7, 2026
WIND SURF
$5,489
$4,499
THIS
SAILING
Sun, Sep 27 - Wed, Oct 7, 2026
WIND SURF
$5,389
$4,399