Sicilian Splendors
 
Rome to Rome
Tue May 27, 2025 - Fri Jun 6, 2025,
 10 days
 on Wind Surf
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Starting from $4,548 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
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.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Tue May 27
Rome
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Wed May 28
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu May 29
Syracuse, Italy
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Fri May 30
Valletta
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Sat May 31
Gozo
Arrive:  7:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Jun 1
Porto Empedocle
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Jun 2
Trapani
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Jun 3
Lipari
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Wed Jun 4
Sorrento
Arrive:  8:00 AM
Depart:  11:59 PM
Watersports Platform: 
Thu Jun 5
Amalfi
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Fri Jun 6
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.
Accommodations & Pricing
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar)
Guaranteed Cabin** (chosen by Windstar) 
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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
ALL DATES &
FARES
7-for-7
Last Minute Cruise Deals
Pick Your Perk
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
Tue, May 27 - Fri, Jun 6, 2025
WIND SURF
$5,538
$4,548
THIS
SAILING
Thu, Jul 10 - Sun, Jul 20, 2025
WIND SURF
$4,828
$3,838
Mon, Sep 22 - Fri, Oct 3, 2025
WIND SURF
$8,188
$7,099
Thu, May 21 - Sun, May 31, 2026
WIND SURF
$5,689
$4,699
Sun, Sep 27 - Wed, Oct 7, 2026
WIND SURF
$6,089
$5,099