Sicilian Splendors

 
Rome to Rome
Mon Jul 5, 2027 - Thu Jul 15, 2027,
 10 days
 on Star Legend
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Starting from $3,699 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 2: Cruising Stromboli, Italy
Weather conditions depending, you will see the volcano that never sleeps as you cruise by Stromboli and with any luck observe the active lava stream by day or the glowing lava at night.
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Day 3: 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 4: Palermo, Italy
Palermo, the vibrant capital of Sicily, is a city where history, culture, and flavor come alive. Known for its stunning mix of Arab-Norman architecture, bustling markets, and rich culinary traditions, it offers a unique blend of Mediterranean charm and timeless heritage. From ornate cathedrals and grand theaters to lively piazzas and street food stalls, Palermo is a feast for the senses and a true gateway to Sicily’s soul.
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Day 5: 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 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: 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 8: 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 9: Giardini Naxos
Today you’ll discover one of Sicily’s jewels, the charming village of Giardini Naxos, nestled in one of the world’s most beautiful bays. An optional excursion to the popular hillside town of Taormina will be a highlight of your voyage — from the stunning setting of the iconic Greek Theater to the sparkling beaches along the Ionian Sea. Take a more adventurous tack and explore the UNESCO site of Mount Etna, Europe’s most active volcano.
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Day 9: Transit Straits of Messina
The Straits of Messina, a narrow passage between Sicily and mainland Italy, are famed for their dramatic scenery, strong currents, and mythological legends. Linking the Tyrrhenian and Ionian Seas, this strategic waterway has long been a crossroads of history and culture. As you sail through, you’ll be treated to views of rugged coastlines, picturesque villages, and possibly even the whirlpools that inspired the ancient tales of Scylla and Charybdis.
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Day 10: 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 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
MarinaWatersports Platform: 
Mon Jul 5
Rome
Arrive:  
Depart:  4:00 PM
Watersports Platform: 
Tue Jul 6
Cruising Stromboli, Italy
Arrive:  4:00 PM
Depart:  11:00 PM
Watersports Platform: 
Wed Jul 7
Lipari
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Jul 8
Palermo, Italy
Arrive:  8:00 AM
Depart:  11:00 PM
Watersports Platform: 
Fri Jul 9
Trapani
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Jul 10
Porto Empedocle
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Jul 11
Valletta
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Jul 12
Syracuse, Italy
Arrive:  8:00 AM
Depart:  11:00 PM
Watersports Platform: 
Tue Jul 13
Giardini Naxos
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Tue Jul 13
Transit Straits of Messina
Arrive:  7:00 PM
Depart:  8:00 PM
Watersports Platform: 
Wed Jul 14
Sorrento
Arrive:  8:30 AM
Depart:  3:00 PM
Watersports Platform: 
Thu Jul 15
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 Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? Cruise only from $3,699 per guest
? All-inclusive price from $4,689 per guest
Ocean View Suite
Ocean View Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
? Cruise only from $4,049 per guest
? All-inclusive price from $5,039 per guest
Ocean View Suite 1
Ocean View Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $4,149 per guest
? All-inclusive price from $5,139 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $4,279 per guest
? All-inclusive price from $5,269 per guest
Ocean View Suite 2
Ocean View Suite 2
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $4,359 per guest
? All-inclusive price from $5,349 per guest
Ocean View Suite 3
Ocean View Suite 3
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $4,449 per guest
? All-inclusive price from $5,439 per guest
Balcony Suite
Balcony Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $5,639 per guest
? All-inclusive price from $6,629 per guest
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $5,779 per guest
? All-inclusive price from $6,769 per guest
Balcony Suite 1
Balcony Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $6,019 per guest
? All-inclusive price from $7,009 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $6,359 per guest
? All-inclusive price from $7,349 per guest
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed.
? Cruise only from $6,959 per guest
? All-inclusive price from $7,949 per guest
Classic Suite
Classic Suite
Relax in 400 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Cruise only from $7,619 per guest
? All-inclusive price from $8,609 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs, and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $9,119 per guest
? All-inclusive price from $10,109 per guest
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 - Sun, May 31, 2026
WIND SURF
$5,999
$5,999
Sun, Sep 27 - Wed, Oct 7, 2026
WIND SURF
$7,999
$7,999
Wed, May 19 - Sat, May 29, 2027
STAR LEGEND
$4,989
$3,999
Mon, Jul 5 - Thu, Jul 15, 2027
STAR LEGEND
$4,689
$3,699
THIS
SAILING
Wed, Aug 11 - Fri, Aug 20, 2027
STAR LEGEND
$5,290
$4,399
Tue, Oct 26 - Fri, Nov 5, 2027
STAR LEGEND
$5,689
$4,699