Sicilian Splendors
 
Rome to Rome
Mon Sep 22, 2025 - Fri Oct 3, 2025,
 11 days
 on Wind Surf
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Starting from $7,099 USD
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ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

Date
Port
Arrive
Depart
Watersports
Platform
Shore
Excursions
Expand
Mon Sep 22
Rome
Arrive:
Depart:5:00 PM
Watersports Platform: 
6 Available
+_
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.
6 Shore Excursions Available
+
_
Rome, Concierge Collection: Half Day Private CAR with Driverguide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,299
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Rome, Concierge Collection: Half Day Private VAN with Driverguide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,399
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Rome, Concierge Collection: Full Day Private Auto with Driverguide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,799
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Rome, Concierge Collection: Full Day Private VAN with Driverguide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,899
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Rome Orientation Tour w/ Transfer to Airport *Culture | Essentials Collection | Sightseeing | Walking
Duration3 Hours
Activity LevelEasy
$249
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Rome Orientation Tour w/ Transfer to Hotel *Culture | Essentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy
$249
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Tue Sep 23
AT SEA
Arrive:
Depart:
Watersports Platform: 
Wed Sep 24
Giardini Naxos
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
5 Available
+_
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.
5 Shore Excursions Available
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Giardini Naxos, Castelmola & Taormina *Culture | Essentials Collection | Outdoors | Sightseeing | Walking
Duration5 Hours
Activity LevelModerate
$169
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Giardini Naxos, Concierge Collection: Wine Tasting at the Gambino Winery *Concierge Collection | Culture | Refreshments | Wine
Duration4 Hours
Activity LevelModerate-Strenuous
$149
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Giardini Naxos, Taormina On Your Own *Essentials Collection | Outdoors | Sightseeing | Walking
Duration4 Hours
Activity LevelModerate
$89
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Giardini Naxos, Concierge Collection: Half Day Private CAR + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$799
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Giardini Naxos, Concierge Collection: Half Day Private VAN + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$899
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Thu Sep 25
Syracuse, Italy
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
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.
 
 
Fri Sep 26
Gozo
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
2 Available
+_
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.
2 Shore Excursions Available
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Gozo, 4x4 Safari *Beach | Essentials Collection | Outdoors | Sightseeing
Duration5 Hours
Activity LevelModerate
$139
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Gozo, Highlights of Gozo *Culture
Duration4 Hours
Activity LevelStrenuous
$99
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Sat Sep 27
Valletta
Arrive:12:01 AM
Depart:6:00 PM
Watersports Platform: 
7 Available
+_
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. 
7 Shore Excursions Available
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Valletta, Concierge Collection: Half Day Private Car *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$499
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Valletta, Concierge Collection: Half Day Private Van *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$599
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Valletta, Concierge Collection: Full Day Private Car *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$799
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Valletta, Concierge Collection: Full Day Private Van *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$899
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Valletta, Concierge Collection: The Maltese Cooking ExperienceConcierge Collection | Culture | Dining
Duration3.5 Hours
Activity LevelEasy-Moderate
$229
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Valletta, Mdina's Noble HeritageCulture | Essentials Collection | Sightseeing | Refreshments | Walking | Wine
Duration5 Hours
Activity LevelModerate-Strenuous
$139
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Valletta & Three Cities Boat Ride *Boating | Essentials Collection | Sightseeing | UNESCO | Walking
Duration4 Hours
Activity LevelModerate-Strenuous
$129
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Sun Sep 28
Porto Empedocle
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
6 Available
+_
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. 
6 Shore Excursions Available
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Porto Empedocle, Half Day Private Car w/Driver & GuideConcierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$699
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Porto Empedocle, Half Day Private Van w/Driver & GuideConcierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$799
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Porto Empedocle, Full Day Private Car w/Driver & GuideConcierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy-Moderate
$999
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Porto Empedocle, Full Day Private Van w/Driver & GuideConcierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy-Moderate
$1,199
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Porto Empedocle, A Taste of Sant'Angelo MuxaroCulture | Sightseeing | Refreshments
Duration3.25 Hours
Activity LevelModerate
$199
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Porto Empedocle, Temples Valley *Essentials Collection | Sightseeing | UNESCO
Duration3.5 Hours
Activity LevelModerate
$129
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Mon Sep 29
Trapani
Arrive:8:00 AM
Depart:4:00 PM
Watersports Platform: 
5 Available
+_
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. 
5 Shore Excursions Available
+
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Trapani, Erice *Essentials Collection | Sightseeing | Walking
Duration4 Hours
Activity LevelModerate-Strenuous
$129
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Trapani, Concierge Collection: Erice & Cooking Class at Palazzo Nuara *Concierge Collection | Culture | Dining | Sightseeing | Walking
Duration6 Hours
Activity LevelModerate
$229
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Trapani, Marsala and Lite Lunch at Cantine Pellegrino *Dining | Essentials Collection | Sightseeing | Walking | Wine
Duration5.5 Hours
Activity LevelModerate
$189
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Trapani, Segesta’s Ancient WondersCulture | Essentials Collection | Sightseeing
Duration4 Hours
Activity LevelModerate
$149
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Trapani, Walking Tour with Sicilian Coffee Break *Essentials Collection | Outdoors | Sightseeing | Refreshments | Walking
Duration3 Hours
Activity LevelModerate
$59
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Tue Sep 30
Lipari
Arrive:8:00 AM
Depart:4:00 PM
Watersports Platform: 
4 Available
+_
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. 
4 Shore Excursions Available
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Lipari, Concierge Collection: Lipari by Bike *Biking | Concierge Collection | Sightseeing
Duration3 Hours
Activity LevelStrenuous
$159
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Lipari, Lipari Walking Tour *Essentials Collection | Sightseeing | Refreshments | Walking
Duration2.5 Hours
Activity LevelStrenuous
$55
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Lipari Island and Pizza Demonstration *Culture | Dining | Essentials Collection | Sightseeing | Wine
Duration4.5 Hours
Activity LevelModerate
$139
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Lipari Highlights *Essentials Collection | Sightseeing | Refreshments
Duration3 Hours
Activity LevelModerate
$89
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Wed Oct 1
Sorrento
Arrive:8:00 AM
Depart:11:59 PM
Watersports Platform: 
11 Available
+_
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. 
11 Shore Excursions Available
+
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Sorrento, Concierge Collection: Half Day Private Car with Driver & Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,199
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Sorrento, Concierge Collection: Half Day Private Van with Driver & Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,399
VIEW DETAILS
Sorrento, Concierge Collection: Full Day Private Car with Driver & Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,499
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Sorrento, Concierge Collection: Full Day Private Van with Driver & Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,519
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Sorrento, Concierge Collection: Positano & Amalfi by Private Speed Boat, for 6 GuestsBoating | Concierge Collection | Sightseeing | UNESCO | Walking
Duration8 Hours
Activity LevelEasy
$3,999
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Sorrento, Boat Tour to Positano *Boating | Essentials Collection | Sightseeing | Walking
Duration5 Hours
Activity LevelModerate
$259
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Sorrento, Discovery & Tasting *Essentials Collection | Sightseeing | Refreshments | Wine
Duration4 Hours
Activity LevelEasy
$115
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Sorrento, Concierge Collection: Sorrento Gourmet *Concierge Collection | Dining | Sightseeing | Walking
Duration5.5 Hours
Activity LevelEasy
$419
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Sorrento, Herculaneum *Culture | Essentials Collection | Sightseeing | UNESCO | Walking
Duration5.5 Hours
Activity LevelModerate
$179
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Sorrento, Journey to Pompeii *Culture | Essentials Collection | Sightseeing | UNESCO | Walking
Duration5.5 Hours
Activity LevelModerate-Strenuous
$189
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Sorrento, Concierge Collection: Positano by Private Speedboat, for 6 GuestsBoating | Concierge Collection | Sightseeing | Walking
Duration4 Hours
Activity LevelEasy
$3,299
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Thu Oct 2
Amalfi
Arrive:7:00 AM
Depart:2:00 PM
Watersports Platform: 
5 Available
+_
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.
5 Shore Excursions Available
+
_
Amalfi, Concierge Collection: Half Day Private Car + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,199
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Amalfi, Concierge Collection: Half Day Private Van + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,299
VIEW DETAILS
Amalfi, Pompeii *Culture | Essentials Collection | Sightseeing | UNESCO | Walking
Duration5.5 Hours
Activity LevelModerate-Strenuous
$179
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Amalfi, Positano By Boat *Boating | Culture | Essentials Collection | UNESCO | Walking
Duration4 Hours
Activity LevelModerate-Strenuous
$89
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Amalfi, Highlights of Ravello & Amalfi *Culture | Essentials Collection | Outdoors | Sightseeing | Walking
Duration4 Hours
Activity LevelModerate-Strenuous
$139
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Fri Oct 3
Rome
Arrive:7:00 AM
Depart:
Watersports Platform: 
6 Available
+_
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.
6 Shore Excursions Available
+
_
Rome, Concierge Collection: Half Day Private CAR with Driverguide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,299
VIEW DETAILS
Rome, Concierge Collection: Half Day Private VAN with Driverguide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,399
VIEW DETAILS
Rome, Concierge Collection: Full Day Private Auto with Driverguide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,799
VIEW DETAILS
Rome, Concierge Collection: Full Day Private VAN with Driverguide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,899
VIEW DETAILS
Rome Orientation Tour w/ Transfer to Airport *Culture | Essentials Collection | Sightseeing | Walking
Duration3 Hours
Activity LevelEasy
$249
VIEW DETAILS
Rome Orientation Tour w/ Transfer to Hotel *Culture | Essentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy
$249
VIEW DETAILS