Star Collector: Mediterranean Masterpieces of Italy & Northern Greece
 
Rome to Athens, Greece
Sat Sep 19, 2026 - Sat Oct 3, 2026,
 14 days
 on Star Legend
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Starting from $6,999 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
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Sat Sep 19
Rome
Arrive:
Depart:4:00 PM
Watersports Platform: 
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.
Sun Sep 20
Sorrento
Arrive:8:00 AM
Depart:5:00 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
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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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Mon Sep 21
Messina (Taormina)
Arrive:9:00 AM
Depart:5:00 PM
Watersports Platform: 
7 Available
+_
The cobblestone streets of Messina, Sicily, are the perfect launching point for an optional visit to nearby Taormina. Stroll along flower-filled streets in search of a delightful lunch or an artist’s palette of colorful gelati. The ancient Greek Theater is an ideal place to sit back and admire shimmering waters below and Mount Etna, languidly smoking in the distance.
7 Shore Excursions Available
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Messina, Concierge Collection: Half Day Private Car & Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$799
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Messina, Concierge Collection: Half Day Private Van & Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$899
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Messina, Classic Taormina *Essentials Collection | Sightseeing
Duration5 Hours
Activity LevelModerate
$129
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Messina, In the Steps of the Godfather *Culture | Essentials Collection | Sightseeing | Walking
Duration5 Hours
Activity LevelStrenuous
$115
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Messina, Messina Walking Tour *Essentials Collection | Walking
Duration2.5 Hours
Activity LevelModerate
$59
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Messina, Scenic Mt EtnaEssentials Collection | Sightseeing | Refreshments | UNESCO | Walking
Duration4.5 Hours
Activity LevelModerate-Strenuous
$99
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Messina, Wine Tasting at Gambino Winery *Essentials Collection | Refreshments | Wine
Duration5 Hours
Activity LevelModerate-Strenuous
$159
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Tue Sep 22
AT SEA
Arrive:
Depart:
Watersports Platform: 
Wed Sep 23
Gythion
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
7 Available
+_
Cheerful pastel houses are littered among intriguing whitewashed lanes and staircases. Playful sculptures welcome you to the harbor’s cheerful shops, coffee houses, and waterfront cafés. This is a perfect place to enjoy a cup of rich coffee or a glass of ouzo while you watch the world go by.  Or go exploring on an optional tour of Mystras, a UNESCO World Heritage Site. 
7 Shore Excursions Available
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Gythion, Mystras Byzantine City *Culture | Essentials Collection | UNESCO
Duration4 Hours
Activity LevelModerate-Strenuous
$159
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Gythion, Dyros Caves *Culture | Essentials Collection | Outdoors
Duration4 Hours
Activity LevelModerate
$159
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Gythion, Sparta & Mystra with Olive Oil MuseumEssentials Collection | Refreshments | UNESCO | Walking
Duration5 Hours
Activity LevelModerate-Strenuous
$159
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Gythion, Concierge Collection: Half Day Private CAR+ Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,099
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Gythion, Concierge Collection: Half Day Private VAN + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,399
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Gythion, Concierge Collection: Full Day Private CAR + Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,599
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Gythion, Concierge Collection: Full Day Private VAN + Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,799
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Thu Sep 24
Monemvasia
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
6 Available
+_
This Gibraltar-like town tied to the mainland by a single thread of causeway holds treasures that are old even by Mediterranean standards, with town walls and several churches dating to the 12th century. Climb to the upper town for an up-close look at the castle and Agia Sophia, a Byzantine church. Wander the lanes of the lower town lined with Venetian mansions, many of which have been lovingly restored. Savor the sun on a smooth pebble beach. 
6 Shore Excursions Available
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Monemvasia Castle *Essentials Collection | Sightseeing | Walking
Duration3 Hours
Activity Level(not specified)
$129
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Monemvasia, Concierge Collection: Castle & Liotrivi Olive Oil Factory *Concierge Collection | Dining | Sightseeing | Walking
Duration4.5 Hours
Activity LevelModerate
$169
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Monemvasia, Concierge Collection: Half Day Private CAR + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,365
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Monemvasia, Concierge Collection: Half Day Private VAN + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$1,469
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Monemvasia, Concierge Collection: Full Day Private CAR + Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,575
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Monemvasia, Concierge Collection: Full Day Private VAN + Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$1,785
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Fri Sep 25
Athens, Greece
Arrive:7:00 AM
Depart:5:00 PM
Watersports Platform: 
With 3,000 years of history, you can’t turn around in Athens without encountering the past. The Acropolis, a UNESCO site, the Plaka, and the Acropolis Museum are must-sees. But leave time if you can to climb Pnyx Hill for photos of the Parthenon at sunset, to buy your own set of Greek komboloi (worry beads), and to explore the metro stations that serve as mini-museums for the relics that are constantly being unearthed. 
Sat Sep 26
Kusadasi
Arrive:10:00 AM
Depart:11:59 PM
Watersports Platform: 
7 Available
+_
Few places offer such a rich combination of history and scenic beauty. In Ephesus, one of the greatest outdoor museums in the world, you’ll explore legendary sites steeped in history. Also visit the houses of Bulbul Mountain, where the roof of one forms the terrace of the next. This evening we present our Destination Discovery Event -- dinner in the moonlight and a concert near the  Celsus Library or on Harbour Street in ancient Ephesus. 

 
7 Shore Excursions Available
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Kusadasi, Ephesus & Ancient Houses *Culture | Essentials Collection | Sightseeing | UNESCO | Walking
Duration4 Hours
Activity LevelModerate-Strenuous
$79
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Kusadasi, Archaeological Ephesus & Museum *Culture | Essentials Collection | Sightseeing | Refreshments | UNESCO | Walking
Duration5 Hours
Activity LevelModerate
$79
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Kusadasi, Concierge Collection: Ephesus & Private Lunch at Sirince Village *Concierge Collection | Culture | Dining | UNESCO | Walking | Wine
Duration7 Hours
Activity LevelModerate-Strenuous
$135
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Kusadasi, Ephesus and Virgin Marys HouseCulture | Essentials Collection | Outdoors | UNESCO | Walking
Duration5 Hours
Activity LevelModerate
$79
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Kusadasi, Concierge Collection: Half Day Private VAN + Guide *Concierge Collection | Sightseeing
Duration4 Hours
Activity LevelEasy
$599
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Kusadasi, Concierge Collection: Full Day Private VAN + Guide *Concierge Collection | Sightseeing
Duration8 Hours
Activity LevelEasy
$899
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Kusadasi, Best of Ephesus *Culture | Dining | Essentials Collection | Sightseeing | UNESCO | Walking
Duration7.5 Hours
Activity LevelModerate-Strenuous
$119
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Sun Sep 27
AT SEA
Arrive:
Depart:
Watersports Platform: 
Mon Sep 28
Kavala, Greece
Arrive:8:00 AM
Depart:9:30 PM
Watersports Platform: 
Kavala, a vibrant port city in northern Greece, is known for its rich history and stunning coastal scenery. The city's landscape is dominated by the imposing Kavala Castle, offering panoramic views of the Aegean Sea. The historic old town, with its narrow streets and traditional houses, reflects Kavala's Ottoman and Byzantine heritage. Kavala is also known for its local cuisine – make sure you try traditional dishes, like kovourmas (cured meat), soutzoukakia (spiced meatballs), and local cheeses.
Tue Sep 29
Thessaloniki, Greece
Arrive:12:00 PM
Depart:
Watersports Platform: 
Thessaloniki, Greece's second-largest city, is a vibrant cultural and historical hub. The city boasts numerous landmarks, including the iconic White Tower, the Rotunda, and the Arch of Galerius. The Byzantine Walls, a remnant of the city's ancient fortifications, offer panoramic views and lead to the impressive Trigonian Tower, a key defensive structure.  Nearby, the archaeological site of Vergina, home to the royal tombs of Macedonian kings, adds to the city's historical allure. Thessaloniki also has a lively waterfront lined with cafes, bars, and restaurants, offering stunning views of the Thermaic Gulf.
Wed Sep 30
Thessaloniki, Greece
Arrive:
Depart:6:00 PM
Watersports Platform: 
Thessaloniki, Greece's second-largest city, is a vibrant cultural and historical hub. The city boasts numerous landmarks, including the iconic White Tower, the Rotunda, and the Arch of Galerius. The Byzantine Walls, a remnant of the city's ancient fortifications, offer panoramic views and lead to the impressive Trigonian Tower, a key defensive structure.  Nearby, the archaeological site of Vergina, home to the royal tombs of Macedonian kings, adds to the city's historical allure. Thessaloniki also has a lively waterfront lined with cafes, bars, and restaurants, offering stunning views of the Thermaic Gulf.
Thu Oct 1
Volos, Greece
Arrive:9:00 AM
Depart:9:00 PM
Watersports Platform: 
Volos is known for its picturesque waterfront and vibrant cultural scene. Nestled at the foot of Mount Pelion and serving as the gateway to the Pelion Peninsula, Volos offers stunning views and easy access to beautiful beaches, lush forests, and charming mountain villages. The city's promenade is lined with lively cafes, restaurants, and bars, perfect for enjoying local cuisine and fresh seafood. Volos is only a few hours' drive from the breathtaking Meteora Monasteries, a UNESCO World Heritage site. These ancient monasteries, perched atop towering rock formations, blend spiritual history with awe-inspiring natural beauty.
Fri Oct 2
Skopelos, Greece
Arrive:8:00 AM
Depart:4:00 PM
Watersports Platform: 
Skopelos is an island known for its lush green landscapes, blue waters, and charming whitewashed villages. The setting for the film, Mamma Mia!, Skopelos exudes a serene and laid-back beauty that captivates visitors. The island's coastline is dotted with idyllic beaches, including the famous Kastani Beach, with its golden sands and clear waters. The main town, Skopelos Town, charms with its narrow cobblestone streets, traditional tavernas, and quaint shops. History echoes through ancient churches and monasteries scattered across the island.
Sat Oct 3
Athens, Greece
Arrive:7:00 AM
Depart:
Watersports Platform: 
With 3,000 years of history, you can’t turn around in Athens without encountering the past. The Acropolis, a UNESCO site, the Plaka, and the Acropolis Museum are must-sees. But leave time if you can to climb Pnyx Hill for photos of the Parthenon at sunset, to buy your own set of Greek komboloi (worry beads), and to explore the metro stations that serve as mini-museums for the relics that are constantly being unearthed.