14 nights · Greece · Departs Piraeus-Athens (Greece) · Visiting Syros Island, Kusadasi, Samos Island, Naxos Island, Folegandros Island, Milos Island, Mykonos Island, Patmos Island, Santorini Island, Monemvasia, Nafplio · Aboard Windstar Cruises on the Wind Surf
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Wind Surf |
| Duration | 14 nights |
| Port calls | 12 |
| Departures | 3 sailings |
| From fare | $5,541 per person |
| Year built | 1990 |
| Guests | 376 |
| Cabins | 171 |
| Crew | 178 |
| Length | 187 m |
| Beam | 20 m |
| Cruising speed | 15.0 kn |
Piraeus is Athens’ working harbour, not a resort port—and that is its appeal. From here, the capital’s ancient landmarks are within reach, while the waterfront keeps its own busy, distinctly Greek character. Visit the Archaeological Museum of Piraeus, then linger over grilled fish in Mikrolimano, a small harbour lined with tavernas. Metro connections make central Athens straightforward. Or stay near the water and watch ferries depart for the islands.
Above Ermoupoli’s busy harbor, Áno Sýros keeps the quieter face of Syros. Its medieval lanes climb toward the Catholic Cathedral of Saint George, past whitewashed houses and small tavernas. Go on foot in shoes with grip, pausing for views across the Aegean and down to the neoclassical capital. This is a place for unhurried exploring, not a beach day.
Kuşadası puts the Aegean within reach, with a lively waterfront and one of Turkey’s most celebrated ancient cities nearby. Ephesus lies about 20 kilometres inland, where marble avenues lead to the Library of Celsus and Great Theatre. Back in town, browse the bazaar, then follow the causeway to Pigeon Island and its historic fortress. The harbour-facing promenade offers an easy place to linger over the Aegean light.
On Samos, one of Greece’s easternmost Aegean islands, ancient history sits close to the sea. From the port, reach Pythagoreion, the birthplace of Pythagoras and a UNESCO-listed harbor town with a long trading history. Nearby, the monumental Heraion recalls the island’s importance in the ancient Greek world. Taste fragrant Samos Muscat, browse Vathy’s waterfront, or follow coastal roads to pebble coves and villages beneath Mount Kerkis.
Naxos is the largest island in the Cyclades, yet its pleasures feel refreshingly unhurried. From the harbor, the marble Portara frames the sea, while the Venetian Kastro rises above the old town’s narrow lanes. Beyond town, villages such as Halki reveal Byzantine churches, citrus groves, and the island’s distinctive kitron liqueur. Golden beaches, mountain roads, and excellent tavernas make Naxos worth exploring beyond the waterfront.
Folegandros welcomes you at Karavostasis, a small harbour on one of the Cyclades’ most striking islands. From here, a winding road climbs to Chora, where whitewashed lanes surround a medieval kastro above the sea. Continue to the Church of Panagia for sweeping views across cliffs and blue water. Then settle into a square-side taverna or seek a swim at a secluded cove.
Arrive at Adamas, Milos’s sheltered ferry port, and you step onto an island shaped by fire and sea. Its volcanic geology has carved pale cliffs, sea caves, and beaches across the coast. Visit Sarakiniko’s sculpted white rock, then climb to Plaka for island-wide views and a quiet evening. At Tripiti, visit the early Christian catacombs and ancient theater, near where the Venus de Milo was found in 1820.
Piraeus is Athens’ working harbour, not a resort port—and that is its appeal. From here, the capital’s ancient landmarks are within reach, while the waterfront keeps its own busy, distinctly Greek character. Visit the Archaeological Museum of Piraeus, then linger over grilled fish in Mikrolimano, a small harbour lined with tavernas. Metro connections make central Athens straightforward. Or stay near the water and watch ferries depart for the islands.
Mykonos rewards an early start: whitewashed lanes, blue-domed churches and waterfront cafés are quieter before the cruise crowds arrive. In Little Venice, old captains’ houses lean over the Aegean, while the island’s windmills stand above the harbor. Beyond town, beaches range from lively Psarou to the broad sands of Elia. Take a short boat ride to Delos, where ancient sanctuaries and marble streets mark one of Greece’s great archaeological sites.
Kuşadası puts the Aegean within reach, with a lively waterfront and one of Turkey’s most celebrated ancient cities nearby. Ephesus lies about 20 kilometres inland, where marble avenues lead to the Library of Celsus and Great Theatre. Back in town, browse the bazaar, then follow the causeway to Pigeon Island and its historic fortress. The harbour-facing promenade offers an easy place to linger over the Aegean light.
Patmos, a small Dodecanese island, pairs a quiet harbour with a remarkable religious history. From Skala, a winding road climbs to Chora, where whitewashed lanes lead to the Monastery of Saint John. Nearby, the Cave of the Apocalypse recalls the tradition that John received the visions behind Revelation. These UNESCO-listed sites reward a visit; beaches and waterfront tavernas offer a gentler counterpoint.
Few Greek islands make an entrance like Santorini, where whitewashed villages crown a volcanic caldera above the Aegean. Most cruise ships anchor offshore, and tenders land at the old port below Fira. Ride the cable car, or climb the steps, to reach the island’s capital and its celebrated views. Beyond Fira, Oia’s blue domes, the archaeological site of Akrotiri, and volcanic wines reward a longer day ashore.
Monemvasia rises from the sea as a sheer rock, joined to the Peloponnese by a narrow causeway. Step through its medieval gate into a stone-built town of vaulted lanes, Byzantine churches and Venetian-era mansions. Cars stay outside the lower town, leaving its steep alleys to walkers. Climb to the ruined upper fortress for wide views across the Aegean, then return for local wine and seafood.
Nafplion is the Peloponnese at its most inviting: a seafront town shaped by Venetian, Ottoman and Greek histories. In the old quarter, cobbled lanes lead to Syntagma Square, lined with historic façades and cafés. Above the rooftops, Palamidi Fortress commands the view; offshore, Bourtzi guards the harbor. Come ashore for a compact, walkable city, then linger over lunch beside the water.
Piraeus is Athens’ working harbour, not a resort port—and that is its appeal. From here, the capital’s ancient landmarks are within reach, while the waterfront keeps its own busy, distinctly Greek character. Visit the Archaeological Museum of Piraeus, then linger over grilled fish in Mikrolimano, a small harbour lined with tavernas. Metro connections make central Athens straightforward. Or stay near the water and watch ferries depart for the islands.
Published August 25, 2026
Last updated October 3, 2026
Author: J. Richard
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