Setting sail from Piraeus, Greece with seas a deep blue and fluffy white clouds floating lazily above Mount Olympus, the city of Athens appears as a granite backdrop to the impending enchantments just over the horizon. We’re aboard Wind Star – long, sleek, with dazzling white sails soaring 200 feet above your head. Standing on deck and gazing down at the animated crowd bidding us bon voyage, it is clear: this stunning vessel commands recognition and respect wherever she sails. Now you’re a part of this reality – or is it a fantasy?
Windstar Cruises operates a fleet of seven intimate luxury cruise ships. It is known for its yacht-style experiences and voyages to the world’s best small ports and hidden harbors, cruising to 50 nations and 100 ports throughout Europe, the South Pacific, the Caribbean, Asia, and Central America. One of the most appealing things about the cruise line’s fleet is that it carries just 148 to 342 guests. Expect fine service and attention to your every need.
On our voyage, a six night sailing between Athens’ port city of Piraeus and Rome’s Civitavecchia, we visited ports such as Greece’s Gythion and Monemvasia and Italy’s Taormina, Sorrento and the island of Capri. In 2026, Star Legend, Windstar’s Star Class yacht, Wind Spirit and Wind Star offer similar voyages, ranging from six to eight nights.
Medieval fortresses and more at Monemvasia
Our first port-of-call was Monemvasia, Greece, is a town inhabited since the sixth century and located on a small peninsula off the east coast of the Peloponnese. After a very long and steep climb, you reach a large plateau hovering above the sea, the site of a medieval fortress and a stunning Byzantine church, the Church of Christ in Chains, with its intricate, carvings of peacocks, a favored symbol of this era. Nearby, another church, the Agia Sofia, has ceilings and walls studded with sparkling mosaics.
During Monemvasia’s Golden Age in the 1400s, wealthy families exported wine, a variety of Madeira, which was actually praised by Shakespeare. Learning that this ancient wine is still served in local trattorias, how could you possibly miss this chance? Finding a medieval-looking café sitting prettily under a stand of orange trees this renowned pink nectar accompanies your dish of freshly-caught (think 2 hours ago) grilled scallops. Rapture.
Back on board, we’re delighted to hear the same music thrumming over the decks that you heard upon first embarking: Vangelis’ Conquest of Paradise, created for 1492, the film. It is grand, majestic, and absolutely perfect for setting sail on a new adventure.
Stalagmite Sculpture
Next: Greece’s Glythion. The town is surrounded by the formidable Taygetos mountain range and adding a bit of romance, Glythion is reputed to have been founded by Heracles and Apollo; their images still appear on its coins. It is recommended that you visit the Diros Caves, first opened in 1963. It’s about 19 miles from the town, and considered one of the most spectacular sites in Greece. You’ll view the glorious, mile-long interior named the “caverns measureless to man” by boat and see forms shaped like well-known icons: There, just ahead in all its tilted glory, the Leaning Tower of Pisa; further on, that mammoth pile has to be the great Chinese Palace. Stalagmites all.
In Taormina, Truman Capote — and you
What can one say about Italy’s Taormina that hasn’t already been said? Truman Capote wrote about it in much of his work and D.H. Lawrence lived in this town’s oldest house, Villa Fontana Vecchia. Its beauty is legend, with the Ionian Sea providing a cinema-worthy backdrop, its ancient theatre the most celebrated ruin in Sicily, and Mount Etna towering over all. You’ll have a happy time navigating Taormina’s narrow, cobblestone streets which are, happily, closed to traffic
Located on Sicily’s East Coast, Taormina is perched on a rocky cliff that overlooks the Ionian Sea. It’s got great views of Mt. Etna, too. The village is, indisputably, one of Sicily’s most sophisticated destinations for fabulous restaurants, upmarket shops and fascinating people-watching along Corso Umberto, its main street, but know this: Its most storied place to visit is the Ancient Theater (Teatro Antico), an excavated, third century BC Greek theater. We also loved time spent in the tranquil public garden of Villa Comunale.
Sorrento is home to Blue Grotto and a famed ballad
Torna A Surriento, “Come Back to Sorrento” is a siren call for this charming town, overlooking Mt. Vesuvius, the isle of Capri, and the Bay of Naples. That song of Sorrento that everyone knows and loves and the images it portrays are all there – the shining sea, the citrus-perfumed gardens, and love – love in the air. It’s there. Sorrento is imbued with echoes of is ancient past and its singular charm lies in its sun-drenched rustic simplicity. Meandering down a maze of medieval alleyways, you’ll visit quaint artisan workshops and perhaps find a tiny, fragrant boutique where you’ll buy luscious lemon soap – and zingy lemon candies! “Come Back to Sorrento” ends by saying to one’s love “come back to Sorrento so my broken heart can mend.”
La Dolce Vita also applies to Capri
This bewitching phrase typically conjures up thoughts of Rome, but for many the concept is also aligned to a fabulous little kernel in the Bay of Naples known as Capri. Sleek black and silver tenders bob close to your ship, ready and waiting to ferry you to this enchanting isle. As we boarded our tender, we could see, in the distance, candy-colored homes built right into steep cliffs forested with oleander, jasmine and bougainvillea. There are the iconic Faraglioni Rocks, seeming to stand guard over this wonderful island. Shopping here is a heady delight. All the top designers are here: Gucci, Bottega Veneta, Prada, Valentino – lofty couture goods with equally lofty price tags.
Our favorite activity, though, was taking a small rowboat to the Blue Grotto. The entrance into the Blue Grotto Cave is so low that you must lie down on the floor of your tiny boat in order to enter, and then there’s the matter of floating into this dark cave. Once inside you’re met with a most spectacular sight as the sunlight is refracted onto the cave’s waters. It’s a luminous blue we’ve seen nowhere else in the world and though you’ll have only about a minute inside to relish its loveliness, the spectacle is something we’ll never forget.
Still more blue? It’s inevitable. We’ve come to the end of your idyll on this Windstar voyage.
As our cruise winds down we do, indeed, feel as if we’ve traveled in equal parts of reality and fantasy. It feels like a dream. And our trip may be over but we know we’ll return often our oft-quirky and colorful ports of call and also to those quiet moments when the engines were off, the sails were up, and the only thing you heard was the sound of the sea.
