SAILING GREECE & ITALY ABOARD WINDSTAR’S STAR LEGEND
By Sharon K. Kurtz

The moment I stepped aboard Windstar Cruises’ Star Legend in Athens, I left behind more than my suitcase. For the next eight days, there would be no hotel check-ins, no train schedules and no rushing from one destination to the next. Instead, Star Legend became my floating home, carrying me from Greece to Italy as I stepped directly into centuries-old harbor towns, lingered over long lunches in Sicily, shopped with the ship’s executive chef in a bustling Sardinian market and watched Mediterranean sunsets from the deck.

It wasn’t simply the destinations that made this journey memorable. It was the way I experienced them.

Windstar specializes in small-ship destination immersion rather than onboard attractions. Unlike the massive cruise ships that dock far from city centers, Windstar’s small ships slip into ports many larger vessels can’t reach. That meant more time exploring and less time commuting. Throughout the voyage, I walked straight from the gangway into lively piazzas, waterfront cafés and historic neighborhoods.

The itinerary, A Piece of Greece, a Slice of Italy, proved that sometimes the journey between destinations can be just as rewarding as the destinations themselves. That’s the philosophy behind Windstar Cruises, whose yacht-style ships are designed to spend less time at sea and more time immersed in the destinations themselves.

Boutique Ship, Big Experience
Carrying just 312 guests, Star Legend feels more like a private yacht than a traditional cruise ship. Crew members quickly learned my name, remembered how I liked my morning coffee and greeted me throughout the voyage.

 The smaller size also created a relaxed atmosphere. There were no long lines, crowded buffets or frantic searches for deck chairs. Instead, I found quiet corners to read, panoramic lounges, sunset cocktails and inviting outdoor spaces where fellow travelers naturally gathered to share stories of the day’s adventures.

 The intimate scale extends to the service. With nearly 190 crew members caring for just 312 guests, the atmosphere feels personal from the moment you step aboard.

Windstar Star Legend at a Glance
Ship: Star Legend
Guests: 312
Crew: Approximately 190
Accommodations: All-suite yacht
Dining: Six complimentary dining venues
Cuisine: James Beard Foundation culinary partnership
Wellness: Complimentary sauna, steam room and thermal loungers
Marina: Complimentary watersports platform (available where conditions permit)

Ports Beyond the Ordinary
One of the greatest advantages of a small ship is access.

Rather than spending hours traveling from industrial cruise terminals into city centers, the ship docked within walking distance of the places I had come to experience. In Greece, I wandered charming waterfront streets before most visitors had arrived. In Italy, I stepped directly into historic harbor towns where cafés, churches and lively markets awaited just beyond the pier.

Because embarkation and disembarkation were so effortless, I often returned to the ship for lunch or a brief rest before heading back ashore in the evening. That flexibility made every destination feel less hurried and far more immersive.

Why Shoulder Season Changes Everything
I’ve traveled Europe during the busy summer months, but this voyage reminded me why spring and fall are among the best times to visit the Mediterranean.

 Mystras, Greece, felt almost timeless. As I climbed the winding stone paths through the remarkably preserved Byzantine city overlooking Sparta, fresco-filled churches, monasteries and palace ruins emerged from the hillside. Without summer crowds, I could pause to absorb the sweeping valley views and imagine life here centuries ago.

In Corfu’s UNESCO-listed Old Town, Venetian architecture, flower-filled balconies and narrow cobblestone lanes invited slow exploration. Instead of weaving through tour groups, I lingered in neighborhood cafés, watched locals gather in leafy squares and joined families enjoying the evening passeggiata beneath the graceful arcades of the Liston.

Taormina, Sicily, may be one of the Mediterranean’s most photographed towns, but shoulder season allowed me to experience it at a leisurely pace. I spent far longer than planned inside the spectacular Greco-Roman Theatre, where Mount Etna rises dramatically beyond the ancient stone stage while the Ionian Sea stretches to the horizon. It was one of those unforgettable views that deserves time.

Our stop in Cagliari, Sardinia, revealed another side of the Mediterranean. Walking the fortified sea walls, browsing artisan shops and wandering through the Catalan-influenced old town before joining Windstar’s market excursion offered a wonderful introduction to the island’s distinct culture and cuisine.

 By the end of the voyage, I realized shoulder season had quietly become one of the trip’s greatest luxuries. Comfortable temperatures, fewer crowds and softer light made every destination feel more relaxed. Restaurants were easier to enjoy, conversations with locals unfolded naturally and photography became far more rewarding.

Why Choose Shoulder Season?
·        Comfortable temperatures ideal for sightseeing

·        Smaller crowds at popular attractions

·        Better photography with softer natural light

·        Easier reservations at restaurants and attractions

·        More authentic interactions with residents

·        Often better cruise fares than peak summer

A Taste of Greece and Sicily
Some of my favorite memories came through food.

Every destination offered a taste of its own culinary traditions. In Greece, leisurely lunches featured crisp village salads topped with creamy feta, grilled octopus, fresh-caught fish, lamb, flaky spanakopita and warm pita served with tangy tzatziki. Local olive oils, briny Kalamata olives and glasses of crisp Assyrtiko wines reflected the country’s deep connection to the land and sea.

By the time I reached Sicily, the flavors shifted once again. Fresh seafood, handmade pasta, citrus, capers, sweet cannoli and rich olive oils reflected centuries of Greek, Arab, Norman and Spanish influence. Local wines, including crisp Grillo and mineral-driven Etna Bianco, paired beautifully with leisurely meals enjoyed in family-owned restaurants and bustling piazzas.

Rather than simply checking off famous landmarks, I found myself lingering over long lunches, discovering that some of the Mediterranean’s most memorable experiences happen around the table. Those meals became as meaningful as any historic site I visited.

Shopping With the Executive Chef in Sardinia
One of Windstar’s signature experiences took me beyond sightseeing and into everyday local life.

 Joining Executive Chef Neil Romulus at a bustling Sardinian market offered a fascinating look at how the ship sources regional ingredients. As vendors proudly displayed seasonal produce, cheeses, fresh seafood and fragrant herbs, Chef Neil explained how local traditions influence the menus served onboard.

 Watching him select ingredients—and later seeing them transformed into dinner that evening—created a meaningful connection between the destination and the dining experience. It was an excursion that appealed equally to food lovers and curious travelers.

Dining That Reflects the Destination
Cuisine plays a central role throughout the Windstar experience.

Menus change frequently to showcase regional flavors, and ingredients sourced in port often appear onboard within hours. Fresh seafood, local wines, artisanal cheeses and seasonal produce created meals that reflected wherever we happened to be sailing.

 Whether enjoying breakfast on the open deck, lingering over lunch outdoors or savoring a multi-course dinner in the elegant dining room, every meal reinforced the feeling that this voyage celebrated the Mediterranean as much through its cuisine as through its scenery.

 Life at Sea
The beauty of a small ship isn’t only found ashore.

 Sea days became opportunities to slow down. I watched islands drift across the horizon from a comfortable lounge chair, attended enrichment presentations, enjoyed conversations with fellow travelers and appreciated the luxury of having nowhere urgent to be.

 My husband and I often ended the day on deck, watching the sun sink below the horizon with a glass of wine in hand. Those quiet moments at sea became just as memorable as the ports themselves.

Unlike larger ships packed with constant entertainment, Star Legend embraces a quieter rhythm. The emphasis remains on the destinations, the people you meet and the simple pleasure of being at sea.

Why Small Ships Change the Way You Travel
By the end of the voyage, I realized I had experienced the Mediterranean differently than on any previous trip.

 Rather than racing between iconic attractions, I settled into the rhythm of coastal life. I lingered longer, walked farther and discovered places that felt authentic rather than crowded.

 For travelers who value culture, cuisine, meaningful connections and easy access to remarkable destinations, a small-ship cruise offers far more than transportation. It becomes part of the destination itself.

That’s what made A Piece of Greece, a Slice of Italy so memorable. I didn’t simply visit the Mediterranean—I settled into its rhythm. Each port invited me to slow down, linger a little longer and experience daily life rather than merely checking destinations off a list. That’s the quiet luxury of small-ship cruising, and it’s why I can’t imagine exploring the Mediterranean any other way.

Plan Your Own Windstar Mediterranean Voyage
Ready to experience A Piece of Greece, a Slice of Italy or another Windstar itinerary? Visit Windstar Cruises to explore Mediterranean voyages, special offers and booking information.


Sharon Kurtz is an Austin-based freelance travel writer and award-winning photographer. She is passionate about exploring the world and sharing her experiences through captivating storytelling. She is an active member of The Society of American Travel Writers (SATW) and The International Food, Wine, and Travel Writers Association (IFWTWA).

Follow her travels on:
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