Small Wonder: Sailing the Mediterranean Aboard Wind Spirit
Forget megaships: the 148-guest Wind Spirit trades crowds for connection and quiet luxury on a weeklong Mediterranean voyage from Rome to Athens.
By Lori Capullo
There is something undeniably romantic about arriving in a destination under sail. Long before the era of floating resorts and megaships, travelers crossed the seas propelled by wind, guided by the horizon and a spirit of adventure. That tradition lives on aboard Wind Spirit, the elegant four-masted sailing yacht operated by Windstar Cruises, and nowhere does it captivate more than in the Mediterranean.
Over the course of a week, we traced a route along Italy’s Amalfi Coast and Sicily before crossing the Ionian Sea to Greece, with picturesque harbors, dramatic cliffs, ancient ruins, and quaint seaside villages always in our sights. From the moment the yacht cast off, it was clear this would be a different kind of voyage.
Getting there started with a bump. My luggage didn’t arrive in Rome from Miami, even though my husband’s bag traveled alongside it from MIA and neon-yellow “Priority” stickers plastered both suitcases. What followed was an adventure before we ever boarded. We raced through the streets of Rome scooping up clothing, shoes, and a replacement suitcase, and the scramble felt more comical than stressful.
We completed the mission in the three-hour window between the stores opening their doors and our taxi ride to Civitavecchia, where the yacht awaited. Once aboard Wind Spirit, the luggage troubles faded into the background.
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What Is It Like to Arrive in Amalfi Under Sail?
Our first major stop was Amalfi, one of the jewels of Italy’s celebrated Amalfi Coast. Approaching from the sea offers a perspective that land-based visitors never get. Colorful buildings cling impossibly to steep mountainsides, while church towers rise among lemon groves and terraced gardens.
The town itself is compact and inviting. Narrow lanes wind through centuries-old neighborhoods where cafés spill onto cobblestone streets and shops display jewelry, handmade ceramics, and leather goods in every shade of the rainbow.
Then there is the food. Plates of pasta and pizza filled café tables up and down every street, but lemon sorbet steals the culinary show. In Amalfi, lemons aren’t just a local crop—the town carries on a full-blown love affair with the citrus, from candies and sorbet to limoncello and lemon-themed merchandise.
We happened to visit during the Festa del Lavoro (Labor Day), so Italians turned out in full force alongside the tourists. They sprawled on the black-sand beaches despite temps of 68 degrees Fahrenheit, frolicked in the water, and clogged the streets, gigantic sorbet-filled lemons in hand.
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The imposing Cathedral of Saint Andrew dominates the central piazza, its striped façade and grand staircase a reminder of Amalfi’s importance during the Middle Ages. I perched outside and pondered its history as I nursed my own sweet, tangy treat.
Unlike larger vessels, Wind Spirit lets guests feel closely connected to the places they visit. Tenders carried us ashore and back, and by late afternoon the town glowed in golden sunlight as the yacht waited offshore, her masts silhouetted against the cliffs in a scene worthy of a classic travel poster.
Taormina: Sicily's Timeless Treasure
From the Amalfi Coast, our voyage continued south to Sicily and the beautiful hilltop town of Taormina. Arriving by sea, we enjoyed views of Mount Etna rising in the distance. The active volcano dominates the horizon and adds drama to an already spectacular setting.
Taormina has long attracted artists, writers, and travelers seeking inspiration, and it’s easy to understand why. Elegant buildings, flowering balconies, and inviting cafés line its historic streets. The town’s crown jewel is the ancient Greek Theatre, perched high above the coastline with breathtaking views of the Ionian Sea.
We got the backstory on the city, and on Sicily as a whole, from our tour guide, Nunzio Bruno. A born-and-raised Sicilian with a wicked sense of humor, he runs Sicily Wonders tours and possesses an intense knowledge of his homeland and its evolution through the centuries.
Nunzio covered everything from the black-fleshed, poisonous oranges we ooh-ed and aah-ed over as we drove past to the 19th-century origins of the Mafia, which, in his telling, began almost as a shadow government that protected local families and their land.
Crossing the Ionian Sea to Greece
The crossing from Sicily to Greece gave us a chance to slow down and appreciate the voyage itself. For most of the 148 guests aboard, that meant lounging poolside or around the hot tub, catching the breeze from a lounge chair or sofa on deck, sipping a cocktail, and taking in the live music.
Life Aboard Wind Spirit
Chilling in the cabin is, of course, also an option. The guest quarters are roomy and meticulous, with banquettes for enjoying the 24-hour room service or, should insomnia kick in, a movie on the flatscreen.
Guests can also indulge in a treatment or two at the Elemis Spa, a quiet, elegant oasis amid the activity that ensues when everyone is aboard at once. It makes a relaxing precursor to dinner in the AmphorA dining room, which transitions from a sun-dappled space by day to a dimly lit, casually elegant spot at night.
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Each night brings specials from James Beard Award–winning chefs. I enjoyed a strawberry gazpacho one evening and wouldn’t have minded seconds, and the regular menu offers sesame-crusted tuna, lamb chops, seafood pasta, and vegetarian options. The ambience feels intimate and elegant without being fussy, and there’s no assigned seating or set mealtime, which we appreciated.
Candles serves breakfast and lunch during the day. At dinner, its steaks, skewers, and fish dishes are best enjoyed as the sun sets through the vast windows.
Gythion: Gateway to Ancient Greece
Our arrival in Gythion introduced us to a lesser-known side of Greece. Unlike Amalfi, it felt sleepy and tranquil, with endless water views. On the Peloponnese Peninsula, fishing boats line the harbor town’s waterfront, colorful neoclassical buildings overlook the harbor, and local tavernas warmly welcome visitors.
The surrounding region offers access to remarkable archaeological sites and landscapes, including the Byzantine ruins of Mystras on the slopes of the Taygetus Mountains. Even a leisurely stroll along the waterfront reveals much about everyday Greek life. Here, tourism complements rather than overwhelms local culture, creating a refreshing sense of place. (For more on cruising these waters, see our guide to cruising through Greece.)
Monemvasia: The Gibraltar of the East
Rising dramatically from the sea, the massive rock island of Monemvasia looks almost mythical from a distance. A narrow causeway links it to the mainland, and its nickname—the Gibraltar of the East—fits one of Greece’s most extraordinary historic settlements.
Behind ancient stone walls lies a beautifully preserved medieval town. Narrow pathways weave among Byzantine churches, stone houses, and hidden courtyards. Monemvasia bans cars, so visitors experience the settlement much as it existed centuries ago, and every turn reveals a new architectural detail, a hidden archway, or a panoramic view over the sea.
We watched in awe as construction workers piled stone bricks on the backs of donkeys and hauled them uphill. They dug out rock patiently and carefully without excavation equipment—just shovels—to make way for more homes, and it struck us as funny to see real estate signage amid such an ancient-feeling landscape.
Monemvasia rewards curiosity and encourages unhurried wandering, which we savored until it was time to return to the yacht and head for our final destination: Athens.
Why Small-Ship Sailing Still Wins in the Mediterranean
From the cliffside villages of the Amalfi Coast to the medieval splendor of Monemvasia, each port played its own character in our story. Yet the yacht itself became an integral part of the experience, serving not just as transportation but as a lens through which we could appreciate the Mediterranean more fully.
Watching the coastline emerge on the horizon each morning, feeling the wind fill the sails, and arriving directly in the heart of historic harbors reminded us that the journey can and should be every bit as memorable as the destination. For travelers seeking a more intimate way to experience the Mediterranean, a voyage aboard Wind Spirit offers exactly that—a return to the legendary romance of the sea.
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