Cruise to Explore Southern Italy and The Dalmatian Coast with This 8-Day Itinerary

Lose yourself in Venice’s labyrinth of winding alleys and consider a romantic gondola ride through the canals—or simply enjoy the sounds of gondoliers serenading their passengers before departing from the heart of the city. Windstar’s small ships are among the only ones still permitted to sail from the city center. As Wind Surf sets off, its seven sails unfurl accompanied by Vangelis’ rousing anthem Conquest of Paradise, a beloved Windstar tradition. Although Wind Surf is the world’s largest sailing vessel, it hosts just 342 guests so you can enjoy its relaxed atmosphere and the opportunity to slip into small ports that larger ships can’t access.

If you’d like to spend more time in Italy, consider a Cruise Tour pairing your Windstar voyage with an overland excursion to Lake Como where you’ll visit the Villa Carlotta for a garden tour and wine tasting and take a scenic cruise on the lake. Then, return to Venice where you’ll spend one night in a luxury hotel and enjoy a guided tour of St. Mark’s Square and the iconic Rialto Bridge.

Rovinj, a picturesque fishing port on Croatia’s Istrian peninsula, called “Croatian Tuscany” thanks to its fortified hilltop towns, olive groves, and vineyards, is only accessible to small ships. Revel in its beguiling maze of cobblestone streets and stunning collection of Romanesque, Gothic, and Renaissance buildings.

An excursion to Porec includes tours of the 6th-century Euphrasian Basilica and the ancient remains of two Roman temples, followed by a wine tasting in the cellar of one of Croatia’s best-known winemakers. Alternatively, board an inflatable boat to explore Rovinj’s islands and Lim Fjord, one of the most beautiful fjords outside Norway. Istria is known for white truffles, olive oil, wine, and oysters (Anthony Bourdain was a fan), so consider stopping in a rustic konoba (tavern) for a lunch of truffle pasta.

The spectacular 1,700-year-old Diocletian Palace, a UNESCO World Heritage Site and one of the best-preserved examples of Roman architecture in the world, dominates Split’s Old Town. Built as a home for the Roman emperor Diocletian at the turn of the 4th century, the palace is noted for its elaborate Golden Gate and the Cathedral of St. Duje, the world’s oldest Catholic cathedral still in use in its original structure. Parts of Game of Thrones were filmed in its underground passageways. Visitors can climb 200 steps to the top of the Romanesque bell tower for a stunning panorama of the city and its surrounding islands.

Central to local life, Split’s outdoor market, Pazar, lets you experience the city’s true local spirit. Stroll what’s considered the “living room” of Split, the Riva, a promenade that dates to the reign of Napoleon, and relax on the central Bacvice Beach within walking distance from the pier.

For an adventure, take a thrilling inflatable boat ride to the medieval gem of Trogir, known for its magnificent 13th-century Cathedral of St. Lawrence, followed by an afternoon at a secluded pebble beach where you’ll enjoy swimming in crystal-clear water. Foodies will want to join the culinary excursion to a local market where they’ll accompany a chef to pick up organic ingredients and then prepare a feast accompanied by fine Croatian wines. Or visit the serenely beautiful Krka National Park, known for its majestic waterfalls.

Dubrovnik’s prized location overlooks the stunningly blue Adriatic Sea and its beautifully preserved gothic, Renaissance, and baroque churches, monasteries, and palaces. Windstar docks right outside the famous walls of the city (unlike most cruise lines that dock further away). Walk along the marble cobblestone streets and city walls and if you’re a Game of Thrones fan—you’ll recognize Pile Gate where King Joffrey was attacked by an angry mob; Lovrijenac Fort which served as The Red Keep castle; and the Jesuit Staircase where Cersei Lannister walked naked through the streets.

Croatia makes wonderful wines, and you’ll have the opportunity to enjoy a tasting of top-rated vintages led by third-generation winemaker Andro Crvik at his vineyard in the picturesque village of Komaji. Or visit the Novakovic Family Village Estate in the charming village of Cilipi where the family has been producing brandy, wine, and olive oil for generations. Niko Novakovic will prepare a delicious meal featuring prsut (smoked ham) accompanied by local cheese and freshly baked bread. The star of the meal is peka, a traditional stew of veal, potatoes, and herbs cooked over hot coals.

To appreciate Dubrovnik from the water, consider a kayak excursion to Lokrum Island where you’ll explore the remains of a 12th-century Benedictine monastery and enjoy a picnic lunch on the beach before paddling back to your yacht—or spend the night on the town with plenty of time to explore.

Montenegro’s stunning bay, surrounded by dramatic cliffs, looks like a slice of Norway dropped on the Balkan coast. Although not technically a fjord (it wasn’t formed by glaciers), the narrow body of water is nonetheless incredible and often called Europe’s southernmost fjord. One of the best ways to appreciate Kotor’s natural beauty is to take a speed boat ride across the sparkling Bay of Kotor to the Blue Cave where the reflection of the sun turns the water a luminescent cobalt blue.

An important artistic and commercial center in the Middle Ages, today Kotor is known for its picturesque Old Town (in walking distance of the pier), four Romanesque churches, and fortified city walls. The city has an Italianate feel as many of the Old Town’s structures were built by the Venetians between the 15th and 18th centuries and the main square is dotted with outdoor cafes. For hardy hikers, the panoramic view from St. John’s Fortress, an ascent of roughly 4,000 feet, is spectacular. Hike the wall to summit St. John Mountain where you can see equally stunning vistas of the bay from the Church of Our Lady of the Remedy.

A short drive from Kotor lies the seaside village of Perast where you’ll explore local churches before taking a private boat to Our Lady of the Rocks, a 17th-century church built on a small manmade island and best known for 68 stunning wall paintings by Tripo Kokolja, a local Baroque artist. Gourmands will want to visit the Moric Family home where the family produces the region’s only organic olive oil. After a short presentation by Ilija Moric, President of Montenegro Olive Oil Producers Association, enjoy a buffet lunch including locally smoked ham, bacon, sausages, homemade cheese, salad, and apple pie.

After departing Kotor, enjoy a day at sea where you can have a soothing massage in the new World Spa by Windstar or work out in the Fitness Center before settling into a lounge chair by the pool with a good book.

With its panoramic views of the glittering Ionian Sea and majestic Mount Etna, it’s no wonder that the small hilltop town of Taormina is known as “The Pearl of the Ionian Sea.” Its famous theater, Teatro Antico di Taormina, was built by the Greeks in the 3rd century B.C.E. and modified a century later by the Romans who had conquered Taormina. It’s known for flawless acoustics as well as its stunning views of the sea and Mount Etna. Fans of the second season of The White Lotus will recognize the theater as the place Albie took his father, grandfather, and Portia.

Taormina is best explored on foot as many of its streets are closed to traffic. Piazza IX Aprile, a panoramic terrace lined with Baroque churches and faded pink buildings, is the town’s loveliest square and locals often enjoy their evening passeggiata (stroll) here.

Godfather fans will want to take the “In Godfather’s Steps” excursion which visits the village of Savoca and Bar Vitelli, where in The Godfather I, Michael Corleone asked for the hand of Apollonia Vitelli and the Church of San Nicolò where the wedding took place. Forza d’Agro, which stood in for the town of Corleone in The Godfather II and III, is home to Cathedral St. Annunziata, which appeared in several scenes.

Mount Etna is famous for its volcanic wines and wine lovers shouldn’t miss an excursion to the family-owned Gambino Winery located on the eastern side of Mount Etna at 2,625 above sea level. Enjoy a wine tasting paired with local cheeses, olive oil, and other Sicilian specialties on the winery’s sunny terrace with fantastic views.

Sorrento has magnificent views (and sunsets) over the Bay of Naples and Mount Vesuvius, lovely shops and galleries, and easy access to the archaeological sites of Pompeii, Herculaneum, and Torre Annunziata, and the former fishing village of Positano.

Take a guided tour of Sorrento, stopping to admire the Romanesque cathedral with its marble bell tower and delicately crafted wooden inlay choir. Inlaid woodwork is a typical craft of Sorrento and makes an excellent gift (as does a bottle of locally made limoncello). Sorrento’s main square, Piazza Tasso, is named for a 16th-century poet and its fashionable Fauno Bar is a popular place to stop for an aperitivo.

The ruins of Pompeii and its inhabitants have been perfectly preserved since the eruption of Mt. Vesuvius in 79 C.E. On an optional excursion, you can explore the UNESCO World Heritage Site’s highlights including the world’s oldest surviving amphitheater, which was built in 70 B.C.E. and capable of holding up to 12,000 spectators; the Villa of Mysteries and its three remarkably preserved frescoes depicting the mysteries of Dionysus; and the House of Faun, one of the largest homes in Pompeii which shows how the elite lived. If you’re interested in the better-preserved remains of Herculaneum or the well-preserved frescoes of the Villa Oplontis in Torre Annunziata, consider booking a private tour.

For a distinctive view of the region’s stunning scenery, head down to the Watersports Platform to check out a kayak or a stand-up paddle board and explore the surrounding waters.

Positano, the site of white, pink, and yellow houses clinging to the hillside and the clear turquoise waters of the Tyrrhenian Sea, has attracted many authors, artists, and bold-face names including Steinbeck, Picasso, Leonard Bernstein, and Jackie Onassis. Visit the Church of Santa Maria Assunta with its colorful Majolica-tiled dome and 13th-century Byzantine icon of the Black Madonna and Child, which was said to have been smuggled by pirates. The main street, Viale Pasitea, is named for the goddess of rest, relaxation, and meditation, so where better to kick back in a cafe with a Sorrento spritz (made with limoncello and prosecco) and enjoy the view.

Your cruise ends in magnificent Rome but that doesn’t have to be the end of your Windstar vacation. Consider a two-day pre- or post-tour as part of a Cruise Tour which includes tours of the ancient Colosseum completed in 80 C.E., the gold-painted ceilings and shimmering mosaic walls of the Basilica of San Clemente, and the Vatican Museum and its Sistine Chapel where you’ll gaze in awe at Michelangelo’s masterpiece, Last Judgment. Two nights in a hotel will give you ample time to explore Rome on your own and enjoy some delicious Roman delicacies before returning home.