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Sail in Italy and the Dazzling Dalmatian Coast
Imagine seeing Italy’s stunning coastline at its southernmost tip as intrepid seafarers did long ago. What better way to discover this glamorous country than by traveling in private yacht style? On Windstar Cruises’ flagship, Wind Surf, you’ll hug the “boot” in high style, then round the heel, and head north along the Dalmatian Coast. Serving 342 guests, Wind Surf is the world’s largest sailing luxury yacht, recently renovated to provide stylish public spaces and suites, plus a sound stage for live performances. 

It also offers top-of-the-line amenities in a casual atmosphere, all served by a crew that’s world renowned for delivering genuine and heartfelt service—all of which has made the cruise line the winner of AFAR’s Travelers’ Award for Small Ship Cruises. On this nine-day itinerary, you’ll sail to some of the world’s most beautiful and historic destinations along the sun-drenched shores of Croatia, Montenegro and Italy, while you engage with the locals and truly get to know the fascinating cultures from an insider’s point of view at every stop, thanks to curated excursions.
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    Vatican City at dusk
    Day 1
    Arrive in Rome
    Benvenuto a Roma! History buffs will adore this itinerary which starts in the city that houses the Vatican, its Sistine Chapel, and St. Peter’s Basilica, as well as to the ancient ruins of the Colosseum, Forum, and Circus Maximus. (There’s so much to see here, you may want to consider arriving a few days before your yacht departs to explore it for yourself.) 

    Take a walking tour of Trastevere; its narrow streets and asymmetrical alleyways will transport you back in time. A stroll along the River Tiber—past the stone bridge, Ponte Sisto, and pastel-hued homes—shows why glamour is in the air. You’ll quickly understand why mid-20th century filmmakers flocked to these stunning parts, then known as “Hollywood on the Tiber.” 

    By now you must be hungry. When in Rome, dine out as Romans and movie stars do: on the spicy-salty pasta all’amatriciana at the restaurant Enoteca Ferrara. Make sure to keep some change in your pocket and add your contribution to the coin bank that is the ornate Fontana di Trevi—legend has it this will ensure your return to the Eternal City.
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    Zagare Bay is one of the spectacular sights you can expect to see along the Italian coast.
    Day 2
    Sorrento
    Today it’s onward to Sorrento. Overlooking the famed, astonishing Amalfi Coast, Sorrento gives you a local’s-eye view of the aqua-hued Bay of Naples and Mount Vesuvius, the stratovolcano that famously decimated Pompeii. (Its last eruption was in 1944.) A ravishing ruin that has inspired poets and artists for centuries, Pompeii is now a fascinating archaeological destination, as is Torre Annunziata (at the foot of Vesuvius)—both are UNESCO World Heritage sites. 

    The city of Herculaneum, named for storied strongman Hercules, dates to the 4th century BC. A boat ride will take you to Positano, and another powerful playground for the imagination. Here, classical mythology comes alive. Picturesque Positano is the home of the Sirens, beautiful nymphs of legend whose otherworldly voices drove sailors to distraction and destruction on the rocks.
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    The seafront promenade of Giardini Naxos
    Day 3
    Giardini Naxos
    One of Sicily’s main attractions, the charming village of Giardini Naxos—a seaside resort since the seventies—sits on the coast of the Ionian Sea, alongside a spectacular bay. It’s easy to linger here, or take an excursion to Taormina, located in the city of Messina. 

    A tourist destination since the 1800s, Taormina boasts beautiful, serene beaches along the Ionian Sea that are accessible by highways from the North (Messina) and South (Catania), or by aerial tramway. That modern mode of transport brings visitors back to the Middle Ages, via the 13th-century Palazzo Corvaja. For an even more historic vibe, channel the drama of antiquity at the breathtaking Ancient Theater of Taormina. A 45-minute drive rewards thrill-seekers with more: Mount Etna, Europe’s largest active volcano.
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    Windstar ships embody the glamour of traveling by sea.
    Day 4
    At Sea
    Approximately 16 hours lie between Giardini Naxos and your next destination—so why not prepare yourself for sightseeing by relaxing on your way to the next port? Pampering is on the menu at the World Spa by Windstar, offering regional spa treatments with a United Nations of massage styles (Swedish, Japanese Shiatsu, Hawaiian Lomi Lomi). Après-massage, naptime will be extra restful, and tasteful—thanks to the staterooms’ dreamy, plush décor, featuring tufted headboards, Egyptian cotton linens, and Windstar’s signature bowls of flowers and fresh fruit. See you on the Dalmatian Coast!
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    Day 5
    Kotor
    Inhabited since ancient times, the Bay of Kotor is the southernmost part of the historic region of Dalmatia, now Montenegro. The views here are truly out of this world. More fabulous sights to see are in the medieval Old Town, yet another UNESCO World Heritage Site. Here, you’ll refreshingly find no automobiles to pollute the air and endanger pedestrians. Instead, witness incredible 12th-century Baroque palaces and Romanesque houses of worship. At the top of the Old Town, 280 meters above sea level, the Fortress of San Giovanni (St. John) is the ideal vantage point from which to observe the Bay of Kotor, which it was built to protect. You can see it all and more on the enlightening Kotor, Highlights of Montenegro tour.
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    The stunning stone walls of Dubrovnik
    Day 6
    Dubrovnik
    Formerly the Republic of Ragusa, this southern Croatian city—“the pearl of the Adriatic”—is a major destination for tourism, and for filmmaking. (TV viewers will recognize this dramatic landscape and can see the sights for themselves on the Game Of Thrones tour.) The city was added to the UNESCO list of World Heritage Sites in 1979. Wind Surf anchors directly behind Dubrovnik’s famous stone walls, among the Middle Ages’ great fortification systems. Once ashore, the Old Town welcomes its guests to imagine what life was like centuries ago, before the advent of motorized vehicles with no cars allowed here. An opening in the city wall leads to the well-situated Buza Bar, located at the edge of a cliff overlooking the Adriatic Sea. Culinary adventurers won’t want to miss the delicious Pantarul, a family-owned, farm-to-table restaurant opened by cookbook author Ana-Marija Bujic.
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    Cultural riches await in Split.
    Day 7
    Split
    Croatia’s second largest city and the largest in the Dalmatian region, Split was founded in the 3rd or 2nd century BC as a Greek colony. Later it became the location of an impressive landmark that still stands proudly today, Diocletian’s Palace, a UNESCO World Heritage Site in the center of town. 

    Split’s museums are extraordinary, notably the Gallery of Fine Arts, with its world-renowned collection of icons, and the Archeological Museum, the oldest in Croatia. Music thrives everywhere here, especially during summertime when the city holds its prestigious, annual Split Music Festival. About 30 minutes away is Trogir, another compelling World Heritage destination. The Split & Trogir, Croatia UNESCO World Heritage walking tour will give you an excellent, stimulating overview of this historic locale.
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    Day 8
    Rovinj
    This fishing port on the west coast of the Istrian peninsula is blessed by being bordered on three sides by the Adriatic Sea. Attractive cobblestone streets wind their way toward a hill on which stands St. Euphemia Cathedral. Its formidable steeple dominates the Rovinj skyline. 

    Don’t leave without a visit to the enthralling Bronze Age ruins of Monkodonja; lovers of the outdoors will delight in Rovinj’s laid-back beaches and the natural beauty of Lim Fjord. The Rib Boat Sea Adventure will give you an up-close experience of this breathtaking region’s coastal treasures along the Rovinj Archipelago and Lim Fjord.
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    Day 9
    Venice
    Ah, Venezia . . . the ultimate movie set come to life. This entire city and its famous Grand Canal constitute an exceedingly picturesque UNESCO World Heritage Site. Hail a gondola for a taxi and savor water transport as the bells of Torre dell’Orologio strike hourly and you pass beneath the Canal’s bridges, especially the ultra-romantic Ponte dei Sospiri (Bridge of Sighs). 

    On foot, discover the magic of the celebrated St. Mark’s Square and the majestic Cathedral. Those who appreciate true craftsmanship will thrill to join the Lagoon Orientation tour, which takes guests to the islands of Burano (where intricate lacemaking has become a fine art over the centuries) and Murano, where you’ll see firsthand the legendary glass-blowing process for which the area is justly famed. Wherever you venture here, Venice’s sublime splendor remains forever ageless, a draw for lovers young, and young at heart.