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.
Itinerary / 9 DAYSPLAN YOUR TRIP
DAY 1Arrive in Rome
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.nd crafts.
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.
DAY 3Giardini Naxos
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.
DAY 4At Sea
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.
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.
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.