Arrive in Rome and transfer to the Pantheon Iconic Hotel Roma, your stylish retreat in the heart of the Eternal City. Tonight, begin your journey with a short walk to the 16th-century church of San Luigi dei Francesi for an exclusive, after-hours visit to the Contarelli Chapel. In the quiet of the evening, experience Caravaggio's complete St. Matthew cycle – considered a masterpiece for its dramatic storytelling – revealed in an intimate setting few travelers witness.

Today your adventures veer away from the typical tourist route as you taste your way through Trastevere, a neighborhood full of family-run trattorias, ivy-draped lanes, and quietly beautiful churches and artisan shops. Join a walking tour with a series of delicious food stops. This afternoon, you'll transfer to the pier to board Windstar's Star Legend for the next leg of your journey.

YOUR CHOICE
Enjoy a morning to yourself in Rome to wander at your own pace or linger in a café before rejoining the group for your embarkation.

Enjoy a full day at sea aboard Windstar's Star Legend, where ocean time is part of the experience. Settle into the ship's rhythm – wide-open views from the deck, on-deck hot tubs, and the luxury of "nothing on the calendar" time. Savor the ship, rejuvenate, and let the rest of the journey come to you.

YOUR CHOICE
Make the day your own at sea. If you're in the mood to be pampered, schedule a spa treatment, then delight over the ship's complimentary food and beverages – whether it's a midafternoon bite or a cocktail with a sunset on the side.

Begin your morning by boarding a private boat at Marina Corta for a scenic cruise along the coast of Lipari. Glide past the island's striking quarry before a refreshing swim in crystal-clear water. Continue by sea past another seaside village en route to Salina – known as the most breathtaking Aeolian Island – for a second swim stop. You'll encounter a dramatic amphitheater of cliffs and sea when you reach the Bay of Pollara. Before returning to the ship, you'll enjoy lunch and granitas in Lingua.

YOUR CHOICE
Cruise the Aeolian Islands by private boat, passing coastal villages and swim-worthy coves, or spend time on your own in Lipari – known for its volcanoes and mythological roots.

Set out in a vintage Fiat 500 to ride past and stop at Palermo's iconic landmarks. Your morning continues with a private visit to the Majolica Museum, home to more than 5,000 beautifully hand-painted majolica tiles. In the evening, you'll step into the grandeur of palazzo Francavilla for a private tour followed by a special dinner celebrating the well-preserved aristocratic atmosphere.

YOUR CHOICE
Free time to explore Palermo as you please.

Defined by its authentic Italian landscape, and dreamlike vineyards, Trapani stands out as a coastal countryside escape within Sicily. Today, you'll transfer to 4x4 buggies for an adventurous ride through the lush countryside. Stops will be made along the way, so you can spot the various crops, pick some of your favorite fruit directly from the trees, and enjoy a wine tasting of the region's specialties. 

YOUR CHOICE
An afternoon at leisure in Trapani to soak in the seaside town center, visit the historic Clock Tower, and taste some of their famous African-inspired cuisine or spend time on the Star Legend to rejuvenate and relax.

After waking up to the sea breezes of Porto Empedocle, you'll soak up Sicily's most captivating contrasts – ancient wonders and the peaceful countryside. 

YOUR CHOICE
A day in the archeological ruins of the Valley of the Temples, featuring a private villa visit and a hands-on cooking class, or a guided e-bike ride with stops at idyllic farms, including a private lunch at a countryside home.

Today you'll wake up not only in a new city, but an entirely new country. Begin in Mdina, where a guided walking tour reveals quiet streets shared by pedestrians and horse-drawn carriages instead of cars. Then continue to a renowned boutique winery for a tasting and a closer look at the captivating Maltese vineyards.

YOUR CHOICE
An afternoon spent in Valletta, where the color blue sneaks through in every detail and the ocean breeze surrounds every corner. You can explore the Upper and Lower Barrakka gardens, St. John's Co-Cathedral, and the scenic overlooks in Malta's vibrant capital city, or you may choose to spend leisure time on the ship.

After sailing back to Sicily, you'll find yourself at a local farm where you'll be introduced to your truffle hunting guides –the talented truffle dogs – that will lead your hunt for the elusive edible treasure. You'll then meet the farm owner who will demonstrate how to produce ricotta, mozzarella, and tuma cheeses from fresh milk. After an exciting day centered around food, enjoy a well-earned Sicilian lunch, featuring wine, cheese, and other specialties. 

YOUR CHOICE
Explore the town of Ortigia, either on your own or with your Roam Director, or head back to your ship for an afternoon of relaxation.

Today centers on Europe's most active volcano – Mt. Etna. Discover its rugged slopes from new perspectives, whether you hike across its terrain or decide to enjoy Italian wines with all-encompassing views of the volcano.

YOUR CHOICE
Alongside a mountaineering guide, take in the majesty of Mt. Etna as you ride and climb its slopes. You'll stop at scenic overlooks, hike to craters to learn about past eruptions, and visit a lava cave where an entire hotel was once buried under lava flows. For those who prefer a more classic Italian day, you'll head to Taormina for a walking tour of the enchanting cliff-top village before a guided tasting and farm-to-table lunch on the slopes of Mt. Etna – 2,200 feet above sea level.

After arriving in Sorrento, journey to the remarkably preserved ruins of Pompeii, where daily life was frozen in time. You'll get special behind-the-scenes access to recently uncovered frescoes and architectural details rarely viewed by visitors. An expert archaeologist will provide insight and context to every marvel you come across.

YOUR CHOICE
Join your Roam Director for a guided walk through Sorrento – exploring its tucked-away lanes, local shops, and coastal views – followed by free time to stroll and shop as you wish. Or return to the ship for a relaxed afternoon onboard.

As your ship sails to Civitavecchia, you'll enjoy a final breakfast before departing. Transfers are included to Rome's Leonardo Da-Vinci Fiumicino Airport (FCO).

YOUR CHOICE
Morning departures or extend your stay in Italy.