If you’re dreaming of a luxury small-ship cruise through Italy, Croatia, and Montenegro, the Windstar Cruises Italy Classics & Dalmatian Coast itinerary is one of the most unforgettable ways to explore the Mediterranean. This incredible 9-day voyage blends ancient history, stunning coastlines, UNESCO World Heritage Sites, and charming old towns—all while enjoying Windstar’s signature yacht-style cruising experience.
In this post, I’ll walk you through each stop on this spectacular itinerary, including insider tips, must-see attractions, and insights for planning your own Mediterranean cruise adventure.
Why Choose Windstar Cruises for the Italy Classics & Dalmatian Coast Itinerary?
Windstar is known for intimate, small-ship cruising—meaning you get access to ports larger ships cannot reach, along with personalized service, gourmet dining, and a relaxed, yacht-like atmosphere. This itinerary is perfect for travelers who want:
- Authentic Mediterranean destinations
- Historic old towns and UNESCO sites
- Stunning beaches, medieval architecture, and coastal scenery
- Fewer crowds and a more boutique cruise experience
Whether you’re a first-time cruiser or a seasoned explorer, this route highlights the best of Italy, Croatia, and Montenegro.
Day-by-Day Breakdown of the Windstar Italy Classics & Dalmatian Coast Cruise
Day 1: Departure from Venice, Italy
Your journey begins in Venice, a city that needs no introduction. Its iconic canals, Gothic palaces, and centuries-old bridges set the tone for a magical Mediterranean cruise.
Top things to do in Venice before embarkation:
- Wander through St. Mark’s Square and tour the Basilica
- Take a classic gondola ride through the canals
- Explore the Doge’s Palace and Bridge of Sighs
- Enjoy cicchetti and Prosecco in a canal-side bacaro
Day 2: Rovinj, Croatia – A Hidden Gem of the Istrian Coast
Your first port of call is Rovinj, a fairytale-like fishing village on the Istrian Peninsula. This colorful harbor town is one of Croatia’s most romantic and scenic destinations.
What makes Rovinj special?
- Venetian-style old town with narrow stone streets
- The hilltop Church of St. Euphemia
- Boutique shops and seaside cafés
- Crystal-clear Adriatic waters perfect for swimming
Must-do activities:
- Climb the bell tower for panoramic views
- Explore the artist district of Grisia Street
- Try truffle-infused Istrian cuisine
Day 3: Split, Croatia – Roman History Meets Coastal Beauty
Next, your Windstar yacht sails into Split, home to one of the world’s most impressive Roman ruins: Diocletian’s Palace. This living UNESCO World Heritage Site is a city within a city, filled with cafés, markets, and ancient passageways.
Highlights of Split:
- Walking tour of Diocletian’s Palace
- The atmospheric Peristyle Square
- Climbing Marjan Hill for sunset views
- Fresh seafood at the waterfront Riva promenade
Don’t miss: Wandering the palace basements featured in Game of Thrones filming locations.
Day 4: Dubrovnik, Croatia – The Pearl of the Adriatic
A Mediterranean cruise wouldn’t be complete without Dubrovnik, one of the most breathtaking walled cities in the world.
Top experiences in Dubrovnik:
- Walk the city walls for jaw-dropping coastal views
- Take the cable car to Mount Srđ
- Explore the charming Old Town and Pile Gate
- Swim in the Adriatic near Banje Beach
Windstar often tends to anchor offshore, giving you beautiful views of Dubrovnik’s orange-tiled rooftops as you tender in.
Day 5: Kotor, Montenegro – A Dramatic Fjord and Medieval Wonder
Prepare for one of the most scenic sail-ins of your life: entering the Bay of Kotor, often called Europe’s southernmost fjord.
Why Kotor is a favorite among cruisers:
- It’s a UNESCO World Heritage Site
- The bay is surrounded by steep mountains and mirror-calm water
- The old town is a medieval maze of cobblestone streets
Top things to do:
- Hike the Fortress of St. John for panoramic views (1,300+ steps!)
- Explore Kotor’s cat museum—yes, really
- Visit the seaside village of Perast and Our Lady of the Rocks
Day 6: Day at Sea – Relaxation and Yacht-Style Cruising
Windstar’s day at sea is pure luxury. This is when you really feel the difference between a traditional mega-ship and a small-yacht experience.
What to enjoy onboard:
- Poolside lounging
- Wine tastings or cooking classes
- Spa treatments
- Outdoor dining under the sails
Day 7: Taormina, Sicily – Volcano Views and Ancient Ruins
Your next stop is Taormina, a glamorous clifftop town overlooking the Ionian Sea with Mt. Etna rising in the distance.
Top things to do in Taormina:
- Visit the Ancient Greek Theatre (Teatro Antico di Taormina)
- Stroll Corso Umberto for gelato and shopping
- Take the cable car down to beach clubs at Mazzarò
- Enjoy Sicilian food and local wines
Day 8: Sorrento, Italy – Gateway to Positano and the Amalfi Coast
Sorrento is one of the highlights of the Windstar Italy cruise, offering access to the stunning Amalfi Coast. You visited Positano, one of Italy’s most famous cliffside towns—and absolutely worth the trip.
Sorrento Highlights
- Lemon groves and limoncello tastings
- Beautiful views of the Bay of Naples
- Charming old town full of artisan shops
What to do in Positano
- Wander the colorful, steep streets
- Relax on Spiaggia Grande
- Shop for handmade sandals and ceramics
- Enjoy an Aperol spritz with sea views
Day 9: Arrival in Rome – The Eternal City
Your cruise ends in Rome (Civitavecchia), but the adventure doesn’t stop. Rome is one of the most historic and culturally rich cities in the world.
Top post-cruise activities:
- Tour the Colosseum and Roman Forum
- Visit St. Peter’s Basilica and the Vatican Museums
- Toss a coin in Trevi Fountain
- Relax with a final Italian espresso or gelato
Final Thoughts: Why This Is One of Windstar’s Best Mediterranean Cruises
The Windstar Italy Classics & Dalmatian Coast itinerary combines everything travelers love about the Mediterranean: charming old towns, breathtaking coastlines, rich history, world-class cuisine, and ports you simply can’t reach on larger cruise ships.
From Venice’s canals to Dubrovnik’s city walls, from the fjords of Montenegro to the pastel beauty of Positano, this cruise delivers unforgettable experiences every single day.
If you’re looking for a luxury small-ship Mediterranean cruise with diverse destinations and smooth sailing, this itinerary is one of the best you’ll find.
For more cruise inspiration, check my post here: Windstar Cruise in Mediterranean – Annytravels
Your sincerely,
Anny
