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Cruise Europe | Windstar's Enchanting Greece and the Amalfi Coast

Sample Itinerary


Europe, Greece, Italy

Trip Duration

7 nights / 8 days

From the ancient history of Rome and charming towns along the Amalfi Coast in Italy to the Mediterranean mystique of Gythion and Athens, Greece, Greece, enjoy enchanting ports aboard the luxurious Star Legend sailing yacht. Below is just a sample of the immersive itineraries our Destination Specialists can create. Click on the experiences links in the itinerary to see other curated excursion choices offered by Journese. Our Destination Specialists are happy to book our hotels and excursions highlighted in the itinerary below or let them know if you would like something customized. And, feel free to offer our non-hyperlinked suggestions to your clients to further explore the destination.


Day 1: Rome, Italy/Embarkation |

Your enchanting voyage begins in Rome with pre-cruise shopping or sightseeing, exploring everything from St. Peter's Basilica and the Vatican to the Colosseum, Pantheon, museums, artwork and every historic corner of this ancient city. Then, in mid-afternoon, board the sleek, Star Pride yacht for your once-in-a-lifetime cruise. Known as the essence of small ship sailing, delight in open teak decks, gourmet dining and luxurious staterooms with ocean views, marble baths and fine Egyptian linens, plus amenities including WindSpa, a watersports platform, casino, a lounge with live music and dancing, library, pool and hot tub. Settle into your well-appointed stateroom and prepare to set sail.

Depart from Rome on the Tyrrhenian Sea as you get underway to your first port along the western coast of Italy. Gather with your new yachting friends for a welcoming toast and dining experience in AmphorA, with a course-by-course offering, crafted to highlight the spectacular flavors of the regional cuisine and served with a selection of vintage wines.

Day 2: Sorrento, Italy |

Begin your day with breakfast alfresco, buffet-style or full-service dining in Veranda onboard before you cruise into port in Sorrento. Disembark on a variety of optional excursions to areas of Pompei, Torre Annunziata or Herculaneum, where you can gain insight into the lives of the ancient Romans with the exploration of well-preserved ruins and ancient properties, mosaics, paintings and pathways. Or, choose to ride a private motorboat to explore the coast of Positano, with its white Moorish-style houses, luxurious gardens, and unique shops and cafes, for a half-day of inspiring discovery.

This evening, sip a pre-dinner cocktail and reminisce about your experiences in lovely Sorrento. Then, dine under the stars at Candles, Windstar's signature restaurant on deck, transformed into an oceanic paradise filled with tantalizing offerings and paired with the perfect varietal.

Day 3: Lipari, Italy |

Following a leisurely breakfast this morning, get ready to dock at Liparai, the largest of seven Aeolian Islands. Experience the island's natural beauty with a panoramic excursion including stops at the best viewpoints and a visit to Canneto Village. Or try your hand at making your own pizza in a traditional Sicilian pizzeria, then partake, accompanied by wine and Aeolian cookies. For adventure seekers, embark on a boat excursion around the island and a guided hike ascending the volcano. For those who wish to relax, you can enjoy the geothermal mud baths or stay along the beach before returning to the yacht.

Relax onboard tonight with a sumptuous made-to-order dining experience and follow the stars in the sky as you move ahead to your next port.

Days 4 - 5: Giardini Naxos, Italy/At Sea |

Just as you are sipping your favorite cup of cappuccino this morning, the ship arrives in Sicily. Explore this remarkable Italian island at your leisure with a private vehicle, driver and English-speaking guide, designing your own itinerary ashore and creating your own personal stops. Spend time in Taormina, a popular cliff side town built in the 3rd-century B.C., exploring the iconic Greek Theater and the charming streets of the city with its cafes, shops and restaurants. Or venture south toward Catania to find the most active volcano in Europe, Mount Etna, for a picturesque view of this incredible landmark.

The following day is at sea. Soak up the sun on a deck chair with a book, indulge in a pampering spa treatment, take a refreshing swim in the pool or test your luck at the casino as you sail to your next port in Greece.

Day 6: Gythion, Greece |

Following a sumptuous breakfast buffet, get ready to celebrate everything Greek. Lighthearted sculptures welcome you to this exuberant port brimming with pastel houses and whitewashed laneways, friendly shops, coffee houses and waterfront cafes, ideal for your first cup of rich coffee or glass of ouzo. Take an optional excursion to the Dyros Caves, cross the orange and olive groves of Laconia to Taygetus Mountain on your way to the medieval town of Mystras, or customize your own itinerary ashore with a private car, driver and English-speaking guide.

After another amazing Windstar day, celebrate this remarkable voyage with a spectacular deck barbecue. The attentive crew will serve a spectacular meal prepared from fresh local ingredients and accompanied by their own special brand of entertainment for an evening of entertainment under the twinkling stars.

Day 7: Monemvasia, Greece |

Your luxury yacht arrives in port as you savor a delectable breakfast in your private stateroom or buffet offering at Veranda. Spend the day exploring the unique Castle Town of Monemvasia, carved and built entirely on the backside of a sea rock, making it invisible to the mainland. Whether by foot, or by private car with an English-speaking guide, experience the romance and mystery of this hidden Greek gem. Discover narrow laneways, an ancient cathedral, Byzantine churches and ruins, quaint villages and picturesque shops, together with its natural beauty and stunning beaches for an unforgettable day.

For a magical onboard finale, intrigue your senses with eclectic flavors and engaging aromas with an exquisite dinner under the stars at Candles. Gaze at the sunset over the ocean as you raise a glass of ouzo to your partner and toast to your final evening aboard your luxury yacht cruise.

Day 8: Athens, Greece/Departures |

Awaken in the brightest jewel of the Mediterranean and birthplace of civilization - Athens, Greece. Experience this remarkable ancient capital city by private car with an English-speaking guide or on your own. Be amazed at the countless ruins and modern structures including the Parthenon and the Acropolis as you witness the historical evolution in this enchanting city.

Following your day of excursions, head to your post-cruise hotel or to the airport for your homebound flight. Bid a fond farewell to beautiful Greece as you make plans for your next luxurious Windstar Cruise. And remember, with many options across Greece, peruse Journese elite portfolio for the ideal post-cruise resort stay and many activity and excursion options.

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