21-Day Around Italy's Boot: Greek Isles & Venice Overnight Cruise

Day 1 - Venice (Trieste)

Arrive: Sat 18 November 2028

Trieste is the capital city of the Friuli Venezia Giulia region in northeast Italy. A port city, it occupies a thin strip of land between the Adriatic coast and Slovenia’s border on the limestone-dominated Karst Plateau. Italian, Austro-Hungarian and Slovenian influences are all evident in its layout, which encompasses a medieval old city and a neoclassical Austrian quarter.

Day 2 - Venice (Trieste)

Depart: Sun 19 November 2028 at 21:00

Trieste is the capital city of the Friuli Venezia Giulia region in northeast Italy. A port city, it occupies a thin strip of land between the Adriatic coast and Slovenia’s border on the limestone-dominated Karst Plateau. Italian, Austro-Hungarian and Slovenian influences are all evident in its layout, which encompasses a medieval old city and a neoclassical Austrian quarter.

Day 3 - At Sea

Day 4 - Dubrovnik

Arrive: Tue 21 November 2028 at 08:00 / Depart: Tue 21 November 2028 at 23:00

On the southern end of Croatia's Adriatic coast, Dubrovnik staked its claim to glory during the 450 years it existed as the independent Ragusan Republic, shoulder to shoulder with mighty forces like Venice and the Ottoman Empire. Once a renowned seafaring, shipbuilding and trading center, today it's an enchanting tourist destination. Dubrovnik seduces sightseeing visitors with its polished (and very clean!) limestone streets, theatrical architecture, charming café, welcoming restaurants and distinctive shops along scenic side streets. The natural backdrop, much of which is protected, consists of pine and cypress forests and the shimmering Adriatic, dotted with uninhabited islands. Visitors quickly discover that the wider Dubrovnik area is just as striking as its main attraction—the Old Town. A wander around the historic heart of Dubrovnik can hit the main sights, but take it a step further (or a staircase further, really), and you'll see that people do still live in the historic quarter, even though its polished streets make it look like a museum. You may catch the sound of a piano from the High School of Music and Arts, or hear the Dubrovnik Symphony Orchestra rehearsing in the Revelin Fortress, or encounter school kids on a break. Life unrolls as you stroll past.

Day 5 - Kotor

Arrive: Wed 22 November 2028 at 08:00 / Depart: Wed 22 November 2028 at 17:00

Kotor is located along one of Montenegro's most beautiful bays. First settled during the days of ancient Rome, the city today has a well preserved urban centre with a vibrant community. Medieval architecture and numerous monuments of cultural heritage have made Kotor a UNESCO listed “World Natural and Historical Heritage Site."

Day 6 - Corfu

Arrive: Thu 23 November 2028 at 08:00 / Depart: Thu 23 November 2028 at 17:00

Fortresses flank your entrance to this most beautiful of the Ionians. Lose yourself in the Venetian old town or head north for dramatic seascapes. Sample shore excursion: Achillion Palace & Private Villa.

Day 7 - At Sea

Day 8 - Athens

Arrive: Sat 25 November 2028 at 07:00 / Depart: Sat 25 November 2028 at 16:00

No modern metropolis is more steeped in myth than Athens, Greece. From the gritty port of Piraeus—gateway to Greece’s fabled isles—to the Parthenon—eternal symbol of Western civilization—Athens has attracted adventurers and classicists for centuries. This heritage is still very much alive for modern visitors sightseeing in Athens: ancient stadiums and temples dwell alongside apartment blocks, modern performances are staged in the marble amphitheaters where Greek drama was born and millennia-old monuments are scattered in the archaeological park that circles the Acropolis. One of the world’s oldest maritime powers, Athens is blessed with a balmy climate and stunning coastline. The seaside suburbs of Athens are scalloped with sandy beaches, fancy yacht clubs and glamorous beach bars. While the Athenian lifestyle is known for late-night dinners and dancing until dawn, the city shines brightly by day in the bustling markets, lively cafés and fascinating museums that illuminate Greece's past and present. Contemplate the magnitude of all that culture and ancient tourist attractions while marveling at the sun setting into the Aegean or rising over the Acropolis.

Day 9 - Santorini

Arrive: Sun 26 November 2028 at 08:00 / Depart: Sun 26 November 2028 at 18:00

Your harbor on this island was created by a volcano in 1500 BC., and the effect is still explosive: steep cliffs rise from sea level, cubist white houses glow in the Aegean sun. Sample shore excursion: Panoramic Santor ni.

Day 10 - Mykonos

Arrive: Mon 27 November 2028 at 08:00 / Depart: Mon 27 November 2028 at 17:00

Informality rules on this sunny isle where pleasure-seekers from around the world come to play. Ramble along narrow streets past white-washed houses and blue-domed churches, bouganvillea-covered walls and thread-like, step-laden footpaths leading everywhere.

Day 11 - Kusadasi

Arrive: Tue 28 November 2028 at 08:00 / Depart: Tue 28 November 2028 at 23:00

Kusadasi in Turkey is the gateway to one of the most legendary cities of the ancient world: Ephesus. St. Paul preached in its Great Theater, while the facade of the Celsus Library survives as a testament to the city’s role as a center of learning and culture. Not far from Ephesus, the Temple of Artemis (also known as the Temple of Diana), one of the Seven Wonders of the ancient world, once stood, drawing pilgrims from around the Mediterranean. While it no longer stands, it is possible to walk amongst its foundations and the remains of its towering columns. Other historic sites can also be found nearby: The House of Mary is believed to be the home of Jesus’s mother at the end of her life, and the Basilica of St. John, constructed in the 6th century, marks the location of his tomb. (Like Mary, he spent his final years in Ephesus.) Nearby, the Selcuk fortress reflects the period of Byzantine and Ottoman control of the region. From ancient wonders to holy sites, there are few ports in the Mediterranean as magical as Kusadasi, and a day here is a day spent in the company of some of antiquity's greatest figures.

Day 12 - At Sea

Day 13 - Thessaloniki

Arrive: Thu 30 November 2028 at 07:00 / Depart: Thu 30 November 2028 at 17:00

Thessaloniki is Greece's second major economic, industrial, commercial and political centre. Home to numerous notable Byzantine monuments and historical sites, walking through Thessaloniki is truly a journey back in time.

Day 14 - At Sea

Day 15 - Istanbul

Arrive: Sat 02 December 2028 at 07:00 / Depart: Sat 02 December 2028 at 21:00

Blurring the line between east and west, Istanbul stands at the crossroads of two continents. The city's architecture is rivalled only by its spectacular natural setting on the Bosphorus Strait. See the Blue Mosque, the Topkapi Palace and the Byzantine Church of St Sophia. Take time to wander through the Grand Bazaar or the Spice Market and sample baklava and shish kebabs.

Day 16 - At Sea

Day 17 - Mykonos

Arrive: Mon 04 December 2028 at 08:00 / Depart: Mon 04 December 2028 at 17:00

Informality rules on this sunny isle where pleasure-seekers from around the world come to play. Ramble along narrow streets past white-washed houses and blue-domed churches, bouganvillea-covered walls and thread-like, step-laden footpaths leading everywhere.

Day 18 - Chania, Crete

Arrive: Tue 05 December 2028 at 08:00 / Depart: Tue 05 December 2028 at 18:00

The port of Souda on the Aegean Sea is home to a Greek and NATO naval base and is located six kilometers (three miles) from Chania—the second-largest city on Crete, which itself is the largest of the Greek Islands. Once you’re in Chania, set your compass for the historic waterfront with its famous Venetian Harbor dating to the 14th century. Walk along the breakwater to the restored 500-year-old lighthouse for views that are particularly photogenic from late afternoon until sunset. The atmospheric tangle of streets that is Old Town is easily explored on foot, and you can stop at one of the many outdoor cafés for a bouyatsa (custard pastry) or a glass of Cretan red wine.Soúda can also be a jumping-off point for a visit to Rethymnon, located about 54 kilometers (33 miles) to the east. Shaped by centuries of invasion, namely by the Venetians and Turks, its Fortezza was built by the Venetians in the late 16th century and captured by the Ottomans in 1646. The Old Town has the same kind of architectural character as Chania, but on a smaller scale.

Day 19 - At Sea

Day 20 - Sicily

Arrive: Thu 07 December 2028 at 08:00 / Depart: Thu 07 December 2028 at 17:00

Messina's astrological clock is as much a man-made masterpiece as the road leading to Taormina, which canitlevers out of the rocky cliff face and stands on impossibly tall pylons. Leave it to the Italians to design a road that's both a thrill-ride and a feat of engineering! Once you're safely in Taormina, walk to the sublime Greco-Roman theatre that overlooks Naxos Bay and snow-capped Mt Etna, and spend some time on the Corso Umberto with a gelato firmly in hand.

Day 20 - Cruising Strait Of Messina

Day 20 - Evening passing Stromboli Volcano

Day 21 - Naples, Italy

Arrive: Fri 08 December 2028 at 08:00 / Depart: Fri 08 December 2028 at 18:00

Rising behind the wide curve of its bay with brooding Mount Vesuvius and the deep blue sea as a backdrop, Naples, Italy enjoys a magnificent natural setting. It is the third-largest city in Italy after Rome and Milan, and arguably the most colorful and seductive of them all: Splendor and squalor live side by side in 21st-century Naples, and the mix is intoxicating. Cruise to Naples, home to world-class museums and attractions. Naples has something for everyone - superb restaurants, eclectic shopping, a thriving contemporary art scene and an edgy and vibrant street life. But once you’ve had enough of the pounding traffic and jostling crowds while sightseeing in Naples, there are endless opportunities for exploration further afield. The celebrated Roman ruins of Pompeii and Herculaneum, both victims of Vesuvius’ devastating 79 C.E. eruption, lie just south of the city. Explore Naples' history or take a short ride over to the island of Capri on a Naples shore excursion. The delightful town of Sorrento and the magnificent scenery of the Amalfi Coast are also within easy reach, and the dolce vita glamour of Capri—not to mention the healing thermal waters of Ischia—are a short hydrofoil hop from the mainland. Naples cruises offer a perfect mix of cultural and natural attractions.

Day 22 - Rome

Arrive: Sat 09 December 2028 at 07:00 / Depart: Sat 09 December 2028

Your gateway to the Eternal City, Civitavecchia has served as Rome's seaport since the 13th century. The port has a long and venerable history. The emperor Trajan built a pleasure villa near the modern city, while Bernini and Michelangelo designed the harbor fortifications. Yet the Eternal City eternally beckons. The ancient capital of the Western World and the center of Christianity for nearly 2,000 years, Rome provides an inexhaustible feast. Visit the ruins of the Forum, view the splendors of the Sistine Chapel, or climb the Spanish Steps, once the heart of Rome's Bohemian Quarter. Rome has been a magnet luring the world's greatest artists, architects, and philosophers since the days of the Caesars.