Italy Cruise from Civitavecchia to Piraeus — 15 Days

14 nights · Italy · Departs Civitavecchia-Rome (Italy) · Visiting Sorrento, Messina, Gythion, Monemvasia, Piraeus-Athens, Kusadasi, Kavala, Thessaloniki, Volos, Skopelos Island · Aboard Windstar Cruises on the Star Legend

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Star Legend
Civitavecchia Cruise Port: Shore Excursions & Expert Guide Sorrento Cruise Port: Shore Excursions & Expert Guide Messina Cruise Port: Shore Excursions & Expert Guide Gythion Cruise Port
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Cruise lineWindstar Cruises
ShipStar Legend
Duration14 nights
Port calls11
From fare$9,257 per person
Year built1992
Guests343
Cabins156
Crew190
Length159 m
Beam19 m
Cruising speed15.0 kn
  1. Day 1

    Civitavecchia-Rome, Italy

    Your ship docks at Civitavecchia, Rome’s seaport, about 50 miles northwest of the capital. Rome’s great monuments are within reach, but the port town rewards a closer look. Walk the waterfront to Forte Michelangelo, a 16th-century fortress begun under Pope Julius II; explore the old streets and market. Prefer a quieter day? The town’s seafront and nearby beaches offer an easy change of pace. Choose Rome for art and antiquity, or Civitavecchia for coastal life beyond the terminal.

  2. Day 2

    Sorrento, Italy

    Sorrento rises above the Bay of Naples, facing Mount Vesuvius across water busy with ferries. From here, ferries connect with Capri, while the town rewards a slower day among old lanes, churches, and sea-view terraces. Follow the scent of citrus to shops selling Sorrento lemons, locally made limoncello, and finely crafted marquetry. Then pause over lunch: the region’s seafood and Campanian produce are best enjoyed without hurry.

  3. Day 3

    Messina, Italy

    Messina faces Calabria across the narrow Strait of Messina, with mainland Italy visible from its waterfront. At noon, figures move across the cathedral’s clock tower, a daily spectacle best seen from the square. Nearby, Montorsoli’s 16th-century Fountain of Orion rewards a closer look. Excursions reach Taormina and Mount Etna, but Messina’s compact center also merits an unhurried walk.

  4. Day 5

    Gythion, Greece

    Gythion gives you a gentler gateway to the southern Peloponnese, where the Mani begins in stone and sea. Once Sparta’s seaport, this harbor town faces the water with neoclassical houses, fishing boats, and café-lined quays. Walk to Marathonisi, the islet linked by a causeway, or follow the coast to Mavrovouni’s long beach. From here, the Mani’s tower villages and the caves of Diros make rewarding excursions. Choose Gythion for an unhurried introduction to a rugged, less-traveled corner of Greece.

  5. Day 6

    Monemvasia, Greece

    Monemvasia rises from the sea as a sheer rock, joined to the Peloponnese by a narrow causeway. Step through its medieval gate into a stone-built town of vaulted lanes, Byzantine churches and Venetian-era mansions. Cars stay outside the lower town, leaving its steep alleys to walkers. Climb to the ruined upper fortress for wide views across the Aegean, then return for local wine and seafood.

  6. Day 7

    Piraeus-Athens, Greece

    Piraeus is Athens’ working harbour, not a resort port—and that is its appeal. From here, the capital’s ancient landmarks are within reach, while the waterfront keeps its own busy, distinctly Greek character. Visit the Archaeological Museum of Piraeus, then linger over grilled fish in Mikrolimano, a small harbour lined with tavernas. Metro connections make central Athens straightforward. Or stay near the water and watch ferries depart for the islands.

  7. Day 8

    Kusadasi, Turkey

    Kuşadası puts the Aegean within reach, with a lively waterfront and one of Turkey’s most celebrated ancient cities nearby. Ephesus lies about 20 kilometres inland, where marble avenues lead to the Library of Celsus and Great Theatre. Back in town, browse the bazaar, then follow the causeway to Pigeon Island and its historic fortress. The harbour-facing promenade offers an easy place to linger over the Aegean light.

  8. Day 10

    Kavala, Greece

    Kavala climbs from its harbor to the walled peninsula of Panagia, with Mount Symvolo behind it. Explore the old quarter’s stone lanes, the 16th-century aqueduct and Muhammad Ali’s early-19th-century Imaret. Along the waterfront, tobacco warehouses recall the trade that shaped the city. Order fresh fish, or take a regular ferry to Thasos, where beaches offer an easy island escape.

  9. Day 11

    Thessaloniki, Greece

    Thessaloniki rewards travelers who look beyond the waterfront. Greece’s second-largest city layers Roman, Byzantine and Ottoman history into a lively modern center. Walk the seafront to the White Tower, then explore Byzantine churches and monuments recognized by UNESCO. The Roman Rotunda and Arch of Galerius reveal the city’s imperial past. Make time for Ladadika’s tavernas and Modiano Market, where northern Greek flavors take the lead.

  10. Day 13

    Volos, Greece

    Volos sits at the head of the Pagasetic Gulf, with Mount Pelion rising behind the city. Its waterfront cafés and lively tsipouradika serve the local ritual of tsipouro with small plates. The Archaeological Museum displays finds from Thessaly, including rare Neolithic objects. Beyond town, Pelion villages offer stone mansions, shaded squares and mountain paths. Take the historic narrow-gauge railway through the hills, or follow the coast to clear-water beaches.

  11. Day 14

    Skopelos Island, Greece

    Skopelos arrives in layers: fishing boats at the harbour, whitewashed houses climbing the hillside, and pine-covered slopes beyond. On this Sporades island, the old town’s lanes lead to small churches, courtyards and views across the Aegean. Beyond the port, beaches and coves reward a drive; Agios Ioannis Kastri rises above the sea on a rocky headland.

  12. Day 15

    Piraeus-Athens, Greece

    Piraeus is Athens’ working harbour, not a resort port—and that is its appeal. From here, the capital’s ancient landmarks are within reach, while the waterfront keeps its own busy, distinctly Greek character. Visit the Archaeological Museum of Piraeus, then linger over grilled fish in Mikrolimano, a small harbour lined with tavernas. Metro connections make central Athens straightforward. Or stay near the water and watch ferries depart for the islands.

Star Legend Cruises

Published September 25, 2026
Last updated October 11, 2026
Author: J. Richard

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