Spain Cruise from Barcelona to Piraeus — 23 Days

22 nights · Spain · Departs Barcelona (Spain) · Visiting Palamos, Sanary-sur-Mer, Monte Carlo, Cannes, Portofino, Portoferraio, Porto Ercole, Civitavecchia-Rome, Sorrento, Messina, Gythion, Monemvasia, Piraeus-Athens, Kusadasi, Kavala, Thessaloniki, Volos, Skopelos Island · Aboard Windstar Cruises on the Star Legend

Windstar Cruises logo
Cruise lineWindstar Cruises
ShipStar Legend
Duration22 nights
Port calls19
Year built1992
Guests343
Cabins156
Crew190
Length159 m
Beam19 m
Cruising speed15.0 kn
  1. Day 1

    Barcelona, Spain

    Barcelona is a Mediterranean port city built on Roman foundations, with Gothic lanes and striking modernist architecture. La Rambla runs from Plaça de Catalunya towards the waterfront and the old town. Gaudí’s Sagrada Família and Park Güell show the city at its most distinctive. Set aside time for a market lunch and a walk through El Born, where medieval streets meet lively cafés. Barcelona’s beaches offer a welcome pause between visits.

  2. Day 2

    Palamos, Spain

    Palamós brings you to the heart of Spain’s Costa Brava, where a working fishing port meets a handsome old town. Its waterfront is famed for the prawns landed here, best sampled at a local table. Walk the promenade, visit the Fishing Museum, or follow coastal paths towards rocky coves and clear water. Girona and medieval villages lie inland, but Palamós rewards a slower day close to the sea.

  3. Day 3

    Sanary-sur-Mer, France

    Sanary-sur-Mer pairs a working Provençal harbor with an easygoing seaside rhythm, just west of Toulon. Colorful pointus—traditional fishing boats—line the quay, where the daily fish market brings the morning catch ashore. On Wednesdays, stalls spread through the town with produce, olives, textiles, and regional specialties. Climb to Notre-Dame-de-Pitié chapel for views over the bay and rooftops. The town also sheltered German-speaking writers in exile during the 1930s, including Thomas Mann and Bertolt Brecht.

  4. Day 4

    Monte Carlo, Monaco

    Monte Carlo makes a striking first impression, with superyachts in Port Hercule and the Alps rising behind the coast. A short walk leads to Casino Square, where Belle Époque architecture frames the famous casino and designer boutiques. For a quieter contrast, climb to Monaco-Ville for the Prince’s Palace, cathedral and views across the harbor. The principality is compact and easy to explore on foot, though its steep streets reward comfortable shoes.

  5. Day 5

    Cannes, France

    Arrive in Cannes and the Riviera’s polished glamour is immediately on show. Follow the palm-lined Croisette past Belle Époque hotels, designer boutiques and the Palais des Festivals, home of the film festival. Then climb into Le Suquet, the old quarter, for narrow lanes and views across the harbour. At Marché Forville, local produce and Provençal specialities offer a taste of everyday life. Ferries to the Lérins Islands make an easy escape to pine-scented shores.

  6. Day 6

    Portofino, Italy

    Portofino is a small Ligurian harbour, framed by green hills and pastel façades. On its crescent waterfront, fishing boats share the view with polished yachts. From the piazzetta, lanes climb to Castello Brown, a former fortress overlooking the harbour and coast. Walk on to the lighthouse at Punta del Capo, or take a boat to nearby Santa Margherita Ligure. A table by the water offers the best reason to linger.

  7. Day 7

    Portoferraio, Italy

    Portoferraio rises above Elba’s deep-blue harbor, its honey-colored walls reflecting the ambition of Cosimo I de’ Medici. Walk the steep lanes between the Medici fortresses, then visit Villa dei Mulini, Napoleon’s residence during his 1814–15 exile. Beyond the old town, clear coves and pale beaches invite a swim. Vineyards and coastal roads reward a longer stay. This is Tuscany with salt air and a storied past.

  8. Day 8

    Porto Ercole, Italy

    Porto Ercole sits on Monte Argentario, where southern Tuscany meets the Tyrrhenian Sea. Its old harbour curves beneath pastel houses, while sixteenth-century Spanish forts keep watch above the town. Walk uphill to the Rocca for views across the rooftops and water, then linger over lunch beside the boats. Nearby, the Feniglia nature reserve offers pine shade, dunes and a long sweep of sand. Caravaggio died here in 1610, adding a striking historical note to this coastal stop.

  9. Day 9

    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.

  10. Day 10

    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.

  11. Day 11

    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.

  12. Day 13

    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.

  13. Day 14

    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.

  14. 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.

  15. Day 16

    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.

  16. Day 18

    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.

  17. Day 19

    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.

  18. Day 21

    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.

  19. Day 22

    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.

  20. Day 23

    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 2, 2026
Last updated October 11, 2026
Author: J. Richard


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