Greece Cruise from Piraeus to Miami — 22 Days

21 nights · Greece · Departs Piraeus-Athens (Greece) · Visiting Mykonos Island, Katakolon, Valletta, Messina, Naples, Civitavecchia-Rome, Palma de Mallorca, Funchal, Kings Wharf, Miami · Aboard Regent Seven Seas Cruises on the Seven Seas Grandeur

Regent Seven Seas Cruises logo
Cruise lineRegent Seven Seas Cruises
ShipSeven Seas Grandeur
Duration21 nights
Port calls11
Departures1 sailings
From fare$38,098 per person
Year built2023
Guests829
Cabins375
Crew542
Length223 m
Beam32 m
Cruising speed22.0 kn
  1. Day 1

    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.

  2. Day 2

    Mykonos Island, Greece

    Mykonos rewards an early start: whitewashed lanes, blue-domed churches and waterfront cafés are quieter before the cruise crowds arrive. In Little Venice, old captains’ houses lean over the Aegean, while the island’s windmills stand above the harbor. Beyond town, beaches range from lively Psarou to the broad sands of Elia. Take a short boat ride to Delos, where ancient sanctuaries and marble streets mark one of Greece’s great archaeological sites.

  3. Day 3

    Katakolon, Greece

    Katakolon is a compact seaside port on the western Peloponnese, with cafés and shops lining its waterfront. Most visitors come for ancient Olympia, about 35 kilometres inland and readily reached by road. There, the sanctuary, archaeological museum and ancient stadium bring the story of the Olympic Games into focus. Back in Katakolon, allow time for a stroll along the harbour before returning to your ship.

  4. Day 5

    Valletta, Malta

    Valletta makes a powerful first impression, its honey-coloured walls rising above Grand Harbour. Founded by the Knights of St John in 1566, Malta’s compact capital rewards exploration on foot. Enter St John’s Co-Cathedral for Caravaggio’s monumental paintings, then follow Republic Street to cafés, palaces and the Upper Barrakka Gardens. From the terraces, watch ferries cross the harbour and look towards the Three Cities. Allow time for steep lanes and quiet side streets.

  5. Day 6

    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.

  6. Day 7

    Naples, Italy

    Naples puts its history within reach: the port opens onto a compact city framed by Mount Vesuvius and the bay. UNESCO-listed streets lead to churches, palaces and the everyday theatre of southern Italian life. At the National Archaeological Museum, mosaics and objects from Pompeii and Herculaneum bring the Roman world sharply into focus. Stay close for Neapolitan pizza, or use Naples as a springboard to Pompeii, Herculaneum and Capri.

  7. Day 8

    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.

  8. Day 10

    Palma de Mallorca, Spain

    Palma rewards an unhurried first walk. From the waterfront, the Gothic towers of La Seu rise above the old city, a landmark shaped over centuries. Inside, soaring columns and Antoni Gaudí’s modernist contributions add a striking note. Beyond the cathedral, lanes lead to shaded courtyards, shops and cafés serving local ensaimada. For a wider view, take a taxi to Bellver Castle, whose circular form overlooks the bay.

  9. Day 13

    Funchal, Portugal

    Funchal sits in a broad, sunlit amphitheatre above Madeira’s deep Atlantic harbour. Its compact centre rewards exploration, from the Old Town’s painted doors to the cathedral’s carved cedar ceiling. Ride the cable car uphill to Monte for sweeping views, then descend through gardens or by traditional wicker toboggan. Madeira’s wines and market produce offer a taste of the island before your ship sails.

  10. Day 19

    Kings Wharf, Bermuda

    Kings Wharf puts Bermuda’s western end within easy reach, with cruise ships docking beside the historic Royal Naval Dockyard. Restored stone buildings house the National Museum of Bermuda; shops and cafés invite an easy first stroll. Explore the precinct, then take a ferry toward Hamilton or St. George’s for a broader view of island life. Or stay nearby for clear water and the maritime history that give this port its distinct character.

  11. Day 22

    Miami, USA

    Miami rewards travelers who look beyond its cruise terminals. South Beach pairs pastel Art Deco hotels with Ocean Drive; Little Havana serves Cuban coffee and music along Calle Ocho. The Pérez Art Museum Miami and nearby Design District reveal the city’s creative ambition. For a change of pace, Biscayne Bay and the Everglades place vivid natural landscapes within reach.

Seven Seas Grandeur Cruises

Published September 20, 2026
Last updated October 3, 2026
Author: J. Richard


Cruise Disclosure

Good to know: Prices are quoted per person based on double occupancy and include all applicable taxes and fees. Availability and prices can change quickly, so please continue through the booking process to confirm the latest availability and pricing before you pay.

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