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Greek Island Small Ship Cruises

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Sunset over Athens' port
from $2,500
SS 25%
EXPLORE

Delightful Dervishes

Piraeus - Istanbul - 8 Day Itinerary aboard Star Flyer
  • Discover Piraeus’ vibrant gateway
  • Explore Mykonos’ charming harbor
  • Visit Patmos’ serene monastery
  • Experience Chios’ mastic heritage
Starts / Ends
Pireaus Port / Istanbul
Activity Level
Variable
Set sail on an 8-day cruise from Piraeus to Istanbul aboard the Star Flyer. Explore iconic landmarks, vibrant islands, ancient ruins, and serene coastal towns before concluding in Istanbul's cultural splendor.
Cruise Details
0
Stroll the ancient walkways of Athens
from $5,999
Air Credit
EXPLORE

Ancient Mosaics

Athens to Naples - 9 Day Itinerary aboard World Traveller
  • Milos Sarakiniko beach views
  • Explore Ephesus ancient ruins
  • Capri Blue Grotto visit
  • Ionian Sea scenic cruising
Starts / Ends
Piraeus / Naples
Activities
Hiking
Activity Level
Variable
Sail through Greece, Turkey, and Italy starting in Athens on a 9-day cruise aboard World Traveller. Discover historic landmarks, seaside villages, and local cuisine. Enjoy shore excursions, cultural sites, and coastal scenery that define this Mediterranean adventure.
Cruise Details
0
Explore the colorful villages of Parga
from $10,795
EXPLORE

The Greek Islands, Corinth Canal & Adriatic

Athens - Dubrovnik - 11 Day Itinerary aboard Emerald Azzurra
  • Discover Lefkada Agia Mavra castle
  • Tour Parga hilltop Venetian castle
  • Walk Corfu Spianada square
  • Admire Dubrovnik stone walls
Starts / Ends
Piraeus / Dubrovnik
Activity Level
Variable
Experience an 11-day cruise through the Ionian and Adriatic seas on the Emerald Azzurra, visiting historic sites like Delphi and the castles of Lefkada. Conclude your journey in Dubrovnik, renowned for its ancient walls and stunning architecture.
Cruise Details
0
Poros, Greece
from $2,500
SS 25%
EXPLORE

Yachtsman's Paradise

Istanbul - Piraeus - 8 Day Itinerary aboard Star Flyer
  • Explore Istanbul’s dynamic blend
  • Visit Dikili’s quiet harbor
  • Wander Skopelos Town’s alleys
  • Walk Piraeus to ancient Athens
Starts / Ends
Istanbul / Piraeus
Activity Level
Variable
Embark on an 8-day cruise from Istanbul to Athens aboard the Star Flyer, exploring ancient sites like Pergamon and experiencing charming coastal towns. Conclude your journey in historic Athens, the cradle of democracy and Western philosophy.
Cruise Details
0
Enjoy the beautiful blue waters of the Mediterranean
from $18,990
EXPLORE

Adriatic, the Corinth Canal and the Greek Islands

Dubrovnik - Athens - 12 Day Itinerary aboard Emerald Kaia
  • Explore Dubrovnik’s walled Old Town
  • Wander Korcula’s medieval lanes
  • Experience Kotor’s Venetian charm
  • Uncover Corfu’s Old Town
Starts / Ends
Dubrovnik / Piraeus
Activities
Wine Tasting
Activity Level
Variable
Embark on a 12-day cruise aboard the Emerald Kaia, exploring the Adriatic, Ionian, and Aegean seas from Dubrovnik to Athens. Discover scenic landscapes, historic sites, and charming ports, including Kotor, Corfu, and Lefkada along the way.
Cruise Details
0
Explore the ancient Acropolis
from $2,290
SS 25%
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Sicily & Greece

Piraeus - Valletta - 7 Day Itinerary aboard Royal Clipper
  • Wander Athens Ancient Agora
  • Explore Pylos Navarino Bay
  • Explore Syracuse’s historical ruins
  • Visit Valletta’s museums palaces
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Set sail on a 7-day Mediterranean cruise from Piraeus to Valletta aboard the Royal Clipper, exploring historic Athens, Monemvasia's Byzantine fortress, and Pylos, famous for King Nestor’s Palace. Discover Sicily's Syracuse and Malta's Gozo, known for diving and coastal caves, before concluding in the fortified capital of Valletta.
Cruise Details
0
Admire the ruins of a temple on Naxos
from $17,395
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Ancient Empires: Athens to Istanbul

Athens - Istanbul - 12 Day Itinerary aboard Scenic Ikon
  • Explore Athens ancient Parthenon
  • Wander Hydra whitewashed homes
  • Discover Milos rock formations
  • Visit Heraklion Palace of Knossos
Starts / Ends
Piraeus / Istanbul
Activity Level
Variable
Join a 12-day Eastern Mediterranean cruise from the Greek islands to Istanbul on the Scenic Ikon, exploring ancient sites like Ephesus and the charm of Santorini and Hydra. Enjoy guided excursions that highlight regional traditions, historical landmarks, and delicious Mediterranean cuisine.
Cruise Details
0
Explore the stunning island of Santorini
from $18,360
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Greek Isles, Turkey & The Pyramids

Piraeus - Valletta - 12 Day Itinerary aboard Scenic Eclipse II
  • Explore Athens Parthenon
  • Tour Kusadasi historic Ephesus
  • Wander Agios Nikolaos harbor
  • See Cairo majestic Sphinx
Starts / Ends
Piraeus / Valletta
Activities
Archaeological Site Visits, Urban Exploration, Village Visits, Local Market Visits
Activity Level
Variable
Join a 12-day cruise on the Scenic Eclipse II, exploring the beautiful Turkish coast, ancient Ephesus, and the stunning sunsets of Santorini. Then journey to Egypt's Pyramids, visit Crete's Agios Nikolaos, Sicily's Taormina, and wrap up in Valletta, Malta, experiencing rich history and diverse cultures.
Cruise Details
0
Explore Sibenik on the Dalmatian Coast
from $6,599
EXPLORE

Greece & Italy Reflections

Venice to Athens - 9 Day Itinerary aboard World Traveller
  • Cruise scenic Corinth Canal
  • Tour historic Sibenik fortress
  • Explore the Delphi ruins
  • Discover Parga’s Venetian castle
Starts / Ends
Venice / Piraeus
Activity Level
Variable
Embark on this 9-day cruise aboard the World Traveller from Venice to Athens, exploring the Adriatic and Aegean Seas. Highlights include Venice’s canals, Sibenik’s fortresses, Parga’s vibrant coastal setting, Delphi’s ancient ruins, sailing the Corinth Canal, Nafplion’s Venetian castles, and Athens’ iconic landmarks.
Cruise Details
0
Stroll the ancient walkways of Athens
from $6,590
EXPLORE

Ancient Cities of the Mediterranean

Athens - Valletta - 8 Day Itinerary aboard Le Dumont-d'Urville
  • Explore ancient Athens landmarks
  • Walk Nafplion’s fortress paths
  • Discover Corfu’s old town
  • Tour Valletta’s historic streets
Starts / Ends
Athens / Valletta
Activity Level
Variable
Sail from Athens to Valletta on an 8-day cruise aboard Le Dumont-d’Urville. Visit Nafplion, Monemvasia, Gythio, Corfu, Gallipoli, and Syracuse. From ancient fortresses and neoclassical towns to volcanic coasts and baroque streets, explore the deep cultural heritage of Greece, Italy, and Malta along the Ionian and Aegean seas.
Cruise Details
0
The pastel houses of Ponza Town
from $3,320
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Rome to Athens

Civitavecchia - Piraeus - 10 Day Itinerary aboard Royal Clipper
  • Watch Stromboli’s active volcano
  • Discover Crotone’s Greek heritage
  • Wander Parga’s cobbled lanes
  • Visit Katakolon
Starts / Ends
Civitavecchia / Piraeus
Activity Level
Variable
Set sail on a 10-day Mediterranean cruise from Civitavecchia to Piraeus aboard the Royal Clipper, visiting stunning locations like the Pontine Islands, Lipari, Taormina, and the historic sites of Ancient Olympia. The journey also includes Pargа, Monemvasia, and concludes in Piraeus, granting access to Athens.
Cruise Details
0
Explore the ancient ruins of Rome
from $3,740
SS 25%
EXPLORE

Rome to Athens

Civitavecchia - Piraeus - 12 Day Itinerary aboard Star Clipper
  • Explore Ponza pastel houses
  • Wander Amalfi grand Duomo
  • Discover Lipari Acropolis
  • Visit Syracuse Parco Archeologico
Starts / Ends
Civitavecchia / Piraeus
Activities
Small Ship Sailing
Activity Level
Variable
Set sail on a 12-day Mediterranean cruise from Civitavecchia aboard the Star Clipper, visiting highlights like Amalfi's grand Duomo, the ancient ruins of Olympia, and the charming island of Sifnos. Conclude your journey in Piraeus, Athens' main port, after exploring stunning cliffs and historical sites along the way.
Cruise Details
0
49-60 of 79 Results

Cruise Line Options for Small Ship Cruises in Greece

Adventure Life partners with carefully selected small ship Greek Island cruises that offer top-quality experiences:

  • Variety Cruises – Specializes in intimate yachts and small ship cruising Greek Islands, with itineraries that include hidden harbors, cultural stops, and island-hopping adventures.
     
  • SeaDream Yacht Club – Luxurious yachting experience with exceptional service, fine dining, and water sports right off the ship.
     
  • Celestyal Cruises – Blends Greek hospitality with immersive itineraries across the Aegean, including both iconic and lesser-known islands.
     
  • Other Boutique Vessels – Adventure Life also offers Greek Island cruises in small ships such as the Galileo, Harmony V, and Panorama, each offering unique sailing routes and boutique comforts.

Tips for Planning Small Ship Cruises in the Greek Islands

Itinerary Choices and Port Highlights
Consider whether you’d prefer a classic  small ship Greek Island cruise that includes Mykonos, Santorini, and Crete, or a more offbeat itinerary exploring Naxos, Hydra, or Patmos.

Ship Amenities and Facilities
Small ship cruises in Greece vary from simple yachts to boutique luxury vessels. Decide if you’d like casual comfort or premium amenities such as onboard spas, water sports platforms, or gourmet dining.

Timing and Weather Considerations
The best time to be on small ship cruises in Greece is between May and October. May–June and September–October offer warm weather, fewer crowds, and excellent sailing conditions. July and August are the busiest and hottest months.

Budget
Costs for small ship Greek Island cruises can vary depending on the level of luxury and itinerary length. Small ship cruises typically range from mid-tier to luxury pricing but deliver exceptional value with included meals, tours, and cultural activities.

Booking and Cancellation Policies
Since small ship Greek Island cruises have limited capacity, booking early (6–12 months in advance) ensures your preferred itinerary and cabin type. Always review cancellation policies, which vary by small ship Greek Island cruises, and consider travel insurance for added flexibility.

Real experience. Honest advice.

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FAQs About Greek Island Small Ship Cruises

What is the best way to cruise the Greek islands?

The best way is aboard  Greek Island cruises small ships, which offers flexibility, access to hidden ports, and a more intimate, personalized travel experience.

What is the best month to cruise the Greek islands?

May, June, September, and October are ideal months for small ship cruises in Greece, with pleasant weather, fewer crowds, and smooth sailing conditions.

Is a Greek Isle cruise worth it?

Yes, small ship Greek Island cruises allow you to see multiple islands in one trip, enjoy authentic experiences, and access charming harbors that larger ships can’t reach.

What is the most breathtaking island in Greece?

Santorini is famous for its caldera views and sunsets. Meanwhile, less-visited places like Naxos or Symi you can visit on Greek Island cruises small ships offer equally stunning scenery with fewer crowds.

How far in advance should I book a small ship Greek island cruise with Adventure Life?

We recommend booking at least 6–12 months in advance, as small ship cruises through Greece have limited cabins and fill quickly, especially during peak summer months.

Kassandra Magruder Adventure Life employee profile
Kassandra M.
Golden light reflecting off the whitewashed buildings of Santorini
Greece

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