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Greek Island Small Ship Cruises

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Historical Shipyard in Turkey
from $4,140
EXPLORE

Grand Voyage: Athens to Athens

Roundtrip Piraeus - 15 Day Itinerary aboard Star Flyer
  • Discover Mykonos’ harbor
  • Wander Dikili’s streets
  • Marvel at Istanbul’s skyline
  • Unwind in Skopelos sandy coves
Starts / Ends
Piraeus / Piraeus
Activity Level
Variable
Set sail on a 15-day cruise aboard the Star Flyer, exploring Greece and Turkey’s historic ports. Experience Athens, Mykonos, Istanbul, and picturesque islands while enjoying hands-on sailing and breathtaking coastlines.
Cruise Details
0
Athens Acropolis
from $2,820
EXPLORE

Sicily & Greece

Piraeus - Valletta - 9 Day Itinerary aboard Star Flyer
  • Explore Milos Sarakiniko Bay
  • Visit Chania Venetian harbor
  • Walk Gythio streets
  • Explore Valletta the walled city
Starts / Ends
Piraeus / Valletta
Activity Level
Variable
Experience a 9-day Mediterranean sailing cruise on the Star Flyer, exploring ancient Athens, stunning Milos, and the charming alleys of Chania. Visit historic sites in Gythio, Pylos, Syracuse, Gozo, and end in Valletta, famous for its fortified city and gardens.
Cruise Details
0
The towering ruins of the Acropolis rise over Athens
from $2,000
EXPLORE

Antiquity to Byzantium

Roundtrip Athens - 8 Day Itinerary aboard Galileo
  • Explore Epidaurus grand theater
  • Visit Mycenae and its Lion’s Gate
  • Discover Nafplion’s old town
  • Tour Delphi’s ruins
Starts / Ends
Athens / Athens
Activity Level
Variable
Set sail on an 8-day cruise aboard the MS Galileo, exploring Greece's rich history from Nafplion's Ancient Epidaurus to the Oracle of Delphi at Itea. Experience highlights like Mycenae's ruins, the Dirou Caves, and the Palace of Nestor before returning through the Corinth Canal to Athens.
Cruise Details
0
A stunning view of Nafplion, Greece
from $2,150
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Sicily & Greece

Valletta to Athens - 7 Day Itinerary aboard Star Flyer
  • Explore Valletta the walled city
  • Explore Syracuse ruins
  • Visit Pilos Navarino Bay
  • Stroll Nafplio waterfront
Starts / Ends
Valletta / Piraeus
Activity Level
Variable
Join a 7-day cruise from Valletta to Piraeus on the Star Flyer, exploring historic sites like Syracuse's archaeological park and Monemvasia's Byzantine fortress. Visit Nafplio's Venetian architecture before concluding in Piraeus, where you can explore Athens' Acropolis and Agora.
Cruise Details
0
Athens Acropolis
from $1,740
EXPLORE

Sicily & Greece

Piraeus - Valletta - 6 Day Itinerary aboard Star Clipper
  • Explore Athens ancient Agora
  • Walk Monemvasia twisting alleys
  • Wander Syracuse baroque piazzas
  • Discover Valletta capital
Starts / Ends
Piraeus / Valletta
Activities
Archaeological Site Visits, Small Ship Sailing
Activity Level
Variable
Embark on a 6-day Mediterranean cruise from Piraeus to Valletta aboard the Star Clipper, visiting historic sites in Greece, Italy, and Malta. Highlights include Monemvasia, Pilos, and Syracuse, concluding in Valletta, a UNESCO World Heritage site.
Cruise Details
0
Relax on the beaches of the Greek Mediterranean
from $24,580
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The Greek Islands, the Corinth Canal and Adriatic

Athens - Dubrovnik - 11 Day Itinerary aboard Emerald Kaia
  • Explore Delos archaeological site
  • Wander Mykonos town
  • Transit narrow Corinth Canal
  • Discover Lefkada castle ruins
Starts / Ends
Piraeus / Dubrovnik
Activities
Village Visits
Activity Level
Variable
Embark on an 11-day cruise from Athens to Dubrovnik aboard the Emerald Kaia, exploring the Ionian and Adriatic Seas. Visit historic sites, enjoy local culture, and relax in stunning coastal towns before concluding your journey in Dubrovnik.
Cruise Details
0
Explore beautiful Paros
from $11,006
No SS
EXPLORE

Crossroads of the Ancient World: Exploring Greece and Turkey

Roundtrip Athens - 11 Day Itinerary aboard National Geographic Orion
  • Explore Delos ancient ruins
  • Walk Ephesus ancient city
  • Explore Paros harbor towns
  • Visit Didim Apollo sanctuary
  • Visit Patmos monastery site
Starts / Ends
Athens / Athens
Activity Level
Variable
Explore the Greek Islands and Turkey on an 11-day cruise aboard National Geographic Orion. Travel from Athens and Lavrio to Delos, Patmos, Samos, Ephesus, Bodrum, Leros, Naxos, and Paros. Walk ancient ruins, visit monasteries, explore island villages, sail the Aegean Sea, and experience local culture and history.
Cruise Details
0
Ruins Athina Pronaia temple in Ancient Delphi
from $7,720
No SS
EXPLORE

Ancient Mediterranean: Exploring Greece, Croatia and Albania

Greece to Croatia - 8 Day Itinerary aboard National Geographic Orion
  • Navigate scenic Corinth Canal
  • Explore Delphi Ruins
  • Stroll Dubrovnik Walls
  • Taste Local Wines
Starts / Ends
Athens / Zadar
Activities
Hiking, Cooking Classes, Kayaking, Festival Visits, Urban Exploration, Wildlife Viewing, Stand Up Paddle Boarding
Activity Level
Variable
Embark on an 8-day Mediterranean cruise aboard the National Geographic Orion, sailing from Greece to Croatia with stops in Albania, Corfu, and Dubrovnik. Explore ancient ruins, UNESCO World Heritage sites, and coastal cultures on this expertly guided expedition.
Cruise Details
0
Sunset over Athens' port
from $2,410
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
Poros, Greece
from $2,410
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, Local Market Visits
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
Stone streets of Stari Grad on Hvar island
from $3,610
SS 25%
EXPLORE

Greece, Montenegro & Croatia

Athens - Venice - 12 Day Itinerary aboard Star Clipper
  • View beautiful Mykonos
  • Walk through sacred temples
  • Discover historic Dubrovnik
  • Explore the lovely Cres Town
  • Visit inviting Korcula
Starts / Ends
Piraeus / Venice
Activity Level
Variable
Join Star Clipper on this 12-day cruise from Athens to Venice. Relax on the teak decks of the majestic tall ship as it sails along the clear waters around Mykonos, Santorini, Katakolon, Corfu, Kotor, Dubrovnik, Korcula, Hvar, Cres, and Venice! Along the way, you can learn about the mythology born here and soak in the sun!
Cruise Details
0
Explore the ancient Acropolis
from $2,290
EXPLORE

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
The pastel houses of Ponza Town
from $3,320
EXPLORE

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
Cape Drastis at Corfu island in Greece
from $3,610
SS 25%
EXPLORE

Greece, Montenegro and Croatia

Venice - Piraeus - 12 Day Itinerary aboard Star Clipper
  • Explore Venice’s canals
  • Relax on Mali Losinj’s beaches
  • Stroll Gythio’s harbor
  • Admire Milos’ white cliffs
Starts / Ends
Venice / Piraeus
Activity Level
Variable
Set sail on a 12-day cruise from Venice to Piraeus on the Star Clipper, exploring Croatia, Montenegro, and Greece. Experience stunning destinations like Dubrovnik, Kotor, and Mykonos while enjoying leisure activities.
Cruise Details
0
View of Valletta
from $1,710
EXPLORE

Sicily & Greece

Valletta - Piraeus - 6 Day Itinerary aboard Star Flyer
  • Explore Valletta’s peninsula
  • Discover Syracuse’s vast ruins
  • Visit Pilos’ ancient palace
  • Enjoy cafes in Monemvasia
Starts / Ends
Valletta / Piraeus
Activity Level
Variable
Embark on a 6-day cruise from Valletta to Athens aboard the Star Flyer, exploring Sicily's archaeological wonders and Greece's historic sites. Experience relaxation at sea and visit ancient locales like Pilos and Monemvasia before concluding your journey in Piraeus.
Cruise Details
0
Explore Sibenik on the Dalmatian Coast
from $6,999
Save 30%
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
Suez Canal Bridge, Egypt
from $3,240
EXPLORE

Suez Canal Crossing

Piraeus - Safaga - 11 Day Itinerary aboard Star Flyer
  • Walk Athens Agora historic site
  • Ride Hydra hills scenic trail
  • Explore Monemvasia fortress
  • Sail through Suez Canal
  • Explore Bodrum’s ruins
Starts / Ends
Piraeus / Safaga
Activity Level
Variable
Embark on an 11-day cruise aboard Star Flyer, exploring Greece and Egypt. Begin in Athens, visit Hydra, Monemvasia, Santorini, and Bodrum, and then continue to Rhodos, Alexandria, and Port Said. Explore ancient ruins, stunning islands, and vibrant cultures, with highlights including the Suez Canal and the Red Sea's crystal-clear waters.
Cruise Details
0
37-54 of 67 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.

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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.

Eric Niskanen Adventure Life employee profile
Eric N.
Golden light reflecting off the whitewashed buildings of Santorini
Greece

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