Have questions? We're here.
Cruising couples in the Mediterranean.

Greek Island Small Ship Cruises

Travel made your way ™
Talk with an expert
Build your ideal Greece trip. Call 800.344.6118
Start Planning My Trip
Filter (62 Results)
  • Start Date
    Months
    Years
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Greece
Relax on the sunny beaches of Paros
from $7,680
EXPLORE

At the heart of the Greek Islands

Roundtrip Athens - 8 Day Itinerary aboard Le Dumont-d'Urville
  • Explore vibrant Athens
  • Discover historic Patmos
  • Admire ancient Delos
  • Visit whitewashed houses in Amorgos
Starts / Ends
Athens / Athens
Activities
Archaeological Site Visits, Village Visits
Activity Level
Variable
Embark on an 8-day cruise aboard Le Dumont-d'Urville and explore Athens, Patmos, Amorgos, Milos, Delos, Paros, and Hydra. Visit historic sites, archaeological ruins, monasteries, villages, museums, and beaches, with a stop in Çeşme and sailing through the Santorini Caldera.
Cruise Details
0
The famous windmills of Mykonos
from $5,230
EBD 10%
EXPLORE

Sparkling Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya
  • See pristine waters of Milos
  • Explore Sifnos' vibrant culture
  • Enjoy swimming in Despotiko
  • Visit ancient ruins in Delos
Starts / Ends
Lavrion / Lavrion
Activities
Hiking
Activity Level
Variable
Embark on an 8-day cruise through the stunning Cyclades on the Gemaya, exploring charming islands like Milos, Sifnos, and Delos, rich in culture and natural beauty. Experience pristine beaches, delightful hiking, and vibrant local cuisine before concluding your adventure in Lavrion.
Cruise Details
0
Wander through the maze of colorful buildings on Santorini
from $6,870
EXPLORE

Cruising the Greek Islands of the Southern Aegean

Athens Roundtrip - 8 Day Itinerary aboard Le Laperouse
  • Explore Athens’ ancient monuments
  • Visit Patmos’ sacred sites
  • Discover Rhodes’ medieval streets
  • Marvel at Santorini cliffs
Starts / Ends
Athens / Athens
Activity Level
Variable
Embark on an 8-day journey aboard Le Laperouse from Athens, exploring Greece’s iconic islands and cultural landmarks. Visit Saint John sites in Patmos, explore Rhodes’ medieval streets, marvel at Santorini’s cliffs, discover Amorgos’ villages, delve into Delos’ ruins, enjoy Mykonos’ vibrant streets, and admire Nafplion’s fortress views.
Cruise Details
0
Sail the Mediterranean
from $2,500
SS 25%
EXPLORE

Greek Island Odyssey

Piraeus Roundtrip - 8 Day Itinerary aboard Star Flyer
  • Walk Ancient Athens landmarks
  • Explore Karpathos Harbor
  • Visit Ephesus Ruins
  • Explore Patmos Heritage
Starts / Ends
Athens / Piraeus
Activity Level
Variable
Sail for 8 days aboard Star Flyer on the Greek Island Odyssey through the Aegean Sea. Travel from Athens to Karpathos, Rhodes, Kusadasi, Patmos, and Andros, balancing iconic ports, historic sites, and relaxed sailing days before returning to Piraeus.
Cruise Details
0
Explore the ancient Acropolis
from $2,500
SS 25%
EXPLORE

Aegean Gems

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer
  • Walk Athens historic Agora
  • Explore Samos harbor ruins
  • Stroll Çeşme white streets
  • Discover Skyros village life
Starts / Ends
Piraeus / Piraeus
Activity Level
Variable
Discover Greece and Türkiye aboard Star Flyer on an 8-day sailing from Piraeus to Piraeus. Visit Athens’ historic Agora, stroll Samos’ harbor, explore Cesme’s streets, wander Skyros’ villages, relax on Skopelos beaches, and experience Poros’ cultural landmarks. Onboard, enjoy pools, lounges, a library, and a spa.
Cruise Details
0
Colorful local boats in Greece
from $15,995
EXPLORE

Wonders of the Greek Islands & Aegean Riviera

Roundtrip Athens - 11 Day Itinerary aboard Scenic Ikon
  • Wander Chania Venetian walls
  • Discover Paros whitewashed houses
  • Enjoy Marmaris colorful bazaars
  • Experience Kos Asklepion
Starts / Ends
Piraeus / Piraeus
Activities
Local Market Visits, Urban Exploration
Activity Level
Variable
Set sail on an 11-day Aegean Sea cruise aboard the Scenic Ikon, starting in Athens and visiting Rhodes, Kusadasi, and Mykonos. Experience vibrant markets, ancient sites, and stunning landscapes while enjoying guided excursions that reveal the region’s rich culture.
Cruise Details
0
The famous windmills of Mykonos
from $11,960
EXPLORE

The Cyclades, in the Wake of Le Ponant

Roundtrip Athens - 8 Day Itinerary aboard Le Ponant
  • Discover Kythnos
  • Visit Monemvasia
  • Experience Serifos
  • Discover the island of Polyaigos
Starts / Ends
Lavrion / Lavrion
Activities
Stand Up Paddle Boarding
Activity Level
Variable
Embark on an 8-day cruise aboard Le Ponant roundtrip from Athens. Sail from Lavrio port to the Cyclades, exploring Tinos and Polyaigos. Enjoy strolls on Serifos before heading southeast to discover Monemvasia's peninsula. Sail towards Kythnos, a rugged terrain. Spetses, "the island of Jasmine," offers tailored activities.
Cruise Details
0
Discover beautiful Symi island
from $6,870
EXPLORE

Greek Islands of the Southern Aegean – with Smithsonian Journeys

Athens Roundtrip - 8 Day Itinerary aboard Le Dumont-d'Urville
  • Explore Athens Acropolis landmarks
  • Visit Patmos monastery heritage
  • Discover colorful Symi harbor
  • Discover lively Mykonos streets
Starts / Ends
Athens / Hermes Hotel - Athens
Activity Level
Variable
Discover Greece on an 8-day voyage aboard Le Dumont-d'Urville, visiting Athens, Patmos, Symi, Amorgos, Milos, Delos, Mykonos, and Nafplion. Explore UNESCO World Heritage sites, charming villages, volcanic coastlines, and crystal-clear coves. Sail through the Santorini Caldera, walk historic streets, and experience authentic Greek island culture.
Cruise Details
0
Alone in Athens
from $6,630
EXPLORE

Landscapes and historic sites of the Peloponnese

Athens Roundtrip - 8 Day Itinerary aboard Le Dumont-d'Urville
  • Cross the iconic Corinth Canal
  • Visit Itea and ancient Delphi
  • Experience scenic Katakolon coastli
  • Wander historic Gythio streets
Starts / Ends
Athens / Athens
Activities
Wine Tasting
Activity Level
Variable
Embark on an unforgettable 8-day cruise aboard Le Dumont d'Urville from Athens through the stunning Peloponnese and the Corinth Canal. Explore Itea, Katakolon, Gythio, Monemvasia, Nafplion, and Hydra while discovering ancient landmarks, medieval towns, and spectacular coastal scenery.
Cruise Details
0
Sunset over Athens' port
from $7,270
EXPLORE

European Autumn in the Aegean Sea

Athens Roundtrip - 8 Day Itinerary aboard Le Champlain
  • See Athens Acropolis monuments
  • Explore Skiathos town
  • Explore Kavala old town
  • Discover Skiathos' white houses
Starts / Ends
Athens / Athens
Activity Level
Variable
Sail an 8-day cruise through Greece aboard Le Champlain, roundtrip from Athens. Visit Skiathos, Volos, Thessaloniki, Kavala, Limnos, and Hydra, combining UNESCO landmarks, ancient ruins, island towns, cultural walking tours, and scenic sailing along Mount Athos.
Cruise Details
0
Enjoy stunning views from the island of Santorini
from $2,500
EXPLORE

Eternal Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer
  • Explore Athens ancient Agora
  • Discover Milos volcanic landscapes
  • Visit Adamas Sarakiniko Bay
  • Enjoy Santorini black sand beaches
Starts / Ends
Piraeus / Piraeus
Activities
Small Ship Sailing
Activity Level
Variable
Embark on an 8-day cruise aboard the Star Flyer, exploring ancient sites in Greece and Turkey, including the Acropolis and the ruins of Halicarnassus. Visit beautiful destinations like Milos, Crete, Santorini, and Hydra before concluding your journey in Piraeus.
Cruise Details
0
The Monastery of the Holy Trinity (Agia Triada), one of the six active monasteries of Meteora in Greece
from $3,325
EBD 10%
EXPLORE

Gems of the Sporades & Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
  • Enjoy Edipsos thermal spring waters
  • Explore Oreoi fishing village
  • Discover Volos Meteora monasteries
  • Swim golden beaches of Skiathos
Starts / Ends
Lavrion / Lavrion
Activities
Snorkeling, Kayaking, Wildlife Viewing
Activity Level
Variable
Embark on an 8-day cruise through the Sporades, Northern Evia, and Cyclades on the Elysium, exploring stunning beaches, historic sites, and charming villages. Enjoy swimming, scenic strolls, and delicious local cuisine across Greece's captivating islands.
Cruise Details
0
13-24 of 62 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.

Talk with an expert trip planner 800.344.6118

Plan My Trip

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.

Tilly Pearson employee headshot
Tilly P.
Golden light reflecting off the whitewashed buildings of Santorini
Greece

Chat Greece with a specialist

Our team is waiting and ready to talk with you about your next adventure. So go ahead and book an appointment with one of our specialized trip planners.

Let's Chat
800.344.6118

Where is your next adventure?

Contact Chat Call

Why Travel With Us?

Expert Guidance

With deep destination expertise in complex travel, we advise on how to maximize your time, avoid common pitfalls, and get the most out of every part of your trip.

Unbiased Cruise Expertise

We're not tied to any one cruise line, so you receive honest guidance on the best ship and itinerary for you—not a sales pitch.

Peace of Mind

You'll work with a team of humans who get to know you, answer every question, and support you until you return home—we're always just a call or text away.

As Featured In

How it Works

Connect

No cost, no commitment. Talk with our experts about your dream trip.

Plan

Share your travel style—we match you with the right itinerary or create one just for you.

Book

Lock in knowing every detail is handled and you’re fully supported.

Travel

Enjoy a seamless journey—and unlock 5% off your next adventure.