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Explore the stunning island of Santorini

Santorini Sailing Cruises

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Experience the magic of Greece's Santorini with Adventure Life's selection of small ship sailing Cruises for 2026. Discover the stunning Southern Cyclades, from the historical gems of Rhodes to the breathtaking vistas of Santorini, where you can even ride a donkey to a lookout point. Join us on an 8-day adventure exploring unique island cultures, ancient treasures, and pristine beaches aboard the Star Flyer or Star Clipper. Whether you're into archaeological site visits, small ship cruising, or simply soaking in the relaxed pace of the journey, this trip offers something for everyone. Don't miss the chance to sail through this Mediterranean paradise and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Santorini
Traditional architecture in Greece.
from $2,871
EBD 10%
EXPLORE

Jewels of the Cyclades

Roundtrip Athens - 8 Day Itinerary aboard Galileo
  • Capture Santorini’s caldera views
  • Swim Poliegos turquoise waters
  • Stroll Folegandros cliffside views
  • Tour Delos sacred temples
Starts / Ends
Athens / Athens
Activity Level
Variable
Set sail on an 8-day cruise aboard the Galileo, exploring the beautiful Cyclades from Athens to islands like Santorini, Mykonos, and Folegandros. Enjoy swim stops, cultural experiences, and delightful Cycladic cuisine on this unforgettable journey.
Cruise Details
0
Walking in Santorini
from $2,410
Air Credit
EXPLORE

Southern Cyclades

Roundtrip Piraeus - 8 Day Itinerary aboard Star Flyer
  • Explore Piraeus vibrant port city
  • Wander Rhodes medieval streets
  • Discover Bodrum rich history
  • Admire Santorini whitewashed cliffs
Starts / Ends
Piraeus / Piraeus
Activity Level
Variable
Set sail for 8 days on the Star Flyer, exploring historic Aegean ports from Piraeus to Rhodes and Bodrum while enjoying stunning views in Santorini and Hydra. Experience local culture, cuisine, and relaxation, culminating in a memorable return to Piraeus.
Cruise Details
0
Vineyard in Greece
from $5,300
Up to 50%
EXPLORE

Wines of Greece

Roundtrip Athens - 8 Day Itinerary aboard Panorama
  • Visit Poros with fine Ionian wines
  • Wander Nafplio ruins of Mycenae
  • Walk Naxos charming villages
  • Admire Syros architecture
Starts / Ends
Athens / Athens
Activities
Wine Tasting
Activity Level
Variable
Join an 8-day Greek wine cruise aboard the Panorama, guided by expert Tim Clarke. Explore the evolution of Greek wine production through tastings, vineyard visits, and lectures, all while enjoying the rich agricultural culture of the region.
Cruise Details
0
A traditional Greek table setup known as a meze spread, specifically showcasing ouzo paired with various seafood appetizers
from $3,090
EXPLORE

Αegean Food & Culture Stories

Roundtrip Piraeus - 8 Day Itinerary aboard Galileo
  • Capture Santorini’s caldera views
  • Swim Poliegos turquoise waters
  • Stroll Folegandros cliffside views
  • Tour Delos sacred temples
Starts / Ends
Athens / Athens
Activity Level
Variable
Join an 8-day culinary cruise in the Cyclades on the Galileo, hosted by culinary expert Angelis Nannos. Experience daily tastings, learn about Aegean traditions, and explore beautiful islands while enjoying insights into the region's food and agriculture.
Cruise Details
0
Colorful local boats in Greece
from $8,280
EXPLORE

A Symphony at Sea: The Musical Traditions of Greece

Roundtrip Athens - 8 Day Itinerary aboard Le Champlain
  • Explore historic Athens landmarks
  • Marvel at Delos ruins
  • Enjoy Mykonos’ seaside charm
  • Relax in car-free Hydra
Starts / Ends
Athens / Athens
Activity Level
Variable
Set sail on Le Champlain for an 8-day round-trip Mediterranean Cruise from Athens through the Greek Islands. Explore Heraklion, Santorini, Rhodes, Amorgos, Delos, Mykonos, and Hydra. Discover ancient ruins, scenic landscapes, and charming whitewashed villages. Each destination reveals a unique part of Greece’s history, culture, and beauty.
Cruise Details
0
Enjoy stunning views from the island of Santorini
from $2,500
Air Credit
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
Village Visits, Archaeological Site Visits, Small Ship Sailing, Local Market Visits
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 famous windmills of Mykonos
from $13,995
EBD
EXPLORE

Sailing the Greek Islands

Roundtrip Athens - 12 Day Itinerary aboard MV Douglas Mawson
  • Wander Athens’ ancient sites
  • Explore Mykonos’ vibrant culture
  • Tour Ephesus’ ancient ruins
  • Relax on Patmos beaches
Starts / Ends
Athens / Piraeus
Activity Level
Variable
Set sail on a 12-day cruise aboard the Douglas Mawson through Greece's stunning islands, experiencing vibrant villages and rich Mediterranean culture. Discover historical gems like Rhodes, Santorini, and Ephesus while starting your adventure in Athens.
Cruise Details
0
Stone streets of Stari Grad on Hvar island
from $3,610
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
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
from $3,090
EXPLORE

Jewels of the Cyclades

Roundtrip Athens - 8 Day Itinerary aboard Panorama
  • Stroll Folegandros cliffside views
  • Tour Delos sacred temples
  • Swim Poliegos turquoise waters
  • Explore Poros neoclassical charm
Activity Level
Variable
Set sail on an 8-day cruise aboard the Panorama, exploring the beautiful Cyclades from Athens to islands like Santorini, Mykonos, and Folegandros. Enjoy swim stops, cultural experiences, and delightful Cycladic cuisine on this unforgettable journey.
Cruise Details
0
Ship passing through Suez Canal, in the background - the Suez Canal Bridge, also known as Al Salam Bridge
from $3,610
SS 25%
EXPLORE

Suez Canal Crossing

Safaga - Piraeus - 12 Day Itinerary aboard Star Flyer
  • Discover Safaga’s Red Sea coast
  • Transit the Suez Canal
  • Explore Cairo from Port Said
  • Walk Rhodes’ Old Town
Starts / Ends
Safaga / Piraeus
Activity Level
Variable
Embark on a 12-day cruise from Safaga to Athens aboard the Star Flyer, exploring Egypt's historic sites and Greece's stunning islands. Enjoy visits to the Suez Canal, Alexandria, Rhodes, Santorini, and more.
Cruise Details
0
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Eric Niskanen Adventure Life employee profile
Eric N.
Adventures in Santorini!
Greece

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