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Adventures in Santorini!

Top Santorini Trips & Tours in September 2026

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Discover Santorini in September 2026 on one of these 9 tours hand-selected by the travel experts at Adventure Life. Explore the best of during September 2026 as you enjoy Archaeological Site Visits, Village Visits, Small Ship Sailing, Hiking, and Local Market Visits. Prices for trips in September 2026 range from $2,410 to $38,590 for a vacation of 8 to 9 days. Choose any of the below 9 itineraries in September 2026 and customize it when you contact one of Adventure Life's expert Santorini trip planners.
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Traditional architecture in Greece.
from $3,090
Up to 30%
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
Explore the beautiful walkways of Santorini
from $4,524
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Greece Island Hopping

9 Day Itinerary
  • Visit Athens, the capital of Greece
  • See iconic landmark in Athens
  • Visit the charming town of Naoussa
  • Relax in Paros' beautiful beaches
  • Capture the famous Santorini sunset
  • Sample local wines in Santorini
  • Enjoy the beauty of Santorini
Starts / Ends
Athens / Athens
Activities
Wine Tasting
Activity Level
Relaxed
Embark on an unforgettable 9-day Greece island-hopping adventure, exploring the stunning islands of Athens, Paros, and Santorini. This journey will take you through a perfect blend of ancient history and breathtaking landscapes. Be ready for a trip filled with azure waters, sun-drenched beaches, delicious cuisine, and picturesque villages.
Tour Details
0
Explore colorful villages on Rhodes
from $38,590
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Greek Islands & Turkish Coastline

Roundtrip Athens - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Athens' sophistication
  • Discover Delos' mythological past
  • Experience Mykonos' whitewashed
  • Visit Patmos’ sacred cave
Starts / Ends
Athens / Athens
Activities
Local Market Visits
Activity Level
Variable
Set sail on an 8-day cruise from Athens aboard the Emerald Azzurra, discovering Greece and Turkey's coastal gems. Experience ancient sites like Delos and Mykonos, enjoy leisure in Santorini, and explore local markets, all while relaxing on your luxurious yacht.
Cruise Details
0
See the ancient world come alive in Athens
from $3,350
Up to 30%
EXPLORE

Classical Greece

Roundtrip Athens - 8 Day Itinerary aboard Harmony G
  • Explore Kea’s charming port
  • Discover Delos archaeological site
  • Visit Monemvasia’s medieval streets
  • Stroll Nafplion’s old town
Starts / Ends
Athens / Athens
Activity Level
Variable
Set sail on an 8-day cruise from Athens aboard the Harmony G, exploring the Cyclades, Crete, and the hidden gem of Kythira. Discover historic charm in Monemvasia and Nafplion while enjoying a unique blend of cruising and yachting.
Cruise Details
0
Visit charming Naxos
from $3,385
EXPLORE

Divine Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
  • Discover Ios golden beach
  • Swim Naxos crystal waters
  • Wander Mykonos vibrant alleys
  • Explore Delos sacred ruins
Starts / Ends
Lavrion / Lavrion
Activities
Hiking
Activity Level
Variable
Embark on an 8-day cruise aboard the Elysium through the enchanting Cyclades. Discover this enchanting paradise, holding ancient secrets, and embark on a journey to explore its beauty.
Cruise Details
0
Walking in Santorini
from $2,410
SS 25%
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
Activities
Small Ship Sailing
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
Wander through the maze of colorful buildings on Santorini
from $5,455
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Aegean Escape

Roundtrip Lavrion - 8 Day Itinerary aboard Gemaya
  • Explore Sifnos scenic trails
  • Discover Sikinos landscapes
  • Relax on Ios with pristine beaches
  • Visit Serifos with rugged landscape
Starts / Ends
Lavrion / Lavrion
Activities
Scuba Diving
Activity Level
Variable
Set sail on an 8-day cruise to the Aegean aboard the Gemaya, exploring stunning islands like Santorini and Milos. Discover whitewashed villages, hidden coves, and the rich traditions of Greece amidst a backdrop of beauty and myth.
Cruise Details
0
from $3,090
Up to 30%
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
Activities
Village Visits, Archaeological Site Visits
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
Explore colorful villages on Rhodes
from $16,290
EXPLORE

Classical Greece

Roundtrip Athens - 8 Day Itinerary aboard Emerald Azzurra
  • Explore Delos archaeological island
  • Wander Mykonos whitewashed island
  • Visit Bodrum seaport
  • Discover Rhodes old town
Starts / Ends
Athens / Athens
Activity Level
Variable
Embark on an 8-day cruise aboard the Emerald Azzurra from Athens, exploring Delos, Bodrum, Rhodes, Santorini, Chania, and Hydra. Discover ancient ruins, stunning landscapes, and charming harbors before returning to the historic Greek capital.
Cruise Details
0
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