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Explore the stunning island of Santorini

Top Santorini Trips & Tours in October 2025

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Discover Santorini in October 2025 on one of these 8 tours hand-selected by the travel experts at Adventure Life. Explore the best of Santorini, Athens, Mykonos, Delos, and Paros during October 2025 as you enjoy cruises, archaeological site visits, small ship cruises, village visits, and beaches. Prices for trips in October 2025 range from $2,030 to $23,120 for a vacation of 8 to 9 days. Choose any of the below 8 itineraries in October 2025 and customize it when you contact one of Adventure Life's expert Santorini trip planners.
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Explore the beautiful walkways of Santorini
$3,989
EXPLORE

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:
Archaeological Site Visits, Village Visits, Wine Tasting
Activity Level:
Relaxed
Escape to Greece on this 9-day Island Hopping Adventure that will take you to Athens, Paros, and Santorini. Start your journey in Athens, where you'll explore the architectural wonders of the ancient world, including the Acropolis and the Parthenon. Taste some of the finest Greek cuisines at …
Tour Details
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Church in the center of Marpissa, Paros, Greece
$2,500
EBD
EXPLORE

Jewels of the Cyclades

8 Day Itinerary aboard Galileo
  • Dine at traditional Greek Tavernas
  • Enjoy a swim-stop at Poliegos
  • Explore Delos's archaeological site
  • Walk through Syros
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Variable
Take an 8-day cruise on the Galileo, which leaves and returns to Athens, to see the Aegean Islands, known for their white-washed villages and ports, bright skies, and crystal seas. During your trip, you can visit popular destinations like Santorini and Mykonos, as well as lesser-known islands such …
Cruise Details
0
The whitewashed cliffs of Santorini
$3,350
EBD
EXPLORE

Classical Greece

8 Day Itinerary aboard Harmony G
  • Explore the beautiful Cyclades
  • Visit the peaceful town of Chora
  • Tour the old quarter of Nafplion
  • Experience archaeological sites
Starts / Ends:
Athens / Athens
Activities:
Archaeological Site Visits, Snorkeling
Activity Level:
Variable
Board the Harmony G for a week-long round-trip cruise. On this 8-day cruise from and back to Athens, see Greece at its best: the beautiful white-washed Cycladic Islands of Santorini and Mykonos; Crete, the largest and southernmost Greek island; and the Peloponnese, with its historical treasures in …
Cruise Details
0
Wander through the maze of colorful buildings on Santorini
$4,915
EXPLORE

Aegean Escape

8 Day Itinerary aboard Gemaya
  • Visit Kythnos' famous baths
  • Explore the dreamy island of Sifnos
  • Explore Sarakiniko beach
  • Enjoy Santorini
  • See the sandy beaches of Magganari
Starts / Ends:
Lavrion / Lavrion
Activities:
Archaeological Site Visits, Kayaking, Local Market Visits, Small Ship Cruises, Snorkeling, Stand Up Paddle Boarding, Village Visits
Activity Level:
Variable
Explore the Aegean Sea's pristine Blue waters while cruising on the boutique yacht, Gemaya. This 8-day round-trip Greece cruise takes you around the Cyclades, to the famous Santorini and Milos islands, but most importantly, to lesser-known islands that are untouched, unspoiled, and …
Cruise Details
0
Milos
$2,850
EXPLORE

Divine Cyclades

Roundtrip Lavrion - 8 Day Itinerary aboard Elysium
  • Explore Cape Sounion
  • Discover the island of Delos
  • Experience Mykonos
  • Enjoy Santorini
Starts / Ends:
Delos / Sifnos
Activities:
Hiking, Small Ship Cruises
Activity Level:
Variable
Embark on an 8-day cruise aboard the Elysium and discover the stunning beauty of the Cyclades. The islands shine with beautiful light and vivid blue colors, surrounded by gorgeous beaches, clear waters, and white buildings. Each island has unique charm and beauty, offering a timeless and peaceful …
Cruise Details
0
Colorful local boats in Greece
$6,540
EXPLORE

Jewels of the Aegean Sea in Music

Athens - Antalya - 8 Day Itinerary aboard Le Laperouse
  • Visit islands of the Aegean Sea
  • Enjoy beautiful Rhodes and Nafplion
  • Visit colorful Kusadasi,Turkey
  • See ancient sacred sites on Delos
Starts / Ends:
Athens / Antalya
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Explore Jewels of the Aegean Sea in music on this 8-day cruise aboard Le Laperouse. Set sail from Athens to Antalya, and explore ports with access to the finest ancient sites of Greece. Explore the Cycladic gems of Delos and Mykonos, where you'll find UNESCO World Heritage-listed sites of …
Cruise Details
0
$2,500
EBD
EXPLORE

Jewels of the Cyclades

8 Day Itinerary aboard Panorama
  • Dine at traditional Greek Tavernas
  • Enjoy a swim-stop at Poliegos
  • Explore Delos's archaeological site
  • Walk through Syros
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing, Village Visits
Activity Level:
Variable
Take an 8-day cruise on the Panorama, which leaves and returns to Athens, to see the Aegean Islands, known for their white-washed villages and ports, bright skies, and crystal seas. During your trip, you can visit popular destinations like Santorini and Mykonos, as well as lesser-known islands such …
Cruise Details
0
Walking in Santorini
$2,030
EXPLORE

Southern Cyclades

8 Day Itinerary aboard Star Clipper
  • Explore beautiful Rhodes
  • Visit Halicarnassus
  • Discover breathtaking Santorini
  • Ride a donkey to a lookout point
Starts / Ends:
Piraeus / Piraeus
Activities:
Archaeological Site Visits, Small Ship Cruises, Small Ship Sailing
Activity Level:
Variable
The Star Clipper brings you closer to unique island cultures, ancient treasures, and the breathtaking beaches of Greece on a spectacular 8-day cruise. History lovers can seek out ruins, both ancient and from the Crusades of the Middle Ages. Shoppers can have a field day in the stores and galleries, …
Cruise Details
0
1-8 of 8 Results
TrustScore 4.8 | 387 reviews
TrustScore 4.8 of 5
total score
Based on 387 reviews on
review score
4 hours ago
We have used AL for decades now to plan trips. Kassandra has been with us from the start and has never disappointed. She knows our family and our quirks and is always willing to fit the trip to us. This time we made her work for the booking because of family member schedules. It has all come together for a great Christmas gift for many families.
Kris Rowe
review score
8 hours ago
Shannon could not have been more helpful in arranging our recent booking with Uncruise. Very knowledgeable, professional and pleasant to work with. I highly recommend Adventure Life.
Daniel
review score
19 hours ago
We keep coming back to Adventure-Life for custom tailored, out of the ordinary, non-touristy trips and they deliver the best every time. The trip planners know how to put together just what we are looking for.
Judith P. NYC
review score
1 day ago
Kassandra is knowledgeable, efficient and very pleasant to work with.
Fred Weeman
review score
3 days ago
The booking was processed efficiently and quickly. We got what we wanted.
Doug Laporte

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