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Explore the stunning island of Santorini

Top Santorini Trips & Tours in September 2025

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Discover Santorini in September 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 Hydra during September 2025 as you enjoy cruises, archaeological site visits, small ship cruises, beaches, and village visits. Prices for trips in September 2025 range from $2,030 to $6,900 for a vacation of 8 to 9 days. Choose any of the below 8 itineraries in September 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
0
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
$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
Colorful local boats in Greece
$3,490
EXPLORE

Classical Greece

Roundtrip Athens - 8 Day Itinerary aboard Variety Voyager
  • Explore the beautiful Cyclades
  • Discover the palace of King Minoas
  • Tour the old quarter of Nafplion
  • Experience archaeological sites
Activities:
Archaeological Site Visits, Small Ship Cruises, Snorkeling
Activity Level:
Variable
Classical Greece shows Greece at its best: the beautiful white-washed Cycladic Islands of Santorini and Mykonos, Crete - the largest and southern-most Greek Island, and the Peloponnese with Monemvassia and Nafplion and their historical treasures. Add to these destinations the less known and quaint …
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 | 415 reviews
TrustScore 4.8 of 5
total score
Based on 415 reviews on
review score
2 hours ago
Excellent service, great hotels and well organized excursions with expert guides! Highly recommended!
Shadi Dalili
review score
1 day ago
Clara Tort has been our Travel Advisor for Buenos Aires, then for Iguazu, then for Mendoza and Aconcagua Trekking, and then for Patagonia and Fitz Roy trekking. She has navigated with us through our travels, and now we are coming back for more- onto Machu Pichu and Peru.
Gus ORDONEZ
review score
1 day ago
Mary Curry made the experience wonderful for the second time. She is the reason we returned to Adventure Life to book our second cruise on WindStar. She is tireless, well informed, pleasant to work with and totally reliable. If you offer employees bonuses, give her one! there who answered to phone to help us book shore excursions were also very good and easy to work with - and we demand rather an lot of help.
Laura Flanagan
review score
1 day ago
The people assisting you have traveled with many of these companies or done the very same trip in the past. That kind of experience in invaluable when selecting a trip for yourself.
Sue Stephens
review score
1 day ago
Kaweskar tour Skorpios III Fantastic trip. Great food, wonderful scenery. Very fortunate the tour was under-subscribed (32 of 90 possible bookings) so it was really comfortable. Half this number was comprised of a tour from USA. We shared a table with an older couple - Ian and Helen, but everyone was friendly and excursions were efficiently run. We benefited from a requested cabin upgrade which saw us in the best suite.
John

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