Top Santorini Trips & Tours in September 2025

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.

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.

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.

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.

Explore the captivating beauty of the Cyclades on this 8-day cruise aboard the Elysium. Discover this enchanting paradise, holding ancient secrets, and embark on a journey to explore its beauty.

Join an 8-day cruise on the Variety Voyager, exploring Greece's beautiful islands like Mykonos and Santorini and historic sites like Delos and Knossos. Enjoy stunning landscapes, relax on Kythira, and experience the culture and cuisine of Greece.

Embark on an 11-day Mediterranean cruise aboard National Geographic Orion starting in Athens. Visit Delos, Patmos, and Chios’s medieval villages. Explore the ruins of Ephesus, and the Castle of St. Peter in Bodrum, and enjoy water activities on nearby islands. Capture Leros’s windmills, explore Santorini’s volcanic history, and discover Naxos’s culture.

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.

On this 8-day cruise through the Mediterranean on the Star Clipper, you can enjoy the traditional charm of the Southern Cyclades Islands. Discover the magic and mythology of the Greek Isles as you visit the small port towns of Rhodes and Hydra and the legendary island of Santorini. Visit sun-kissed beaches, ancient ruins, and modern cities along the way.