10 Best Santorini Multiday Tours in May 2027

Get a customized trip to Santorini in May 2027

Plan a multi-country or regional adventure across Santorini in May 2027, with help from a local expert.

Canan KaraarslanTravel Expert in Egypt, Greece, Jordan, Morocco & Turkey
Julia KourafaTravel Expert in Greece
Angela GianniotiTravel Expert in Greece
Kate PolitiTravel Expert in England, France, Germany, Greece & Slovenia
Elena KyrimiTravel Expert in Greece & Italy

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Amazing Greece - May 2027

No booking fees

Best price guaranteed

Embark on an epic 12-day adventure through Greece, where ancient history meets vibrant island life and breathtaking landscapes. Begin your journey in Athens—the grandeur of the Acropolis and the bustling Plaka neighborhood awaits. Then, hop on a ferry to the glamorous island of Mykonos. Immerse yourself in the island paradise for four unforgettable days before setting sail to the idyllic Ios for a day and picturesque Santorini for 2 nights. The awe-inspiring sunsets, cliffside villages, and volcanic wonders of Santorini will captivate you. Next, venture into the ancient mainland of Greece beginning from Thessaloniki, a vibrant city boasting a rich cultural heritage. Continue your exploration in Kalambaka, where the magnificent monasteries of Meteora will leave you in awe. Get ready to say goodbye in Delphi, the ancient sanctuary of Apollo, before returning to Athens. Unleash the adventurer within and experience the best of Greece in 12 incredible days.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-75 yrs

Operated in

english

Destinations

Athens, Delphi, Mykonos, Santori

Athens, Delphi, Mykonos, Santorini, Ios, Thessaloniki

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Duration12 days

From

USD 4,126

USD 2,476

Saving

USD 1,650

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The Best of Greek Islands - May 2027

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Best price guaranteed

Did you know that Crete is home to Europe’s oldest city? On this 15-day trip, you’ll explore ancient ruins as well as the coastal villages off the Aegean Sea and beautiful Crete Islands. Take a ferry along the Cyclades Islands, sip wine in the vibrant port city of Chania and wander through the ruins at Knossos – the former capital of Minoan Crete. Hike the Caldera Rim to Oia in Santorini, unwind in the secluded seaside village of Sougia and learn about the ancient capital of Athens from your local leader.

Explorer

Tour Type

Small Group Tour

Accommodation

Guest House, Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Athens, Chania, Knossos, Sougia

Athens, Chania, Knossos, Sougia, Syros, Mykonos, Santorini, Heraklion

Duration15 days

From

USD 5,400

USD 5,238

Saving

USD 162

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Journeys: Discover the Greek Islands - May 2027

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Sail into a world of timeless charm and island magic on this 8-day journey through the Greek Islands. Wander the iconic windmills and seaside charm of Mykonos, explore the lush heart of Naxos with an expert guide, and take part in a meaningful wildlife conservation experience. Along the way, enjoy a farm-fresh lunch, dive into centuries of tradition, and end your adventure on the postcard-perfect cliffs of Santorini — where the sunsets are unforgettable and the history runs deep.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos, Naxos

Duration8 days

From

USD 3,399

USD 3,297

Saving

USD 102

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Journeys: Classical Greece and Her Island Jewels - May 2027

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Best price guaranteed

Step into the myth and magic of Greece on a journey where ancient history meets sun-drenched island life. Stand in awe before the ruins of Athens, wander through the cliff-top monasteries of Meteora, and sail across the Aegean to the legendary island of Delos with a local archaeologist as your guide. Along the way, explore timeless towns like Olympia and Nafplio, savour regional flavours, and soak up the beauty of a country where every stone tells a story.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos, Naxo

Athens, Santorini, Mykonos, Naxos, Kalambaka, Delphi, Olympia, Nafplion

Duration16 days

From

USD 5,999

USD 5,819

Saving

USD 180

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Best of Central Europe and Greece - May 2027

No booking fees

Best price guaranteed

Discover the perfect blend of culture, history, and island bliss on this 20-day Best of Central Europe and Greece Tour. Begin your journey in the heart of Europe, exploring iconic cities like Berlin, Prague, Munich, Vienna, Bratislava, and Budapest. Each destination offers a rich cultural tapestry, from fairy-tale architecture and imperial grandeur to dynamic city streets and fascinating local traditions. With guided tours, seamless travel, and time to soak in the atmosphere, you'll uncover the stories and soul of Central Europe. From there, head south to the ancient wonders and sun-soaked islands of Greece. Wander through the timeless ruins of Athens before island-hopping to Mykonos, Santorini, and Ios. Whether you're chasing the perfect sunset, indulging in delicious cuisine, or relaxing on a golden beach, the Greek leg of the journey offers the ultimate in leisure and beauty. With the perfect mix of exploration and relaxation, this tour promises an unforgettable adventure from Europe's cultural heart to its sparkling southern shores.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-75 yrs

Operated in

english

Destinations

Berlin, Athens, Budapest, Mykono

Berlin, Athens, Budapest, Mykonos, Santorini, Ios, Prague, Munich, Vienna

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Duration20 days

From

USD 6,696

USD 4,018

Saving

USD 2,678

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Splendours of Central Europe, Balkans and Greece - May 2027

No booking fees

Best price guaranteed

Embark on an unforgettable 27-day journey with our Best of Central Europe and Greece Tour, where history, culture, and breathtaking landscapes come together in perfect harmony. Explore a rich tapestry of iconic cities and vibrant islands, each brimming with its own unique character and stories. Wander through the imperial grandeur of Vienna, soak up the enchanting charm of medieval towns, and marvel at the stunning Adriatic coastline in Dubrovnik. Experience the timeless spirit of Athens, the cradle of ancient civilization, before diving into the lively, sun-soaked energy of Mykonos and other stunning Greek islands. This carefully crafted tour blends immersive cultural discoveries, architectural wonders, and moments of relaxation, ensuring you capture the true essence of every destination. Prepare to be captivated by history, beauty, and unforgettable experiences at every turn.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-75 yrs

Operated in

english

Destinations

Berlin, Athens, Budapest, Sofia

Berlin, Athens, Budapest, Sofia, Belgrade, Sarajevo, Trebinje, Shkoder, Ohrid, Skopje, Mykonos, Santorini, Ios, Prague, Munich, Vienna

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Duration27 days

From

USD 8,177

USD 4,906

Saving

USD 3,271

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Solo-ish Greece - May 2027

(4 reviews )

No booking fees

Best price guaranteed

It was wonderful to experience Greece with others without feeling like I should find a friend to travel with. Our CEO’s enthusiasm about the culture was contagious. Thanks for creating an active vacation experience!

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-100 yrs

Operated in

english

Destinations

Athens, Santorini, Tinos, Mykono

Athens, Santorini, Tinos, Mykonos, Naxos

Duration9 days

From

USD 2,699

USD 2,618

Saving

USD 81

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Corfu to Santorini: Beach Days & Jaw-Dropping Views - May 2027

(4 reviews )

No booking fees

Best price guaranteed

I summed it up in my comments about my two awesome CEOs, Oliver and Vas, but I would just like just like to add that this was my first trip with G Adventures, and (fingers crossed) definitely not my last! Greece is a beautiful, complex, and diverse country, and I'm so grateful to have experienced it through this tour. Exploring the lush forests of Corfu, seeing the ancient ruins in Athens, walking through a village in Naousa, Paros, visiting the beaches of Ios, and of course, the ending in the iconic town of Fira in Santorini, all of these incredible experiences and memories were only enhanced by my CEOs, and my travel groups. I honestly couldn't ask for more out of a trip. To this day, I'm still a little amazed that I got to experience it at all. What a gift!

Explorer

Tour Type

Small Group Tour

Accommodation

Hostel, Hotel, Resort

Age Range

18-39 yrs

Operated in

english

Destinations

Santorini, Corfu, Ios, Meteora

Santorini, Corfu, Ios, Meteora, Athens, Paros

Duration12 days

From

USD 2,499

USD 2,424

Saving

USD 75

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Zagreb to Santorini: 35 Unforgettable Days - May 2027

(1 review )

No booking fees

Best price guaranteed

Such an incredible experience. I appreciated the tour layout and destination planning. Felt that it all flowed very well together.

Explorer

Tour Type

Small Group Tour

Accommodation

Guest House, Hostel, Hotel, Resort, Villa

Age Range

18-39 yrs

Operated in

english

Destinations

Santorini, Zagreb, Konjic, Saraj

Santorini, Zagreb, Konjic, Sarajevo, Kotor, Zabljak, Budva, Tirana, Plitvice Lakes National Park, Berat, Himare, Corfu, Meteora, Athens, Split, Paros, Ios, Dubrovnik, Trebinje, Livno, Mostar

Duration35 days

From

USD 6,749

USD 6,547

Saving

USD 202

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Crete & Santorini Discovery - May 2027

(4 reviews )

No booking fees

Best price guaranteed

Lovely trip to Crete, showing the highlights of the island. It was nice to visit the smaller villages that I wouldn’t have known of. Beautiful scenery, clear blue water, and nice pebble beaches. The CEO Sakis was excellent and helped navigate us throughout the trip and recommended some really nice restaurants and bakeries. Ending in Santorini to see a different island with completely different vibe was a good way to end the trip.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Santorini, Chania, Agia Roumeli

Santorini, Chania, Agia Roumeli, Loutro, Irakleion

Duration8 days

From

USD 1,899

USD 1,842

Saving

USD 57

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All Santorini Tours in May 2027

10 Trips in Santorini during May 2027 with 13 Reviews

Get a customized trip to Santorini in May 2027

10 Trips in Santorini during May 2027 with 13 Reviews

Amazing Greece - May 2027

The Best of Greek Islands - May 2027

Journeys: Discover the Greek Islands - May 2027

Journeys: Classical Greece and Her Island Jewels - May 2027

Best of Central Europe and Greece - May 2027

Splendours of Central Europe, Balkans and Greece - May 2027

Solo-ish Greece - May 2027

Corfu to Santorini: Beach Days & Jaw-Dropping Views - May 2027

Zagreb to Santorini: 35 Unforgettable Days - May 2027

Crete & Santorini Discovery - May 2027

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Santorini Tours in May 2027

10 Trips in Santorini during May 2027 with 13 Reviews

Get a customized trip to Santorini in May 2027

10 Trips in Santorini during May 2027 with 13 Reviews