10 Best Santorini Multiday Tours in May 2026

Get a customized trip to Santorini in May 2026

Plan a multi-country or regional adventure across Santorini in May 2026, 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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Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

40% OFF TODAY

Amazing Greece - May 2026

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

40% OFF TODAY

Duration12 days

From

USD 4,126

USD 2,476

Saving

USD 1,650

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The Great Odyssey - May 2026

4.8

(17 reviews )

No booking fees

Best price guaranteed

My spouse and I wanted to go on a second honeymoon, which we humorously called our "honeymoon in old age." Along the way, we met wonderful, kind-hearted people, saw beautiful places, and enjoyed delicious meals. The hotels were always comfortable and cozy. We were just as happy and excited on the last day of the tour as we were on the first. Thank you so much for everything!

Sightseeing ToursCruise

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english

Destinations

Istanbul, Athens, Mykonos, Santo

Istanbul, Athens, Mykonos, Santorini, Crete, Heraklion, Ankara, Cappadocia, Pamukkale, Izmir, Canakkale

Duration18 days

From

USD 4,450

USD 4,317

Saving

USD 134

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40% OFF TODAY

Best of Central Europe and Greece - May 2026

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

40% OFF TODAY

Duration20 days

From

USD 6,696

USD 4,018

Saving

USD 2,678

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40% OFF TODAY

Splendours of Central Europe, Balkans and Greece - May 2026

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

40% OFF TODAY

Duration27 days

From

USD 8,177

USD 4,906

Saving

USD 3,271

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5% OFF TODAY

Highlights of Greece - May 2026

(1 review )

No booking fees

Best price guaranteed

Had an amazing trip manager and great group of people to travel with

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Santorini, Meteora, Delp

Athens, Santorini, Meteora, Delphi, Mykonos, Paros

5% OFF TODAY

Duration11 days

From

USD 2,295

USD 2,180

Saving

USD 115

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5% OFF TODAY

Highlights of Greece with Island Hopping - May 2026

4.8

(5 reviews )

No booking fees

Best price guaranteed

I had an amazing time. Both trip managers were wonderful, super helpful and lots of fun. I really enjoyed all the places we went and the activities. Going in May was definitely a good idea, the weather was warm but not too hot and the crowds were an okay size.

City sightseeingBeach

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Santorini, Ios, Meteora

Athens, Santorini, Ios, Meteora, Delphi, Mykonos, Paros

5% OFF TODAY

Duration14 days

From

USD 2,715

USD 2,579

Saving

USD 136

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Highlights of Greece with Island Explorer - May 2026

(3 reviews )

No booking fees

Best price guaranteed

The island tours and optional experiences provided were so worthwhile! These experience allowed us the opportunity to truly experience the places we visited and learn fascinating and phenomenal pieces of information. The costsaver and local guides truly made the optional experiences a part of the trip we HAD to experience for every place we visited.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Delphi, Kalamba

Athens, Mykonos, Delphi, Kalambaka, Santorini

Duration12 days

From

USD 4,165

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Super Sales

Tirana to Santorini: The Albanian Riviera & Iconic Greek Islands - May 2026

(3 reviews )

No booking fees

Best price guaranteed

I loved my personal experience because of the friends I made and memories

Explorer

Tour Type

Small Group Tour

Accommodation

Hostel, Hotel, Resort

Age Range

18-39 yrs

Operated in

english

Destinations

Tirana, Santorini, Meteora, Athe

Tirana, Santorini, Meteora, Athens, Paros, Ios, Berat, Himare, Corfu

Duration18 days

From

USD 3,549

USD 3,443

Saving

USD 106

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Super Sales

Corfu to Santorini: Beach Days & Jaw-Dropping Views - May 2026

(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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Super Sales

One Week in the Greek Islands - May 2026

No booking fees

Best price guaranteed

Calling all nature lovers, beachside loungers and avid explorers – this eight-day adventure will take you to all the hotspots throughout the famous Greek Islands. Explore an ancient citadel in Athens, then take a ferry to Paros in the Aegean Sea. See traditional villages, natural swimming coves and maybe even take a ride to the sister island Antiparos for a local bite. Head to the village of Lefkes and explore the scenic olive-grove locale before a lunch of moussaka, dolmas and Greek salad. Head to Ios – a hub of vibrant nightlife and countless beaches to kick back on – and watch the sunset over an iconic city with some new mates. End it all in Santorini, where you can hike off the refreshing glass (or glasses) of the country’s most popular wine and sit down for another epic sunset. This is the perfect way to forge new friendships!

Adventure

Tour Type

Small Group Tour

Accommodation

Hotel, Hostel

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Santorini, Paros, Ios

Duration8 days

From

USD 1,505

USD 1,460

Saving

USD 45

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London to Santorini - May 2026

(2 reviews )

No booking fees

Best price guaranteed

Loved the fast paced trip and now many nights we were able to go out. the trip managers were also incredible and very knowledgeable

City sightseeing

Tour Type

Group Tour

Accommodation

Hostel, Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Paris, London, Santorini, Venice

Paris, London, Santorini, Venice, Florence, Rome, Athens, Mykonos, Paros, Beaujolais, Barcelona, French Riviera

Duration24 days

From

USD 4,295

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Athens to Santorini Island Hopping - May 2026

4.9

(19 reviews )

No booking fees

Best price guaranteed

Fantastic way to see some of the main islands in Greece

Sightseeing ToursBeach

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos, Paros

Duration8 days

From

USD 1,315

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London to Athens with Greek Island Hopping - May 2026

(3 reviews )

No booking fees

Best price guaranteed

Amazing experience!! met the best people and had the best time! London to Athens was very jam packed and exciting, the greek island hopping was relaxing but also had lots of parties so it was a great way to end the trip!!

Sightseeing ToursBeach

Tour Type

Group Tour

Accommodation

Hostel, Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

London, Athens, Paris, Venice, F

London, Athens, Paris, Venice, Florence, Rome, Mykonos, Paros, Santorini, Ios, Beaujolais, Barcelona, French Riviera

Duration27 days

From

USD 4,675

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The Greek Gems: Athens, Delphi, Meteora And Santorini, Spanish-speaking Guide - May 2026

18% OFF TODAY

Super Sales

The Greek Gems: Athens, Delphi, Meteora And Santorini, Spanish-speaking Guide - May 2026

Trip customizable

Best price guaranteed

Athens is one of the most historic cities in the world, among the oldest cities in Europe with a history of 3000 years. A fascinating town full of highlights and surprises. Visit the Acropolis museum and site and learn about Greek civilization. But remember that Athens is not just about antiquity; Athens will offer you plenty of opportunities to savour the best of the traditional Greek cuisine. Kalambaka is a picturesque town with narrow cobble-stoned streets and traditional houses, some of them built right next to the rocks and have a long tradition in the production of hand-made, wood-carved objects, but also in the making of religious icons that are painted by domestic artists. Some of the workshops are located outside the town’s centre. Don’t miss the opportunity to visit some of them. Crescent-shaped Santorini Island is the most precious gem of Cyclades islands. The island itself though hides several gems where with this tour, you are given the chance to explore, see and admire.

Art and architectureBeach

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

spanish

Destinations

Athens, Santorini, Kalambaka

18% OFF TODAY

Duration8 days

From

USD 1,600

USD 1,319

Saving

USD 281

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All Santorini Tours in May 2026

Page 3 of 44 Trips in Santorini during May 2026 with 315 Reviews

Get a customized trip to Santorini in May 2026

Page 3 of 44 Trips in Santorini during May 2026 with 315 Reviews

Amazing Greece - May 2026

The Great Odyssey - May 2026

Best of Central Europe and Greece - May 2026

Splendours of Central Europe, Balkans and Greece - May 2026

Highlights of Greece - May 2026

Highlights of Greece with Island Hopping - May 2026

Highlights of Greece with Island Explorer - May 2026

Tirana to Santorini: The Albanian Riviera & Iconic Greek Islands - May 2026

Corfu to Santorini: Beach Days & Jaw-Dropping Views - May 2026

One Week in the Greek Islands - May 2026

London to Santorini - May 2026

Athens to Santorini Island Hopping - May 2026

London to Athens with Greek Island Hopping - May 2026

The Greek Gems: Athens, Delphi, Meteora And Santorini, Spanish-speaking Guide - May 2026

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 2026

Page 3 of 44 Trips in Santorini during May 2026 with 315 Reviews

Get a customized trip to Santorini in May 2026

Page 3 of 44 Trips in Santorini during May 2026 with 315 Reviews