10 Best Santorini Multiday Tours in May 2026

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.

Halloween Super Sales

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

USD 4,166

Saving

USD 129

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Highlights Of Greece With Island Hopping - May 2026

8% OFF TODAY

Halloween Super Sales

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

8% OFF TODAY

Duration14 days

From

USD 2,715

USD 2,502

Saving

USD 213

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Halloween Super Sales

Gems and Islands of Greece - May 2026

Trip customizable

Best price guaranteed

Embark on an unforgettable journey through Greece, exploring ancient landmarks, captivating archaeological sites, and breathtaking islands. Start in Athens, the historic heart of Greece, where ancient wonders meet modern vibrancy. Venture to Delphi, the legendary city revered by ancient Greeks as the Center of the Earth. Continue with a scenic drive to Kalambaka, enjoying picturesque views of charming villages and towns. Arrive at Meteora, where dramatic rock formations host stunning monasteries. Delve into local culture and handicrafts before returning to Athens for an immersive city tour, visiting iconic sites like the Panathenaic Stadium and the Acropolis. Afterwards, sail to the cosmopolitan island of Mykonos, famous for its vibrant nightlife, exquisite cuisine, and beautiful beaches. Conclude your journey on the enchanting island of Santorini, with its turquoise waters and white-sand beaches. This comprehensive tour of Greece promises a blend of history, culture, and natural beauty, ensuring an experience you'll cherish forever.

Art and architectureBeach

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Athens, Santorini, Kalambaka, Mykonos

Duration9 days

From

USD 1,837

USD 1,782

Saving

USD 55

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Halloween Super Sales

Treasures of Athens and The Greek Islands - May 2026

Trip customizable

Best price guaranteed

Discover turquoise waters, white-sand beaches, ancient ruins, and fascinating archaeological sites with this tour of Athens and the Greek Islands! Begin your journey in Athens where you will visit the Temple of Olympian Zeus and see the world-famous Acropolis, two of the most iconic attractions in the Greek capital. Catch your ferry to Naxos and lose yourself in the beauty of the Greek Islands. This extraordinary island is home to some of the most beautiful beaches in Greece and is the perfect place to try windsurfing or kitesurfing. From there you will travel to Mykonos, home to the traditional village of Ano Mera and the glamorous street of Mayotanni. Experience the vibrant nightlife scene of this notorious party island before you set sail to Santorini to enjoy the breathtaking sunset views and see the dramatic rocky landscapes in this romantic destination. Make your way back to Athens where you will end your tour of Greece!

BeachArt and architecture

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Athens, Santorini, Naxos, Mykonos

Duration9 days

From

USD 1,732

USD 1,680

Saving

USD 52

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Halloween Super Sales

Athens with 07 Nights Greek Islands Cruise - May 2026

Trip customizable

Best price guaranteed

Discover the rich history, captivating culture, and delectable cuisine of the unforgettable Greek islands on this 7-night Cruise Journey. Begin your adventure in Athens, Greece’s historic capital, where you'll explore ancient ruins and iconic landmarks such as the Acropolis. Next, you'll sail to Kusadasi, Turkey, to marvel at the ancient city of Ephesus, one of the Seven Wonders of the Ancient World. Later, you'll arrive at Rhodes, where you can blend ancient and modern charm by visiting the medieval Acropolis at Lindos and wandering the Old Town. As you sail to Crete’s Agios Nikolaos, enjoy its beautiful Bay of Mirabello and legendary Lake Voulismeni. Next, you'll sail to Santorini, where you can relax amidst its stunning volcanic scenery and picturesque villages. Later, you'll arrive at Mykonos, soaking up the sun on its famous beaches, exploring the vibrant town, and perhaps taking a boat trip to Delos. As you sail to Milos, admire its unique volcanic landscapes and charming fishing villages before concluding your adventure back in Athens, reflecting on the rich history and cultural beauty of Greece.

CruiseSightseeing Tours

Tour Type

Independent Tour

Accommodation

Ship Cabin, Hotel, Resort

Age Range

8-99 yrs

Operated in

English

Destinations

Athens, Kusadasi, Rhodes, Crete

Athens, Kusadasi, Rhodes, Crete, Santorini, Mykonos, Milos

Duration9 days

From

USD 1,469

USD 1,425

Saving

USD 44

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Halloween Super Sales

Cycladic Gems - May 2026

Trip customizable

Best price guaranteed

Exerpience an extraordinary journey through the captivating Greek Islands of Mykonos, Santorini, Naxos, and Paros. Delight in the awe-inspiring splendor of the ancient Acropolis in Athens. Experience the vibrant nightlife of Mykonos and explore the renowned Santorini, famous for its breathtaking cliffside villages and invigorating hot springs. Revel in the hidden treasures of the Cycladic islands of Naxos and Paros, where you can unwind on pristine white beaches framed by charming whitewashed architecture

BeachCity sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Athens, Paros, Mykonos, Santorin

Athens, Paros, Mykonos, Santorini, Naxos

Duration12 days

From

USD 2,469

USD 2,395

Saving

USD 74

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Halloween Super Sales

Greek Isles Adventure with Crete - May 2026

Trip customizable

Best price guaranteed

Begin with a visit to Athens' ancient Acropolis, immersing yourself in its rich history. Next, set sail for Mykonos, renowned for its sandy beaches and vibrant nightlife. Wander through the narrow streets of Santorini, take in the volcanic landscapes, indulge in thermal spa relaxation, and witness the breathtaking sunset over the caldera. Lastly, explore Crete, the largest and most diverse of the Greek islands, where culture, history, and nature converge seamlessly

BeachChill outHoneymoon

Tour Type

Private Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Athens, Crete, Mykonos, Santorini

Duration13 days

From

USD 2,533

USD 2,457

Saving

USD 76

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Halloween Super Sales

Wonders of Athens Mykonos Santorini and Rhodes - May 2026

Trip customizable

Best price guaranteed

This trip will guide you through the most magnificent islands and cosmopolitan cities in Greece! Begin your journey in Athens, where you will see breathtaking views of the famous Acropolis in the heart of the city. Take a ferry to Mykonos, the bustling party island, famous for its delicious Mediterranean cuisine, exhilarating nightlife scene, and romantic resorts. Sail to Santorini for a stop on this magical island with beautiful beaches, world-class restaurants, and breathtaking views. Next, you will explore Rhodes, Greece’s largest Dodecanese Island, where you have the chance to hit the sandy beaches and explore the ancient ruins and remnants of the island. Catch a flight to Athens where you will end your tour of the Greek Islands!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini, Rhodes

Duration10 days

From

USD 2,624

USD 2,545

Saving

USD 79

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

18% OFF TODAY

Halloween 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 1,597

USD 1,317

Saving

USD 280

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All Santorini Tours in May 2026

Page 4 of 51 Trips in Santorini during May 2026 with 285 Reviews

Get a customized trip to Santorini in May 2026

Page 4 of 51 Trips in Santorini during May 2026 with 285 Reviews

London to Santorini - May 2026

Highlights of Greece with Island Hopping - May 2026

Gems and Islands of Greece - May 2026

Treasures of Athens and The Greek Islands - May 2026

Athens with 07 Nights Greek Islands Cruise - May 2026

Cycladic Gems - May 2026

Greek Isles Adventure with Crete - May 2026

Wonders of Athens Mykonos Santorini and Rhodes - 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 4 of 51 Trips in Santorini during May 2026 with 285 Reviews

Get a customized trip to Santorini in May 2026

Page 4 of 51 Trips in Santorini during May 2026 with 285 Reviews