10 Best Santorini Multiday Tours in May 2026

Island Hopping: Athens, Mykonos, Santorini - May 2026

18% OFF TODAY

Halloween Super Sales

Island Hopping: Athens, Mykonos, Santorini - May 2026

Trip customizable

Best price guaranteed

Join our eight-day tour and indulge in the island beauty of Greece! Lay back and relax on the white sandy beaches in Mykonos and get a glimpse of its vivid nightlife while having a drink at one of its clubs. Indulge in the romantic essence of the island of Santorini, walk along its bright coastline, and enjoy an awe-inspiring sunset upon the white-washed houses and the endless Mediterranean Sea. Traditional local gastronomy and wine tasting will only enrich your Greek experience within the Cyclades islands.

Beach

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos

18% OFF TODAY

Duration8 days

From

USD 1,130

USD 932

Saving

USD 198

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Halloween Super Sales

Greek Highlights and Crete - May 2026

Trip customizable

Best price guaranteed

This tour of Greece will guide you through the famous hotspots of Athens, Santorini, and Crete. Begin your trip in Athens, discovering the fascinating mix of ancient history and contemporary attractions. You will uncover magnificent views of the Acropolis, which is visible from almost every part of the city. From here, you will catch a ferry to Santorini, known for its magnificent sunsets and beautiful beaches. It will be difficult not to fall in love with the sheer cliffs soaring above the turquoise waters! Discover the incredible restaurants and wineries before you catch a ferry to Crete, where you will visit Heraklion. Also known as Iraklio, this is a breathtaking port city and the capital of Crete. It is the most popular region on the island and the most beautiful! Discover the Venetian harbor, a fortress, several fountains, a busy shopping center, and many squares before you travel to Athens to end your tour of Greece!

Chill outBeach

Tour Type

Independent Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

English

Destinations

Athens, Santorini, Heraklion

Duration9 days

From

USD 2,152

USD 2,087

Saving

USD 65

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The Greek Gems: Athens, Delphi, Meteora And Santorini, Private Tour - May 2026

18% OFF TODAY

Halloween Super Sales

The Greek Gems: Athens, Delphi, Meteora And Santorini, Private Tour - May 2026

Trip customizable

Best price guaranteed

Enjoy this memorable 8-day private tour and get closer to Greece's beautiful history and mythology, while admiring stunning landscapes, and indulging in mouth-watering Greek food. See the best of Athens, the picturesque town of Kalambaka and the crescent-shaped Santorini Island, the most precious gem of Cyclades islands.

Art and architectureBeach

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, italian, french, german

Destinations

Athens, Santorini, Kalambaka

18% OFF TODAY

Duration8 days

From

USD 3,655

USD 3,014

Saving

USD 642

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Halloween Super Sales

Island Hopping in Greece - May 2026

(1 review )

Trip customizable

Best price guaranteed

We were looking for a customized, small group tour. We just returned from our trip and are more than highly pleased and satisfied of our experience. They planned an amazing itinerary, booked amazing hotels and transfers and tour guides went above and beyond to please us. We are already planning another trip next year and will be using these guys.

Sightseeing Tours

Tour Type

Independent Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

English

Destinations

Athens, Santorini, Mykonos

Duration8 days

From

USD 1,994

USD 1,934

Saving

USD 60

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Exploring Greece With Athens, Delphi, Meteora, Mykonos And Santorini, Private Tour - May 2026

18% OFF TODAY

Halloween Super Sales

Exploring Greece With Athens, Delphi, Meteora, Mykonos And Santorini, Private Tour - 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 has 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. Welcome to Mykonos, the world´s biggest party island. Mykonos is a place where nights roll effortlessly into daybreak and where meeting people is as easy as seeing them. Its nightlife is so active and the people so friendly that it is impossible not to become intoxicated from its lively atmosphere. 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

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, french, italian, german

Destinations

Athens, Kalambaka, Mykonos, Santorini

18% OFF TODAY

Duration9 days

From

USD 3,623

USD 2,987

Saving

USD 636

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Halloween Super Sales

Premium Greece Cyclades Islands - May 2026

No booking fees

Best price guaranteed

Let the charm of the Cyclades wash over you on this 9-day Premium island adventure in Greece. Start off in the storied city of Athens, explore the villages of Paros, uncover ancient riches in Naxos and soak up the views in Santorini. Hike a caldera, tour wineries, sample local kitron and take a cooking class with organic ingredients. Travel with a passionate local leader who’s eager to share the magic of their country as you discover fascinating histories, incredible food and welcoming locals.

BeachChill out

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Luxury Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Athens, Santorini, Paros, Naxos

Duration9 days

From

USD 4,475

USD 4,341

Saving

USD 134

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Halloween Super Sales

Athens and 04 Nights Greek Islands Cruise - May 2026

Trip customizable

Best price guaranteed

Begin with a night in Athens, once the heart of Ancient Greece, a powerful civilization and empire. You will quickly see that the city today is still dominated by 5th century BC landmarks such as the Acropolis. You will embark the cruise from here and sail towards Mykonos, and island with many beautiful beaches and world class entertainment. Sail to Türkiye and visit Kusadasi, a beach resort town on Türkiye’s western Aegean coast. The seafront promenade, marina and harbor are all lined with hotels and restaurants to greet visitors. Visit the significant Christian pilgrimage site of Patmos; its Cave of the Apocalypse is where John of Paramos is said to have written the Book of Revelations. In Rhodes and Heraklion, see ancient ruins and archaeological sites that date back to a time of medieval towns and fortresses. Your trip ends after a visit to Santorini, known for its whitewashed buildings, dazzling panoramas and romantic sunsets.

CruiseBeach

Tour Type

Cruise Tour

Accommodation

Hotel, Resort, Ship Cabin

Age Range

8-99 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos, Patm

Athens, Santorini, Mykonos, Patmos, Rhodes

Duration8 days

From

USD 1,574

USD 1,527

Saving

USD 47

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Halloween Super Sales

Exploring Greece and Its Islands featuring Classical Greece, Mykonos & Santorini - May 2026

4.8

(43 reviews )

No booking fees

Best price guaranteed

All great, except Collette was not great with the communication for the Istanbul extension. The Hagia Sofia visit was cancelled by Collette with no explanation. So our group booked it ourselves. But on arrival it was part of our Collette tour. Not sure what happened.

BeachChill out

Tour Type

Group Tour

Accommodation

Resort, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Athens, Chora, Mykonos, Oia, San

Athens, Chora, Mykonos, Oia, Santorini, Kalambaka, Arachova, Olympia, Tolo

Duration16 days

From

USD 5,199

USD 5,043

Saving

USD 156

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Halloween Super Sales

Premium Turkey & The Cyclades Islands in Depth - May 2026

No booking fees

Best price guaranteed

Dive into the magic of the Mediterranean on a 23-day Premium adventure through Turkey and Greece. Discover stunning islands and a sunken city, enjoy guided tours of Gallipoli, Troy, Ephesus, Antalya and more, and marvel at diverse landscapes, from the fairy chimneys of Cappadocia to the glittering Mediterranean Coast. Hop across to the storied city of Athens, explore the charming villages of Paros, uncover ancient riches in Naxos and soak up million-dollar views in Santorini. With knowledgeable local leaders and a group of keen travellers by your side, you’re never far away from an unforgettable moment.

BeachLocal culture

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Luxury Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Istanbul, Santorini, Konya, Capp

Istanbul, Santorini, Konya, Cappadocia, Athens, Paros, Naxos, Canakkale, Selçuk, Pamukkale, Kas, Antalya

Duration23 days

From

USD 11,130

USD 10,796

Saving

USD 334

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Halloween Super Sales

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

USD 4,535

Saving

USD 140

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Halloween Super Sales

Wonders of Athens Mykonos Santorini and Crete - 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 Heraklion on the island of Crete, boasting fascinating remnants from brilliant ancient civilizations. Explore the sandy beaches and traditional villages of these sun-drenched islands as you lose yourself in the vast and varied landscapes and ancient treasures. Catch a flight to Athens where you will end your tour of the Greek Islands!

Cultural, religious and historic sites

Tour Type

Independent Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

English

Destinations

Athens, Mykonos, Santorini, Heraklion

Duration10 days

From

USD 2,519

USD 2,443

Saving

USD 76

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Halloween Super Sales

Atlas & Atlantic Coast - 10 days - May 2026

No booking fees

Best price guaranteed

PRIVATE TOUR: Experience vibrant Marrakech, visit the beautiful Cascades D'Ouzoud waterfalls, see Lake Bin Ouidane, explore Sidi Moussa and Ait Bougamez and take the road less travelled up into the High Atlas Mountains for a taste of real Morocco. Top it all off with a relaxing break in coastal Essaouira.

CruiseSightseeing ToursBeach

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Marrakech, Athens, Santorini, Ai

Marrakech, Athens, Santorini, Ait Bougmez, High Atlas Mountains, Essaouira

Duration10 days

From

USD 2,095

USD 2,032

Saving

USD 63

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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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One Country - Numerous Cities And Islands - May 2026

18% OFF TODAY

Halloween Super Sales

One Country - Numerous Cities And Islands - May 2026

Trip customizable

Best price guaranteed

Experience the very best Greece has to offer on this 15-day tour that encompasses history, culture, gastronomy and lively nightlife. Start in Athens and dive into the history of one of Europe’s oldest cities in a country known as the cradle of western civilisation. Travel to the picturesque town of Kalambaka at the foot of the stunning Meteora rock formation. Then hit the town in Mykonos, the world’s greatest party island! It’s impossible not be intoxicated by the lively atmosphere, friendly people and the nights that roll into daybreak over the Aegean Sea. Round off the tour with a visit to some of the hidden gems of Santorini, the most iconic and beautiful of the Cyclades islands.

BeachArt and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Athens, Santorini, Aegina , Myko

Athens, Santorini, Aegina , Mykonos, Olympia, Delphi, Kalambaka, Thessaloniki

18% OFF TODAY

Duration15 days

From

USD 3,439

USD 2,836

Saving

USD 604

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All Santorini Tours in May 2026

Page 3 of 51 Trips in Santorini during May 2026 with 285 Reviews

Get a customized trip to Santorini in May 2026

Page 3 of 51 Trips in Santorini during May 2026 with 285 Reviews

Island Hopping: Athens, Mykonos, Santorini - May 2026

Greek Highlights and Crete - May 2026

The Greek Gems: Athens, Delphi, Meteora And Santorini, Private Tour - May 2026

Island Hopping in Greece - May 2026

Exploring Greece With Athens, Delphi, Meteora, Mykonos And Santorini, Private Tour - May 2026

Premium Greece Cyclades Islands - May 2026

Athens and 04 Nights Greek Islands Cruise - May 2026

Exploring Greece and Its Islands featuring Classical Greece, Mykonos & Santorini - May 2026

Premium Turkey & The Cyclades Islands in Depth - May 2026

London to Athens with Greek Island Hopping - May 2026

Wonders of Athens Mykonos Santorini and Crete - May 2026

Atlas & Atlantic Coast - 10 days - May 2026

London to Santorini - May 2026

One Country - Numerous Cities And Islands - 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 51 Trips in Santorini during May 2026 with 285 Reviews

Get a customized trip to Santorini in May 2026

Page 3 of 51 Trips in Santorini during May 2026 with 285 Reviews