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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7% OFF TODAY

Best Of Turkey And Greece With 3-night Cruise (small Group) - May 2026

4.9

(10 reviews )

No booking fees

Best price guaranteed

A tour of 8 people plus our guide and driver, a perfect number for our van. A most enjoyable 2 weeks seeing the highlights of Turkey with some fine company My expectations were pleasantly met as to the variety of our itinerary be it mosques, historical sites, Greek/Roman/Underground cities, temples, ruins, natural attractions. I felt at times we were rushed a little through some Greek/Roman cities however I understand we all move at a different pace to take in these wonders, mine perhaps being slower The hotels were a mix of mainly 3 star with the occasional 4 star and all were suitable for a quiet nights rest. The breakfasts and occasional dinner on offer did vary in quality but I personally found them to be fine. I opted for the single-supplement accommodation however it was random as to whether I was given a room with 2 single beds or 1 double bed (preferable), there was no option given at check-in so that was disappointing. I also chose the tour lunch pack but in hindsight there was no need as eating choices were abundant for our luncheons I was pleased I opted for the excursion to Troy and Gallipoli which included a visit to the ancient site of Pergamon en-route, and I considered the hotel in Canakkale the best hotel of the trip I would most certainly recommend Eskapas and this tour for some wonderful lifetime memories of Turkey

CruiseHoneymoon

Tour Type

Private Tour

Accommodation

Hotel, Ship Cabin

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Istanbul, Mykonos, Santorini, Rh

Istanbul, Mykonos, Santorini, Rhodes, Ankara, Cappadocia, Pamukkale, Izmir, Patmos

7% OFF TODAY

Duration12 days

From

USD 3,150

USD 2,926

Saving

USD 224

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7% OFF TODAY

Greek Island Explorer - May 2026

(2 reviews )

No booking fees

Best price guaranteed

All of our accommodations and transportation every place we visited in Greece on this trip were top notch. Comfortable and safe, and at each hotel location there was a lot to do within walking distance.

Natural landmarks sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos

7% OFF TODAY

Duration10 days

From

USD 3,225

USD 2,995

Saving

USD 230

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7% OFF TODAY

Mainland Greece And Islands - May 2026

4.8

(20 reviews )

No booking fees

Best price guaranteed

Taking this tour across Greece’s mainland and islands was such a rich and layered experience. Each day had its own flavor, blending history, culture, and just enough downtime to take it all in. Our guide, Stelio, was amazing at sharing stories that brought Greek mythology and history into each place we visited, and I felt genuinely connected to each site—Delphi and Meteora especially were something else. The hotels were comfortable and conveniently placed, which made it easy to enjoy some solo exploration. I have to give a nod to Alex from Eskapas for his seamless organization; everything felt thought-out from start to finish. Honestly, it’s rare to travel without a hitch, but this trip managed it, and I’m really glad I chose Eskapas.

AdventureSightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Athens, Mykonos, Delphi, Olympia

Athens, Mykonos, Delphi, Olympia, Kalambaka, Patmos, Santorini

7% OFF TODAY

Duration10 days

From

USD 3,300

USD 3,066

Saving

USD 234

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16% OFF TODAY

Athens, Mykonos & Santorini - May 2026

4.9

(7 reviews )

No booking fees

Best price guaranteed

Amazing sunset view and beautiful Santorini blue domes.The Acropolis tour is very informative and awesome tour guide.I love Mykonos too,it has its own magic.The town has its own character.Over all its a wonderful and must do tour experience.

Chill out

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini

16% OFF TODAY

Duration7 days

From

USD 2,580

USD 2,175

Saving

USD 405

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

18% OFF TODAY

Super Sales

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

(3 reviews )

Trip customizable

Best price guaranteed

I like Bookmundi because it lets me shop and scan all the tours available in the place i want to visit. It summarizes different tour companies and I choose which one I want. Besides that, their customer service is fast in responding if you have any questions. I will be using Bookmundi again. You can trust them 100%

Art and architectureBeach

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, french, italian

Destinations

Athens, Kalambaka, Santorini

18% OFF TODAY

Duration8 days

From

USD 1,528

USD 1,260

Saving

USD 268

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Island Hopping, The Cyclades Gems: Mykonos, Santorini - May 2026

18% OFF TODAY

Super Sales

Island Hopping, The Cyclades Gems: 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 into the romantic essence of the island of Santorini, walk along its bright coastline, and enjoy 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

Mykonos, Santorini

18% OFF TODAY

Duration8 days

From

USD 657

USD 542

Saving

USD 115

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18% OFF TODAY

Super Sales

Escape To Santorini, 3 Days - May 2026

(1 review )

Trip customizable

Best price guaranteed

All things went well. Thank you.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Santorini

18% OFF TODAY

Duration3 days

From

USD 176

USD 145

Saving

USD 31

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35% OFF TODAY

Best of Greece Luxury Tour - May 2026

No booking fees

Best price guaranteed

Discover the legendary beauty and fascinating mythology of Greece throughout the mainland and the precious islands of Mykonos and Santorini for 4 days each. Explore the 'cradle of Western civilization' on the 15-day Best of Greece to uncover all the incredible highlights on a comfortable and well-paced cultural adventure. Witness the changing landscapes and the seamless blend of ancient and cosmopolitan from Athens to Corinth, Meteora, and Olympia.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-95 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini, Nafp

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

35% OFF TODAY

Duration15 days

From

USD 9,225

USD 5,996

Saving

USD 3,229

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18% OFF TODAY

Greek Island Hopper - May 2026

(8 reviews )

No booking fees

Best price guaranteed

It is very relaxing and lots to do. The food is amazing.

Natural landmarks sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos

18% OFF TODAY

Duration10 days

From

USD 5,650

USD 4,644

Saving

USD 1,006

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50% OFF TODAY

Cycladic Explorer: Athens – Mykonos – Santorini | 10 Days - May 2026

4.7

(21 reviews )

No booking fees

Best price guaranteed

Excellent service while enjoying magnificent views. Overall, the tour was successful! Thank you!

Beach

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini

50% OFF TODAY

Duration10 days

From

USD 4,700

USD 2,350

Saving

USD 2,350

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Island Hopping: Athens, Mykonos, Santorini - May 2026

18% OFF TODAY

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 1,133

USD 934

Saving

USD 199

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7% OFF TODAY

Classical Greece And Turkey With 3-day Cruise (small Group) - May 2026

4.7

(16 reviews )

No booking fees

Best price guaranteed

My cousin Andy and I finally made our long-planned trip to Greece a reality, and finding a tour that also included a cruise and Turkey’s top sites was the icing on the cake. We’re so glad we booked this one!

Cruise

Tour Type

Group Tour

Accommodation

Hotel, Ship Cabin

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Istanbul, Athens, Mykonos, Patmo

Istanbul, Athens, Mykonos, Patmos, Santorini, Ankara, Cappadocia

7% OFF TODAY

Duration11 days

From

USD 3,800

USD 3,530

Saving

USD 270

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

18% OFF TODAY

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 3,664

USD 3,021

Saving

USD 643

View Tour

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

18% OFF TODAY

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 3,632

USD 2,994

Saving

USD 637

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All Santorini Tours in May 2026

Page 2 of 50 Trips in Santorini during May 2026 with 289 Reviews

Get a customized trip to Santorini in May 2026

Page 2 of 50 Trips in Santorini during May 2026 with 289 Reviews

Best Of Turkey And Greece With 3-night Cruise (small Group) - May 2026

Greek Island Explorer - May 2026

Mainland Greece And Islands - May 2026

Athens, Mykonos & Santorini - May 2026

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

Island Hopping, The Cyclades Gems: Mykonos, Santorini - May 2026

Escape To Santorini, 3 Days - May 2026

Best of Greece Luxury Tour - May 2026

Greek Island Hopper - May 2026

Cycladic Explorer: Athens – Mykonos – Santorini | 10 Days - May 2026

Island Hopping: Athens, Mykonos, Santorini - May 2026

Classical Greece And Turkey With 3-day Cruise (small Group) - May 2026

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

Exploring Greece With Athens, Delphi, Meteora, Mykonos And Santorini, Private Tour - 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 2 of 50 Trips in Santorini during May 2026 with 289 Reviews

Get a customized trip to Santorini in May 2026

Page 2 of 50 Trips in Santorini during May 2026 with 289 Reviews