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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Recommended by

Greece Highlights: Athens, Mykonos & Santorini - May 2026

(2 reviews )

Trip customizable

Best price guaranteed

I referred to this tour company for a last minute service and Anthony was unbelievable helpful and informative. He attended to my needs in a very timely manner and was very professional the entire time. overall a 10/10 experience. Someone give Anthony a raise!

BeachChill out

Tour Type

Private Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini

Duration8 days

From

USD 2,044

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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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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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7% OFF TODAY

Treasures of Greece & The Islands - May 2026

4.8

(43 reviews )

No booking fees

Best price guaranteed

Wonderful trip with our guide Lisa. The itinerary was good, but many long bus rides-which is necessary to cover mainland Greece and get in as much as we did in 7 full days. Would have loved to have an overnight stay in Nafplio. Enjoyed staying in hotels within walking distance to the towns-made it really easy to just go during free times. The dinner buffets at the hotels were not my favorite but understand why since a couple nights we were getting into the hotels late due to traveling. Kalabaka and Meteora were a highlight for me. The Olive Farm and Cooking night were wonderful. Both the Santorini and Mykonos stays were wonderful. The optional catamaran excursion on Santorini was great.

Food toursLocal culture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Kalambaka, Olym

Athens, Mykonos, Kalambaka, Olympia, Nafplion, Santorini

7% OFF TODAY

Duration14 days

From

USD 7,295

USD 6,815

Saving

USD 480

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Super Sales

Greece: Walking in the Greek Islands - May 2026

(8 reviews )

No booking fees

Best price guaranteed

I highly recommend G Adventures for people traveling alone and want to step outside of the typical tourist locations and activities. The CEO was an absolute professional with great character and knowledge.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

18-100 yrs

Operated in

english

Destinations

Athens, Santorini, Tinos, Naxos

Duration8 days

From

USD 4,149

USD 4,025

Saving

USD 124

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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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Super Sales

Greece: Athens and Walking in the Greek Islands - May 2026

(8 reviews )

No booking fees

Best price guaranteed

Fantastic trip! Loved the food and the hikes. The local guides were fantastic.! They definitely added to the enjoyment of the trip. Beautiful scenery and included activities. Lovely, like- minded group of travellers and an awesome CEO!

Walking toursSightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

18-100 yrs

Operated in

english

Destinations

Athens, Santorini, Tinos, Naxos

Duration10 days

From

USD 4,999

USD 4,849

Saving

USD 150

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Super Sales

Premium Greece in Depth - May 2026

No booking fees

Best price guaranteed

Embark on a 16-day Premium journey exploring very the best of mainland Greece and the Cyclades. Whether it’s tracing a path through ancient ruins in Delphi, visiting secluded monasteries high in the Meteora Valley, or watching as the sun sets over the whitewashed buildings of Santorini, this is a country where the weight of history makes its presence felt. With plenty of opportunities to mingle with the locals, savour traditional Aegean cuisine and visit the acclaimed sites, this is a complete adventure into Greece’s sun-kissed heartland.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Guest House, Hotel, Resort, Luxury Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Athens, Santorini, Paros, Naxos

Athens, Santorini, Paros, Naxos, Kalambaka, Itea, Dimitsana

Duration16 days

From

USD 7,270

USD 7,052

Saving

USD 218

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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 4,030

USD 3,909

Saving

USD 121

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

4.8

(32 reviews )

No booking fees

Best price guaranteed

I found unique items in both countries and tried some unforgettable street food. The guide Ozgır was kind and knowledagble.

Cruise

Tour Type

Group Tour

Accommodation

Hotel, Ship Cabin

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Istanbul, Athens, Crete, Santori

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

Duration14 days

From

USD 3,950

USD 3,832

Saving

USD 119

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Best Of Turkey And Greece With Island Hopping - May 2026

4.8

(15 reviews )

No booking fees

Best price guaranteed

The tour pace was a bit intense, but with so many natural and historic sites to see, it felt worthwhile. I focused on gathering memories, taking tons of photos along the way. Our guides felt like travel companions, knowledgeable and warm.

Sightseeing ToursCruise

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Istanbul, Athens, Mykonos, Santo

Istanbul, Athens, Mykonos, Santorini, Ankara, Cappadocia, Pamukkale, Izmir, Samos

Duration15 days

From

USD 3,850

USD 3,735

Saving

USD 116

View Tour

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

View Tour

Super Sales

Journeys: Discover the Greek Islands - May 2026

No booking fees

Best price guaranteed

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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All Santorini Tours in May 2026

15 Trips in Santorini during May 2026 with 142 Reviews

Get a customized trip to Santorini in May 2026

15 Trips in Santorini during May 2026 with 142 Reviews

Greece Highlights: Athens, Mykonos & Santorini - May 2026

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

Best of Greece Luxury Tour - May 2026

Greek Island Hopper - May 2026

Treasures of Greece & The Islands - May 2026

Greece: Walking in the Greek Islands - May 2026

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

Greece: Athens and Walking in the Greek Islands - May 2026

Premium Greece in Depth - May 2026

Premium Greece Cyclades Islands - May 2026

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

Best Of Turkey And Greece With Island Hopping - May 2026

Premium Turkey & The Cyclades Islands in Depth - May 2026

Journeys: Discover the Greek 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

15 Trips in Santorini during May 2026 with 142 Reviews

Get a customized trip to Santorini in May 2026

15 Trips in Santorini during May 2026 with 142 Reviews