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.

7% OFF TODAY

Amazing Greece : Athens, Mykonos, Paros And Santorini - May 2026

(5 reviews )

No booking fees

Best price guaranteed

I was impressed with pre booking process with Alex from Eskapas. He customized the trip and he was very patient with us. We modified our itinerary many times and he answeres all of our questions. I was very confident that we had chosen the right tour company. The promptness with which we were greeted at Athens airport, and the pick-up and drop-off to the hotels and airport were impressive. We really liked all the hotels that were chosen for us. Overall a great experience. Highly recommend.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Athens, Mykonos, Santorini, Paros

7% OFF TODAY

Duration12 days

From

USD 2,900

USD 2,697

Saving

USD 203

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

18% OFF TODAY

Super Sales

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

(2 reviews )

Trip customizable

Best price guaranteed

Overall our trip was awesome and I have pir most amazing guide to thank for that. With every question or concern I sent Katerina, her attention to detail eased my mind. My friends and I were very pleased and we will be booking with Tourradar again and again. Thank you Katerina for all did to make our trip a dream vacation.

Art and architectureBeach

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Athens, Kalambaka, Mykonos, Santorini

18% OFF TODAY

Duration9 days

From

USD 1,419

USD 1,170

Saving

USD 249

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7% OFF TODAY

Best Of Greece | 11 Days - May 2026

4.8

(21 reviews )

No booking fees

Best price guaranteed

Mykonos and Santorini were beyond beautiful! I was impressed by how smooth everything went from start to finish. The tour was well-paced, and we got to see so much without feeling rushed.

Sightseeing ToursBeach

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Athens, Santorini, Olympia, Delp

Athens, Santorini, Olympia, Delphi, Kalambaka, Mykonos

7% OFF TODAY

Duration11 days

From

USD 2,975

USD 2,767

Saving

USD 208

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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 2,930

Saving

USD 221

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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 3,069

Saving

USD 231

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Greek Island Hopping - May 2026

4.8

(40 reviews )

No booking fees

Best price guaranteed

I had the most fantastic time island hopping through Greece. The views were absolutely beautiful, but a lot of it was due to our fantastic trip manager, *Personal details removed by Feefo*, who made sure that we were having a fantastic time all the time no matter what we were doing no matter where we went. He went above and beyond and made sure that even during our free time when he didn’t need to that, we were having reservations at dinner or going out somewhere fun and having drinks and he just did a really absolutely fantastic job. And although my group was smaller than the average and made it so it was really intimate and that we were able to connect with the other travellers on the group, and I made some lifelong friends. And of course Greece is absolutely and incredible country and has some many amazing things to see.

BeachChill outAdventure

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Mykonos, Paros, Santorin

Athens, Mykonos, Paros, Santorini, Ios

Duration11 days

From

USD 1,735

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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 1,531

USD 1,262

Saving

USD 269

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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 659

USD 543

Saving

USD 116

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Greece Trip: 12 Days - FnEZ EVOLUTION 25+ - May 2026

No booking fees

Best price guaranteed

Dive headfirst into the sun-soaked islands of Greece with this 12-day trip, blending underwater exploration with classic island-hopping. Kicking off in Athens and winding down in the postcard-perfect Santorini, you’ll travel through Ios and Crete, sampling regional cuisine and lively nightlife along the way. The highlight of this tour package is its focus on scuba diving—ideal for those eager to discover vibrant marine life and hidden underwater treasures in the Aegean Sea. Group accommodation, daily meals, and all transportation are included, leaving you free to soak up the Mediterranean lifestyle. For travelers craving both adventure and relaxation, this journey offers the best of both worlds: thrilling dives by day, unforgettable sunsets by night. Unique selling point: curated diving experiences in some of Greece’s most iconic and beautiful locations.

Scuba diving

Tour Type

Group Tour

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Crete, Ios, Santorini

Duration12 days

From

USD 3,130

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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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Santorini and Crete Walk - May 2026

(2 reviews )

No booking fees

Best price guaranteed

Excellent itinerary, the best way to see Greece, on foot

Walking tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Santorini, Chania, Akrotiri, Pyr

Santorini, Chania, Akrotiri, Pyrgos, Heraklion, Loutro, Hora Sfakion

Duration8 days

From

USD 1,390

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50% 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

50% OFF TODAY

Duration15 days

From

USD 9,225

USD 4,612

Saving

USD 4,613

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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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All Santorini Tours in May 2026

Page 3 of 120 Trips in Santorini during May 2026 with 1,157 Reviews

Get a customized trip to Santorini in May 2026

Amazing Greece : Athens, Mykonos, Paros And Santorini - May 2026

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

Best Of Greece | 11 Days - May 2026

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

Greek Island Explorer - May 2026

Mainland Greece And Islands - May 2026

Greek Island Hopping - May 2026

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

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

Greece Trip: 12 Days - FnEZ EVOLUTION 25+ - May 2026

Escape To Santorini, 3 Days - May 2026

Page 3 of 120 Trips in Santorini during May 2026 with 1,157 Reviews

Santorini and Crete Walk - May 2026

Best of Greece Luxury Tour - May 2026

Athens, Mykonos & Santorini - 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 120 Trips in Santorini during May 2026 with 1,157 Reviews

Get a customized trip to Santorini in May 2026

Page 3 of 120 Trips in Santorini during May 2026 with 1,157 Reviews