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.

10% OFF TODAY

Halloween Super Sales

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

10% OFF TODAY

Duration10 days

From

USD 3,300

USD 2,977

Saving

USD 323

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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

USD 1,683

Saving

USD 52

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18% OFF TODAY

Halloween Super Sales

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

18% OFF TODAY

Duration7 days

From

USD 2,580

USD 2,110

Saving

USD 470

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Halloween Super Sales

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

USD 3,036

Saving

USD 94

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37% OFF TODAY

Halloween Super Sales

Best of Greece - 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

37% OFF TODAY

Duration15 days

From

USD 9,225

USD 5,816

Saving

USD 3,409

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20% OFF TODAY

Halloween Super Sales

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

20% OFF TODAY

Duration10 days

From

USD 5,650

USD 4,505

Saving

USD 1,145

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Treasures Of Greece & The Islands - May 2026

9% OFF TODAY

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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

9% OFF TODAY

Duration14 days

From

USD 7,295

USD 6,611

Saving

USD 684

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

52% OFF TODAY

Halloween Super Sales

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

52% OFF TODAY

Duration10 days

From

USD 4,700

USD 2,280

Saving

USD 2,421

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

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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

10% OFF TODAY

Duration11 days

From

USD 3,800

USD 3,428

Saving

USD 372

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Halloween Super Sales

Greek Island Hopping: Paros, Ios & Santorini Sunsets - May 2026

(6 reviews )

No booking fees

Best price guaranteed

It was a great trip. There was a lot of fun’s things to do both included and optional. Ten CEO was also really good.

Adventure

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Hostel

Age Range

18-39 yrs

Operated in

english

Destinations

Athens, Santorini, Paros, Ios

Duration7 days

From

USD 1,499

USD 1,454

Saving

USD 45

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Halloween 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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Halloween Super Sales

Dubrovnik to Santorini - May 2026

No booking fees

Best price guaranteed

Wind your way down through some of Mediterranean Europe’s most charming towns, beaches and islands on this journey from the Adriatic to the Aegean. Start off with a tour of Dubrovnik’s enchanting walled city before heading south along the spectacular Dalmatian coast to Montenegro. Venture off the tourist trail for a taste of old-time Balkans in Albania and Macedonia, take time out in provincial Syros, and then eat, drink and sunbathe your way through the good times on offer in Mykonos and Santorini. A region of breathtaking scenery, legendary history and ever-enticing cuisine, this journey through Eastern Europe serves up a slice of the Mediterranean with a Balkans backdrop.

Sightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House, Home-stay, Hostel

Age Range

15-99 yrs

Operated in

english

Destinations

Dubrovnik, Santorini, Pelister N

Dubrovnik, Santorini, Pelister National Park, Kastoria, Litochoro, Mount Olympus, Athens, Syros, Mykonos, Kotor, Tirana, Berat, Lake Ohrid, Skopje

Duration22 days

From

USD 6,800

USD 6,596

Saving

USD 204

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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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All Santorini Tours in May 2026

Page 3 of 89 Trips in Santorini during May 2026 with 985 Reviews

Get a customized trip to Santorini in May 2026

Mainland Greece And Islands - May 2026

Greek Island Hopping - May 2026

Athens, Mykonos & Santorini - May 2026

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

Best of Greece - May 2026

Greek Island Hopper - May 2026

Treasures of Greece & The Islands - May 2026

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

Greece: Walking in the Greek Islands - May 2026

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

Greek Island Hopping: Paros, Ios & Santorini Sunsets - May 2026

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

Dubrovnik to Santorini - May 2026

Premium Greece Cyclades Islands - May 2026

Page 3 of 89 Trips in Santorini during May 2026 with 985 Reviews

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 89 Trips in Santorini during May 2026 with 985 Reviews

Get a customized trip to Santorini in May 2026

Page 3 of 89 Trips in Santorini during May 2026 with 985 Reviews