10 Best Santorini Multiday Tours in May 2027

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Best of Greece - May 2027

4.9

(7 reviews )

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Overall, this was one of the best trips ever. One suggestion I have, in the past the tour stared off with a tipping kitty that the CEO would collect at the beginning of the tour. Please bring the back. It is very confusing when the people on the tour must figure out how much to tip the drivers and other axillary staff. Please bring it back!!!!!!

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Athens, Santorini, Delphi, Meteo

Athens, Santorini, Delphi, Meteora, Loutro, Irakleion, Nafplion, Chania, Agia Roumeli

27% OFF TODAY

Duration15 days

From

USD 4,299

USD 3,127

Saving

USD 1,172

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18% OFF TODAY

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Athens to Santorini - May 2027

(1 review )

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Embark on a tour through the Aegean Sea, taking local ferries around the Cyclades Islands. Indulge in a little island hopping and take the time to uncover remote ruins, gorgeous beaches and outstanding scenery. Travel from the ancient capital of Athens all the way to the spectacular natural wonders on the island of Santorini on this wonderful Greek adventure.

CruiseBeach

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Athens, Santorini, Syros, Mykono

Athens, Santorini, Syros, Mykonos, Delos

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Duration8 days

From

USD 2,580

USD 2,127

Saving

USD 453

Instant book available

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Best of Greece - May 2027

(1 review )

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Experienced a lot, learned a lot and travelled with some interesting people. A nice balance of activities with appropriate down time.

Cruise

Tour Type

Small Group Tour

Accommodation

Hotel, Camping

Age Range

15-99 yrs

Operated in

english

Destinations

Athens, Santorini, Syros, Mykono

Athens, Santorini, Syros, Mykonos, Thessaloniki, Kalambaka, Delphi

Duration15 days

From

USD 4,845

USD 4,700

Saving

USD 145

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Highlights Of The Greek Islands - May 2027

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Highlights of the Greek Islands - May 2027

(5 reviews )

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It was the most amazing experience of my life, to date! I love that everything was pretty much planned for me. I didn't have to worry about details. We were given a few options on activities, which was perfect. I would highly recommend anyone doing a trip with G and I can't wait for another one myself.

Sightseeing ToursBeach

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Athens, Santorini, Tinos, Mykono

Athens, Santorini, Tinos, Mykonos, Naxos

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Duration8 days

From

USD 2,149

USD 1,563

Saving

USD 586

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Dubrovnik to Santorini - May 2027

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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 4,955

USD 4,806

Saving

USD 149

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Premium Greece in Depth - May 2027

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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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Premium Greece Cyclades Islands - May 2027

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Premium Greece Cyclades Islands - May 2027

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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

27% OFF TODAY

Duration9 days

From

USD 5,105

USD 3,714

Saving

USD 1,391

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7% OFF TODAY

Exploring Greece and Its Islands featuring Classical Greece, Mykonos & Santorini - May 2027

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Discover the magnificent ruins of ancient Greece and bask in the brilliance of the Mediterranean. This comprehensive journey explores Greece's most important ancient monuments, including the famed Temple of Zeus, the archaeological site of Olympia and ancient artifacts of Delphi. Explore Athens on a comprehensive tour of the incredible Acropolis. Visit a local farm in the countryside to see how olive oil and wine are produced. Learn how to cook traditional Mediterranean cuisine during a cooking demonstration. Wander the winding streets, vineyards, marketplaces and beaches of Mykonos and Santorini. Explore the excavations of the ancient city at Akrotiri, the most important prehistoric settlement found anywhere in the Eastern Mediterranean. Learn the history of this fascinating country from local experts on guided tours of Athens, Metéora, Delphi, and Olympia. Throughout your journey, experience the iconic sights of Greece's Classical age with ample time to explore on your own.

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

7% OFF TODAY

Duration16 days

From

USD 5,299

USD 4,949

Saving

USD 350

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Highlights of Turkey & the Greek Islands - May 2027

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Journey through ancient ruins and Greek Ottoman villages on this 15-day island adventure from Turkey to Greece. Visit ANZAC Cove in Canakkale, join your local leader on a walking tour of Istanbul and learn about the archaeological and mythological sites in the Greek Islands like Delos. Discover the ruins of the ancient city of Ephesus, explore the small coves outside Ermoupolis and indulge in traditional dishes and local wine at an authentic Greek Ottoman village in Sirince.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Istanbul, Syros, Mykonos, Santor

Istanbul, Syros, Mykonos, Santorini, Kusadasi, Ephesus, Cappadocia, Athens

Duration15 days

From

USD 4,870

USD 4,724

Saving

USD 146

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Premium Turkey & The Cyclades Islands in Depth - May 2027

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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 9,755

USD 9,462

Saving

USD 293

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Solo-ish Greece - May 2027

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Island hopping in Greece—it’s the dream, right? Picture sun-kissed beaches, whitewashed villages, and epic sunsets over the Mediterranean. On this nine-day adventure from Athens to Santorini, you'll experience it all and a whole lot more. Start by uncovering ancient history at the Acropolis and Parthenon, then wander the charming streets of Mykonos and Naxos. Make new friends while learning Greek cuisine at a cooking class in Athens, and indulge in fresh local flavours on a food tour in Tinos. End your journey in Santorini, strolling along the volcanic caldera and soaking up those iconic views.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-100 yrs

Operated in

english

Destinations

Athens, Santorini, Tinos, Mykono

Athens, Santorini, Tinos, Mykonos, Naxos

Duration9 days

From

USD 2,699

USD 2,618

Saving

USD 81

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27% OFF TODAY

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Crete & Santorini Discovery - May 2027

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Got eight days? Then you've got all the time you need to soak up the soul of Greece (and some sunrays too obviously). Explore the intricate remains of Europe’s oldest city and learn of the once thriving civilization at the Palace of Knossos. Sail past breathtaking Aegean vistas on an optional sunset cruise from Oia and enjoy Crete’s most stunning natural gorge on the Samaria Gorge hike. Get ready to witness unparalleled beauty on an unforgettable escape into paradise.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Santorini, Chania, Agia Roumeli

Santorini, Chania, Agia Roumeli, Loutro, Irakleion

27% OFF TODAY

Duration8 days

From

USD 1,899

USD 1,381

Saving

USD 518

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One Week in the Greek Islands - May 2027

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Best price guaranteed

Calling all nature lovers, beachside loungers and avid explorers – this eight-day adventure will take you to all the hotspots throughout the famous Greek Islands. Explore an ancient citadel in Athens, then take a ferry to Paros in the Aegean Sea. See traditional villages, natural swimming coves and maybe even take a ride to the sister island Antiparos for a local bite. Head to the village of Lefkes and explore the scenic olive-grove locale before a lunch of moussaka, dolmas and Greek salad. Head to Ios – a hub of vibrant nightlife and countless beaches to kick back on – and watch the sunset over an iconic city with some new mates. End it all in Santorini, where you can hike off the refreshing glass (or glasses) of the country’s most popular wine and sit down for another epic sunset. This is the perfect way to forge new friendships!

Adventure

Tour Type

Small Group Tour

Accommodation

Hotel, Hostel

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Santorini, Paros, Ios

Duration8 days

From

USD 1,505

USD 1,460

Saving

USD 45

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Greece Island Hopper featuring Athens, Mykonos and Santorini - May 2027

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Best price guaranteed

In Greece, discover a place where age-old legends and monuments intertwine with warm sunshine and island-style living. Tour Athens with a local guide. Explore the Acropolis, home to the famous Parthenon and the city’s best lookout. Enjoy three days at leisure on the island of Mykonos, an Aegean paradise of sandy beaches and bustling energy. Uncover the past at the excavation site of Akrotiri. Make the most of a free day on the picture-perfect island of Santorini. From to the ruins of Athens to the bright rooftops of Mykonos and Santorini – embrace the country at its best.

Chill outBeach Holidays

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini

Duration11 days

From

USD 3,599

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All Santorini Tours in May 2027

16 Trips in Santorini during May 2027 with 14 Reviews

16 Trips in Santorini during May 2027 with 14 Reviews

Best of Greece - May 2027

Athens to Santorini - May 2027

Best of Greece - May 2027

Highlights of the Greek Islands - May 2027

Dubrovnik to Santorini - May 2027

Premium Greece in Depth - May 2027

Premium Greece Cyclades Islands - May 2027

Exploring Greece and Its Islands featuring Classical Greece, Mykonos & Santorini - May 2027

Highlights of Turkey & the Greek Islands - May 2027

Premium Turkey & The Cyclades Islands in Depth - May 2027

Solo-ish Greece - May 2027

Crete & Santorini Discovery - May 2027

One Week in the Greek Islands - May 2027

Greece Island Hopper featuring Athens, Mykonos and Santorini - May 2027

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 2027

16 Trips in Santorini during May 2027 with 14 Reviews

16 Trips in Santorini during May 2027 with 14 Reviews