10 Best Syros Multiday Tours in May 2026

Super Sales

Sail Greece: Mykonos to Santorini - May 2026

(1 review )

No booking fees

Best price guaranteed

This was the absolute best trip ever. Ive traveled many times. I have to say this was one of the best experiences and adventures of all. Our skipper, Rita was simply amazing. The best! Wonderful skipper, skilled sailor, knowledgeable, so friendly, helpful, genuinely caring of her boat mates. Shes a dream to sail with! If anyone sails, Id highly recommend requesting her.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin, Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Mykonos, Santorini, Syros, Naxos

Mykonos, Santorini, Syros, Naxos, Cyclades, Amorgos, Ios

Duration8 days

From

USD 1,765

USD 1,712

Saving

USD 53

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Best Seller

Super Sales

Athens to Santorini - May 2026

(1 review )

No booking fees

Best price guaranteed

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

Duration8 days

From

USD 2,850

USD 2,765

Saving

USD 86

Instant book available

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Super Sales

Greece Sailing Adventure: Cyclades Islands - May 2026

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Best price guaranteed

Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Hotel, Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Santorini, Amorgos, Small Cyclad

Santorini, Amorgos, Small Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros

Duration10 days

From

USD 2,310

USD 2,241

Saving

USD 69

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Greek Island Wanderer - May 2026

4.7

(35 reviews )

No booking fees

Best price guaranteed

The Greek Island wanderer through the Cyclades was fantastic- the leader was flexible and positive all the way through - he really looked after our group. I can’t wait to do another trip with Explore

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Athens, Naxos, Santorini, Syros

Athens, Naxos, Santorini, Syros, Paros, Drios

Duration14 days

From

USD 2,960

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Super Sales

Best of Greece - May 2026

(1 review )

No booking fees

Best price guaranteed

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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Super Sales

Dubrovnik to Santorini - May 2026

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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 6,800

USD 6,596

Saving

USD 204

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Super Sales

Highlights of Turkey & the Greek Islands - May 2026

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Best price guaranteed

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 5,445

USD 5,282

Saving

USD 163

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All Syros Tours in May 2026

7 Trips in Syros during May 2026 with 38 Reviews