10 Best Greece Multiday Tours in May 2026

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Best of Greece - May 2026

(3 reviews )

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Sophia, our tour guide, MADE this trip as amazing as it was! Best time in Greece

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-75 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini, Ios

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Duration10 days

From

USD 3,371

USD 2,023

Saving

USD 1,348

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Athens+2 Island Explorer - May 2026

4.5

(2 reviews )

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Brilliant tour, amazing people, awesome tour leader!! Definitely would do again!!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-75 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos

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Duration7 days

From

USD 2,641

USD 1,585

Saving

USD 1,056

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Sail Greece: Santorini to Mykonos - May 2026

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Dreaming of crystal-clear waters, whitewashed villages, historical ruins, lively Greek culture and deliciously fresh cuisine straight from the sea? Then sail from Santorini to Mykonos on this eight-day boat trip in Greece. Spend blissed-out days under sun drenched skies enjoying the best of the Greek Islands, including Santorini, Ios, Amorgos, the Small Cyclades, Naxos and Mykonos. Watch the sunset, explore olive groves, feast on fresh food and wine and fall asleep to the gentle rocking of your yacht every night.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Mykonos, Santorini, Ios, Amorgos

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

Duration8 days

From

USD 1,690

USD 1,639

Saving

USD 51

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Sail Greece: Mykonos to Santorini - May 2026

(1 review )

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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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Greece Sailing Adventure: Cyclades Islands - May 2026

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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, Ios, Amorgos, Small C

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

Duration10 days

From

USD 2,310

USD 2,241

Saving

USD 69

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Sailing Greece - Santorini To Mykonos - May 2026

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Sailing Greece - Santorini to Mykonos - May 2026

(4 reviews )

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I loved the opportunity to undertake a yacht sailing voyage for a week in safe hands, with good company and a good variety of interesting land excursions. For me the highlight was the nights a5 anchor in isolated bays with the opportunity to dive off the boat into crystal blue waters.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Mykonos, Santorini, Folegandros

Mykonos, Santorini, Folegandros, Sifnos

Duration8 days

From

USD 1,679

USD 1,629

Saving

USD 50

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Sailing Greece - Santorini to Santorini - May 2026

(6 reviews )

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A lot of togetherness. If you?re going on this trip, be prepared for close quarters, shared duties, and a lot of time together. If that?s what you signed up for, then expect a fabulous journey to the Cyclades in Greece.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Santorini, Ios, Mykonos, Syros

Duration10 days

From

USD 2,349

USD 2,279

Saving

USD 70

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Sailing Greece - Athens to Mykonos - May 2026

4.8

(5 reviews )

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We had a fantastic time and enjoyed having access to some of the smaller, less travelled islands. We had experiences we wouldn't have had on a self-guided trip and the opportunity to meet other travellers (I actually added a week of travel in another country with a friend I met on the boat!). This was a cool way to experience Greece and I am excited to try other G Adventures tours in the future!

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Athens, Mykonos, Syros, Kea

Duration8 days

From

USD 1,649

USD 1,600

Saving

USD 49

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Sailing Greece - Mykonos to Athens - May 2026

(4 reviews )

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Amazing experience, Herman our CEO made it exceptional, as did the beautiful weather and incredible blue waters.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Athens, Mykonos, Syros, Northern Cyclades

Duration8 days

From

USD 1,649

USD 1,600

Saving

USD 49

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Sailing Greece - Mykonos to Santorini - May 2026

(4 reviews )

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This was a great trip and has made me want to explore Greece further. We didn?t have much wind which had a lot of upsides actually, the group we went with were amazing and our captain Erwin was helpful, practical and entertaining. I would recommend bringing a driving licences so more exploration of the islands could be done. I?m not sure it would be a comfortable trip if you had to share a tiny cabin with a stranger, or didn?t like swimming, but my partner and I had an awesome time. Thanks all!

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Mykonos, Santorini, Naxos, Paros

Mykonos, Santorini, Naxos, Paros, Folegandros

Duration8 days

From

USD 1,699

USD 1,648

Saving

USD 51

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Ionian Islands Bike & Boat - May 2026

4.9

(7 reviews )

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Excellent trip, fabulous guides, well-organized program and excellent food onboard.

Bicycle tours

Tour Type

Group Tour

Accommodation

Yacht Cabin, Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Athens, Corfu, Nidri, Kefalonia

Athens, Corfu, Nidri, Kefalonia, Ithaca

Duration8 days

From

USD 3,390

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Greek Islands Bike & Boat - May 2026

4.6

(7 reviews )

No booking fees

Best price guaranteed

We thoroughly enjoyed our adventure. The crew was stellar, the food was amazing and fresh, the seas were smooth so we had no issues with motion sickness. The ship was beautiful and clean. The only issue we encountered was the fumes from the engine room, since our cabin was adjacent to it. It was the strongest on the first night after being in port.

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

18-99 yrs

Operated in

english

Destinations

Athens, Port Of Piraeus, Kythnos

Athens, Port Of Piraeus, Kythnos, Sifnos, Kea

Duration8 days

From

USD 5,290

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Sailing Greece - Athens to Santorini - May 2026

4.8

(4 reviews )

No booking fees

Best price guaranteed

Pseudo (only sailed a bit because the main mast was broken) sailing the Aegian islands was a wonderful way to visit the area and meet new people. My overall experience other than a few things regarding cleanliness and upkeep of the vessel (sails, stains, smells) was excellent and I am left with many wonderful memories.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Athens, Santorini, Naxos, Syros

Athens, Santorini, Naxos, Syros, Kea, Mykonos

Duration15 days

From

USD 3,249

USD 3,152

Saving

USD 97

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Sailing Greece - Santorini to Athens - May 2026

4.5

(4 reviews )

No booking fees

Best price guaranteed

Great way to island hop the Greek islands. Beautiful places, great companionship with other passengers. Everyone chipped in to make lunches, shop for food and clean up etc. Great relaxing trip! CEO on the first week of our trip was exceptional.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Athens, Santorini, Kea, Folegand

Athens, Santorini, Kea, Folegandros, Sifnos, Mykonos, Kythnos

Duration15 days

From

USD 3,229

USD 3,132

Saving

USD 97

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Combine Greece in May with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Greece

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Alternatively, explore tours that are exclusively just France and Greece, Germany and Greece or England and Greece.

All Greece Tours in May 2026

21 Trips in Greece during May 2026 with 67 Reviews

See Greece tours by duration

Best of Greece - May 2026

Athens+2 Island Explorer - May 2026

Sail Greece: Santorini to Mykonos - May 2026

Sail Greece: Mykonos to Santorini - May 2026

Greece Sailing Adventure: Cyclades Islands - May 2026

Sailing Greece - Santorini to Mykonos - May 2026

Sailing Greece - Santorini to Santorini - May 2026

Sailing Greece - Athens to Mykonos - May 2026

Sailing Greece - Mykonos to Athens - May 2026

Sailing Greece - Mykonos to Santorini - May 2026

Ionian Islands Bike & Boat - May 2026

Greek Islands Bike & Boat - May 2026

Sailing Greece - Athens to Santorini - May 2026

Sailing Greece - Santorini to Athens - May 2026

21 Trips in Greece during May 2026 with 67 Reviews

Combine Greece in May with Nearby Countries for an Unforgettable Trip

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All Greece Tours in May 2026

21 Trips in Greece during May 2026 with 67 Reviews

See Greece tours by duration

21 Trips in Greece during May 2026 with 67 Reviews