10 Best Greece Multiday Tours in May 2026

Sailing Greece - Mykonos To Mykonos - May 2026

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Sailing Greece - Mykonos to Mykonos - May 2026

(3 reviews )

No booking fees

Best price guaranteed

Have traveled with g @dventures 4 times. Once with a group of 3 friends, twice with my cousin, and solo. Every time has been amazing. Tour itineraries are accurate. Small groups have united quickly. I am very pleased with all of my adventures. Sailing the Greek isles is a dream come true. The captain and boat were above expectations Freedom of itinerary made everyday a new experience Keep up the excellent work!

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

16-100 yrs

Operated in

english

Destinations

Mykonos, Syros, Santorini, Ios

27% OFF TODAY

Duration10 days

From

USD 2,299

USD 1,672

Saving

USD 627

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Greece: Walking in the Greek Islands - May 2026

(4 reviews )

No booking fees

Best price guaranteed

I had an exceptional, once-in-a-lifetime and unique experience on the G Adventures Walking in the Greek Islands tour. I loved the experience of not being the 'Chief Experience Officer' of the holiday for once, and was truely able to relax and enjoy myself. While it was a fantastic itinerary full of interesting and enjoyable activities, it was also the people that made it special.

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 3,999

USD 3,879

Saving

USD 120

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Greece Sailing Adventure: Corfu To Kefalonia - May 2026

23% OFF TODAY

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Greece Sailing Adventure: Corfu to Kefalonia - May 2026

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Come aboard and sail through some of the most beautiful Greek islands in the Ionian Sea. On this eight-day trip from Corfu to Kefalonia, you’ll journey through secluded coastlines, private islands, rolling hills and orchards, Venetian architecture, warm tavernas and some of the world’s cleanest waters. Each day, you’ll go for a swim in bright blue bays, watch the sunset on the deck of your sailing boat and spend the night on the town, exploring everything these islands have to offer. Stop in Paxos, Antipaxos, Lefkadas, Meganisi, Ithaca, Atokos, Kastos and Kalamos and walk their winding shores and white sands, chill on their comfortable beaches and discover coves that are only seen by boat.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Corfu, Kefalonia, Paxos, Lefkada

Corfu, Kefalonia, Paxos, Lefkadas, Ithaca

23% OFF TODAY

Duration8 days

From

USD 2,535

USD 1,955

Saving

USD 580

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Wonders of Athens Mykonos Santorini and Crete - May 2026

Trip customizable

Best price guaranteed

This trip will guide you through the most magnificent islands and cosmopolitan cities in Greece! Begin your journey in Athens, where you will see breathtaking views of the famous Acropolis in the heart of the city. Take a ferry to Mykonos, the bustling party island, famous for its delicious Mediterranean cuisine, exhilarating nightlife scene, and romantic resorts. Sail to Santorini for a stop on this magical island with beautiful beaches, world-class restaurants, and breathtaking views. Next, you will explore Heraklion on the island of Crete, boasting fascinating remnants from brilliant ancient civilizations. Explore the sandy beaches and traditional villages of these sun-drenched islands as you lose yourself in the vast and varied landscapes and ancient treasures. Catch a flight to Athens where you will end your tour of the Greek Islands!

Cultural, religious and historic sites

Tour Type

Independent Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

English

Destinations

Athens, Mykonos, Santorini, Heraklion

Duration10 days

From

USD 2,414

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Greece Sailing Adventure: Kefalonia to Corfu - May 2026

No booking fees

Best price guaranteed

Take a relaxing sailing trip through some of the most beautiful Greek islands in the Ionian Sea. On this eight-day trip from Kefalonia to Corfu, you’ll journey to some secluded coastlines, private islands, rolling hills and orchards, Venetian architecture, warm and inviting tavernas and some of the world’s most transparent waters. Each day, swim in secluded bays, watch the sunset on the deck of your group’s sailing boat and spend the night on the town, exploring everything these islands offer. Explore Atokos, Kastos, Kalamos, Ithaca, Meganisi, Lefkadas, Paxos and Antipaxos, and their winding shores, white sands, comfortable beaches and coves that are only seen by boat.

Sailing, yachting and motor boating

Tour Type

Small Group Tour

Accommodation

Yacht Cabin

Age Range

15-99 yrs

Operated in

english

Destinations

Corfu, Kefalonia, Ithaca, Megani

Corfu, Kefalonia, Ithaca, Meganisi, Lefkadas, Paxos

Duration8 days

From

USD 2,450

USD 2,377

Saving

USD 74

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5% OFF TODAY

Gems of Greece: Athens, Naxos & Crete - May 2026

No booking fees

Best price guaranteed

On an immersive journey through Greece, discover its ancient roots, iconic landmarks, and welcoming culture, from Athens to the islands of Naxos and Crete. Visit the iconic Acropolis and get to know Athens’ lively neighborhoods. Ferry to Naxos and dive into Greek island life and culture during a three-night stay. Explore Crete’s treasures from Heraklion and Chania, including Knossos Palace, the pottery village of Margarites, Chania’s old Venetian Harbor, and more. Delve into the traditions, flavors, and history of Greece, exploring unique corners of the country and meeting locals along the way.

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Athens, Chania, Naxos, Heraklion

5% OFF TODAY

Duration14 days

From

USD 5,349

USD 5,099

Saving

USD 250

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Highlights of the Greek Islands - May 2026

4.7

(9 reviews )

No booking fees

Best price guaranteed

Our tour was first rate, but what really made the difference was our leader, Charlotte! There were 15 of us in total. And throughout the week, she made sure that every single member of our group was having fun! Both of the walks were fantastic and the scenery was unparalleled! Although Santorini was beautiful, Naxos was a wonderful surprise. Knowing so little about it before the trip, it was such fun to explore and discover. The Explore app is a great new addition, putting our itinerary right at our fingertips. But there were some discrepancies with timing when it came to the ferries. None of us objected to the lengthy ferry ride from Athens to Naxos. But the itinerary said it was 5 hours when the reality was 7. We would have like better information upfront. Also, skip the hotel dinner at Santorini. There are too many wonderful restaurants to try! We don't need a mediocre buffet dinner. We all would have preferred a cocktail or drinks gathering, or nothing at all. Overall, this was my second trip with Explore and I am now confident that there will be more. This was such a lovely week filled with great experiences and wonderful people. I want to thank the Explore team for the great work that they do with their tour leaders. Again, Charlotte is a star! She is to be commended for her stellar job. Every member of our group adored her! She was so attentive and so in tune with both us and the locals that we interacted with. We felt so well taken care of.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Athens, Santorini, Naxos, Apiranthos

Duration8 days

From

USD 2,350

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All Greece Tours in May 2026

Page 2 of 21 Trips in Greece during May 2026 with 67 Reviews

See Greece tours by duration

Sailing Greece - Mykonos to Mykonos - May 2026

Greece: Walking in the Greek Islands - May 2026

Greece Sailing Adventure: Corfu to Kefalonia - May 2026

Wonders of Athens Mykonos Santorini and Crete - May 2026

Greece Sailing Adventure: Kefalonia to Corfu - May 2026

Gems of Greece: Athens, Naxos & Crete - May 2026

Highlights of the Greek Islands - May 2026

Page 2 of 21 Trips in Greece during May 2026 with 67 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 Greece Tours in May 2026

Page 2 of 21 Trips in Greece during May 2026 with 67 Reviews

See Greece tours by duration

Sailing Greece - Mykonos to Mykonos - May 2026

Greece: Walking in the Greek Islands - May 2026

Greece Sailing Adventure: Corfu to Kefalonia - May 2026

Wonders of Athens Mykonos Santorini and Crete - May 2026

Greece Sailing Adventure: Kefalonia to Corfu - May 2026

Gems of Greece: Athens, Naxos & Crete - May 2026

Highlights of the Greek Islands - May 2026

Page 2 of 21 Trips in Greece during May 2026 with 67 Reviews