10 Best Santorini Multiday Tours in May 2027

Greek Island Hopping - May 2027

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

View Tour

Super Sales

Greek Island Hopping: Paros, Ios & Santorini Sunsets - May 2027

(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

View Tour

Super Sales

Premium Greece in Depth - May 2027

No booking fees

Best price guaranteed

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

View Tour

Super Sales

Premium Greece Cyclades Islands - May 2027

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 4,030

USD 3,909

Saving

USD 121

View Tour

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

4.5

(50 reviews )

No booking fees

Best price guaranteed

All great, except Collette was not great with the communication for the Istanbul extension. The Hagia Sofia visit was cancelled by Collette with no explanation. So our group booked it ourselves. But on arrival it was part of our Collette tour. Not sure what happened.

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

Duration16 days

From

USD 5,199

USD 4,999

Saving

USD 200

View Tour

London to Santorini - May 2027

(2 reviews )

No booking fees

Best price guaranteed

Loved the fast paced trip and now many nights we were able to go out. the trip managers were also incredible and very knowledgeable

City sightseeing

Tour Type

Group Tour

Accommodation

Hostel, Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Paris, London, Santorini, Venice

Paris, London, Santorini, Venice, Florence, Rome, Athens, Mykonos, Paros, Beaujolais, Barcelona, French Riviera

Duration24 days

From

USD 4,295

View Tour

Athens to Santorini Island Hopping - May 2027

4.9

(19 reviews )

No booking fees

Best price guaranteed

Fantastic way to see some of the main islands in Greece

Sightseeing ToursBeach

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Athens, Santorini, Mykonos, Paros

Duration8 days

From

USD 1,315

View Tour

London to Athens with Greek Island Hopping - May 2027

(3 reviews )

No booking fees

Best price guaranteed

Amazing experience!! met the best people and had the best time! London to Athens was very jam packed and exciting, the greek island hopping was relaxing but also had lots of parties so it was a great way to end the trip!!

Sightseeing ToursBeach

Tour Type

Group Tour

Accommodation

Hostel, Hotel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

London, Athens, Paris, Venice, F

London, Athens, Paris, Venice, Florence, Rome, Mykonos, Paros, Santorini, Ios, Beaujolais, Barcelona, French Riviera

Duration27 days

From

USD 4,675

View Tour

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

4.7

(176 reviews )

No booking fees

Best price guaranteed

Our tour guide was very knowledgeable and made the history interesting. Very personable and had celebrated the birthdays that happened on the trip. The included meals were delicious and the cooking demo the best I've ever attended. Hotels were nice to very nice. The 3-night stays we're fantastic! I would definitely recommend this trip!!!

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

View Tour

All Santorini Tours in May 2027

9 Trips in Santorini during May 2027 with 296 Reviews

Get a customized trip to Santorini in May 2027

9 Trips in Santorini during May 2027 with 296 Reviews

Greek Island Hopping - May 2027

Greek Island Hopping: Paros, Ios & Santorini Sunsets - 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

London to Santorini - May 2027

Athens to Santorini Island Hopping - May 2027

London to Athens with Greek Island Hopping - 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

9 Trips in Santorini during May 2027 with 296 Reviews

Get a customized trip to Santorini in May 2027

9 Trips in Santorini during May 2027 with 296 Reviews