10 Best Santorini Multiday Tours in October 2027

Get a customized trip to Santorini in October 2027

Plan a multi-country or regional adventure across Santorini in October 2027, with help from a local expert.

Canan KaraarslanTravel Expert in Egypt, Greece, Jordan, Morocco & Turkey
Julia KourafaTravel Expert in Greece
Angela GianniotiTravel Expert in Greece
Kate PolitiTravel Expert in England, France, Germany, Greece & Slovenia
Elena KyrimiTravel Expert in Greece & Italy

Start planning your Trip

Recommended by

Super Sales

Sail Greece: Mykonos to Santorini - October 2027

(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

View Tour

Super Sales

Sail Greece: Santorini to Mykonos - October 2027

No booking fees

Best price guaranteed

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, Small C

Mykonos, Santorini, Ios, Small Cyclades, Amorgos, Naxos

Duration8 days

From

USD 1,690

USD 1,639

Saving

USD 51

View Tour

Super Sales

Best of Greece - October 2027

4.9

(11 reviews )

No booking fees

Best price guaranteed

Loved it and so glad I went. Without this planned itinerary I would have missed half the things.

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

Duration15 days

From

USD 3,899

USD 3,782

Saving

USD 117

View Tour

Best Seller

Super Sales

Athens to Santorini - October 2027

(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

View Tour

Super Sales

Best of Greece - October 2027

(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

View Tour

Super Sales

Highlights of the Greek Islands - October 2027

(9 reviews )

No booking fees

Best price guaranteed

First of all, Vasilis is a great tour director. He is very friendly and supportive. By communicating with us either in the group chat and face to face, he made it easy for everyone. The islands included in this tour are different and the activities either included or optional are very well suited for each island. I have made fond memories for life. Thank you G Adventure.

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

Duration8 days

From

USD 2,199

USD 2,133

Saving

USD 66

View Tour

Super Sales

Greek Island Hopping: Paros, Ios & Santorini Sunsets - October 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

Dubrovnik to Santorini - October 2027

No booking fees

Best price guaranteed

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

View Tour

Super Sales

Premium Greece in Depth - October 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 - October 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

Super Sales

Highlights of Turkey & the Greek Islands - October 2027

No booking fees

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

View Tour

Super Sales

Premium Turkey & The Cyclades Islands in Depth - October 2027

No booking fees

Best price guaranteed

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 11,130

USD 10,796

Saving

USD 334

View Tour

Super Sales

Solo-ish Greece - October 2027

(4 reviews )

No booking fees

Best price guaranteed

It was wonderful to experience Greece with others without feeling like I should find a friend to travel with. Our CEO’s enthusiasm about the culture was contagious. Thanks for creating an active vacation experience!

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

View Tour

Super Sales

Crete & Santorini Discovery - October 2027

(4 reviews )

No booking fees

Best price guaranteed

Lovely trip to Crete, showing the highlights of the island. It was nice to visit the smaller villages that I wouldn’t have known of. Beautiful scenery, clear blue water, and nice pebble beaches. The CEO Sakis was excellent and helped navigate us throughout the trip and recommended some really nice restaurants and bakeries. Ending in Santorini to see a different island with completely different vibe was a good way to end the trip.

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

Duration8 days

From

USD 1,899

USD 1,842

Saving

USD 57

View Tour

All Santorini Tours in October 2027

14 Trips in Santorini during October 2027 with 37 Reviews

Get a customized trip to Santorini in October 2027

14 Trips in Santorini during October 2027 with 37 Reviews

Sail Greece: Mykonos to Santorini - October 2027

Sail Greece: Santorini to Mykonos - October 2027

Best of Greece - October 2027

Athens to Santorini - October 2027

Best of Greece - October 2027

Highlights of the Greek Islands - October 2027

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

Dubrovnik to Santorini - October 2027

Premium Greece in Depth - October 2027

Premium Greece Cyclades Islands - October 2027

Highlights of Turkey & the Greek Islands - October 2027

Premium Turkey & The Cyclades Islands in Depth - October 2027

Solo-ish Greece - October 2027

Crete & Santorini Discovery - October 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 October 2027

14 Trips in Santorini during October 2027 with 37 Reviews

Get a customized trip to Santorini in October 2027

14 Trips in Santorini during October 2027 with 37 Reviews