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ToursEuropeGreek IslandsGreek Islands Sailing Trips & Packages

Top Greek Islands Sailing Trips & Packages In 2025/2026

Our 11 most popular Greek Islands Sailing Trips & Packages trips. Compare tour itineraries from 7 tour companies. 62 reviews.

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All Greek Islands Sailing Trips & Packages, expedition cruises, self guided adventures and vacation packages. Find the best guided and expert planned vacation and holiday packages. Read more about Greek Islands Sailing Trips & Packages

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Small Group Greek Islands Sailing Trips & Packages Tours

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Small Group Greek Islands Sailing Trips & Packages ToursSmall Group Greek Islands Sailing Trips & Packages Tours2 trips >
Greek Islands Sailing Adventure
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Trip Details

Greek Islands Sailing Adventure

By Trails Beyond
none
5/5 Excellent
46 reviews
Small Group Tour
8 days From$1,280

Highlights

  • Explore the historical, traditional villages of Mount Mainalos (Dimitsana, Stemnitsa, Lagadia & Karytaina) & learn more about the significant culture and history of the area
  • Hike through the imposing Lousios gorge and visit the unique monasteries of Prodromou and Philosophou
  • Enjoy rafting in one of Greece’s most impressive rivers, Lousios!
  • Visit the open-air Water Power museum and find out how water was used in the pre-industrial local societies for the production of various goods
  • Taste the delicious local cuisine of mountainous Arcadia
8 days From$1,280
Trip dates & details
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Sailing & Hiking in the Cyclades 8 days
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Trip Details

Sailing & Hiking in the Cyclades 8 days

By Personality Journeys
none
5/5 Excellent
5 reviews
Small Group Tour
8 days From$1,112

Highlights

  • Visit to Kea. Fertile and green, Kea is hikers’s paradise
  • Hike around Loutra in Kythnos, where you will discover hidden centuries-old castles
  • Explore the western part of Syros hiking
  • Visit to Serifos island, an integral part of Greek mythology
  • Visit to island of Kythnos from where you can admire this unique natural phenomenon
Show more
8 days From$1,112
Trip dates & details
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Trip Reviews

B

Bruce

Nov 2016

Written on
Yolo Yachting - Santorini to Mykonosby Sail in Greece

I would suggest it to me friends

We joined Sail in Greece end of August. We did the yachting tour with Christos ( our skipper). We were on board 9 people and majority were kiwis... I had a bit of ha...

M

Micheal

Sep 2016

Written on
Yolo Yachting - Santorini to Mykonosby Sail in Greece

Lovely week!

What a week! We visited what many people believe the BEST islands in the world! Ios was my favorite and def i will go back some day. The only complain i can find is ...

V

Vitoria

Sep 2016

Written on
Yolo Yachting - Santorini to Mykonosby Sail in Greece

The Greek islands were very windy!

The Greek islands were very windy! I did not do much of a research before and when i got there i realized that the weather can be crazy! We were lucky and 2 of the d...

C

Cons

Sep 2016

Written on
Yolo Yachting - Santorini to Mykonosby Sail in Greece

We enjoyed the activities.

Even if we had rough weather and missed a couple of island on the way, George and Ben managed to have a back up plan and we enjoyed the activities. Ios was by far th...

K

Kiko

Sep 2016

Written on
Yolo Yachting - Santorini to Mykonosby Sail in Greece

We joined the yolo yachting tour

We joined the yolo yachting tour. Christos our skipper was great and welcoming all time. Our tour manager George, was a bit rude at times and we were dealing with Be...

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