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Greek Islands Sailing Tours & Trips

10 Greek Islands Sailing trips. Tours from 6 tour companies. 62 reviews.

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10 Trips match your criteria (1 - 10 shown)

Yolo Yachting - Mykonos to Santorini
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Yolo Yachting - Mykonos to Santorini

By Sail in Greece
preferred
3.9/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-36%$529
8 days From$339
Price updated 1 year+ ago

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Sailing & Hiking in the Cyclades 8 days
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Sailing & Hiking in the Cyclades 8 days

By Personality Journeys
none
5/5 Excellent
5 reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Strenuous
Trip pace
Balanced schedule

Visits

Athens

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

Themes

Hiking & Walking, Sailing

What travelers are saying

"Dimitris was everything we could have looked for in a travel agent. Following the parameters we laid out for him, he provided us with the absolute best options for our travels. He was both honest and patient with us, and made sure we took as much time as we needed to finalize a trip that felt right for our group. Dimitris informed us on everything that was going on throughout our booking and travel process, so there were no surprises along the way. He answered every question we had and made sure we were prepared when we arrived in Athens. Andreas went above and beyond in his role as our skipper for the week. He was patient and thoughtful with our group, and put so much effort into making sure we had the best trip possible. We felt very safe and protected throughout all of our travels, and were taken to some of the most incredible place – places that weren’t even on our initial itinerary. Andreas’ expertise in his craft and his companionate demeanor are the reasons our trip was as fantastic as it was. He exceeded all of our expectations and genuinely made this trip one of the best of our lives. Thank you, Dimitris and Andreas, for giving us a week we will never forget! We can honestly say we would not have had the same experience if it wasn't for all of your help and consideration."

Trip dates & details
Save this trip to your favorites or other list
-17%$1,344
8 days From$1,112
Price updated 1 year+ ago

Health Safety

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YOLO CRUISE - Mykonos to Santorini
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YOLO CRUISE - Mykonos to Santorini

By Sail in Greece
preferred
3.2/5 Average
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing.
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

18 - 30's, 50 plus, Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-42%$516
8 days From$299
Price updated 1 year+ ago

Health Safety

More
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Harmony Cruises
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Harmony Cruises

By Sail in Greece
preferred
4.6/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Visits

Acropolis, Temple of Zeus, Venetian Lagoon

Highlights

  • Explore old cities of Athens over 3,400 years of history
  • Enjoy general city navigation and history, to philosophy, architecture
  • Enjoy all the meze and traditional Greek music to match your classic toga outfit.
  • Explore ancient town of Ermioni

Themes

Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-26%$494
8 days From$366
Price updated 1 year+ ago

Health Safety

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Yolo Yachting - Santorini to Mykonos
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Yolo Yachting - Santorini to Mykonos

By Sail in Greece
preferred
4.7/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Mykonos, Santorini

Highlights

  • World famous clubs and wild parties (Mykonos)
  • Memorable adventures
  • Traditional vintage cruise ships
  • Experienced local tour leader

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-36%$529
8 days From$339
Price updated 1 year+ ago

Health Safety

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YOLO CRUISE - Santorini to Mykonos
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YOLO CRUISE - Santorini to Mykonos

By Sail in Greece
preferred
3.8/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Delos

Highlights

  • World famous clubs and wild parties (Mykonos)
  • Memorable adventures
  • Traditional vintage cruise ships
  • Experienced local tour leader

Themes

18 - 30's, Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-34%$516
8 days From$339
Price updated 1 year+ ago

Health Safety

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Sailing the Greek Isles
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Sailing the Greek Isles

By AdventureSmith
none
4.9/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Athens

Highlights

  • Discovering the magnificent ruins of the ancient sanctuary of Delos
  • Birthplace of Apollo and Artemis
  • Explore the picturesque village of Pyrgos
  • Immerse yourself in the lively culture, mythology, and Venetian legacy of age-old villages
  • Explore the dazzling white monastery of Panagia Hozoviotissa
Show more

Themes

Cultural, Family Friendly, National Parks, Nature & Wildlife, Small Ship Cruise, Sailing

What travelers are saying

"We particularly wanted to do this trip because of the abundance of wildlife we expected to encounter and selected this ship because they offered the kayaking experience. Overall, the weather was very good. Most people seemed like minded and were there for the adventurous experience. Accommodations Review They upgraded our cabin and we were very pleased with the amount of space and the amenities in the room. We appreciated the twin windows and being able to see humpbacks diving from our cabin. It was kept very clean and it was a treat to have our bed turned down with chocolates on the pillow each night. Meals Review We liked the variety and the quality of the food. There was always something new to try. The dining room staff was very professional and personable. Crew & Guides Review Solon was our Principal Trip Leader. He was incredibly professional and it seemed like he was constantly working to maximize the encounters with wildlife and scenery, taking advantage of all the weather opportunities and going to places that they don't often go. He worked very closely with the captain who was very accommodating and caring about us having a memorable voyage. Aymie and Andrew were our kayak guides. We went out to kayak 10 different times and were able to get to know both of them well. They worked hard to keep us safe and well informed. They made sure that we didn't miss out on any land excursions. We've had quite a few kayak guides over the years that we've paddled and we loved these two. Marla was the marine biologist aboard the ship. She was very enthusiastic and had a passion for marine mammals that was infectious. We loved listening to her presentations and looked forward to hearing her voice on the PA saying that there was another whale sighting. Colin, the geologist aboard the ship, was very knowledgeable and able to make difficult subjects understandable to the passengers. Itinerary Review The trip far, far, far, far, far, far exceeded our expectations. I had one "far" in the sentence when we left South Georgia Island after seeing 250,000 King Penguins at St. Andrews Point and added the second when we saw blue whales on two different days. The third "far" was added when we saw hundreds of whales for 6 hours along the iceberg, A68a. I added another "far" when we kayaked for over an hour with humpbacks all around and another "far" when minke whales were all around the kayaks the next day. The last "far" was added the day we didn't paddle since a leopard seal was all around the kayaks and then an orca came close. We had so many incredible experiences that we could never experience all of them in the same trip again. The guides told us that the close encounters that we had didn't happen very often and that we were very lucky that they all happened on our trip. The only thing that we didn't like was portions of the Drake Passage when it was a tad rough, but that experience gives us something to talk about. Transportation Review We made our transportation arrangements through another travel agency. Traveler Advice Make sure that you take sea sickness meds. Take advantage of every opportunity to see wildlife."

Trip dates & details
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9 days From$9,230
Price updated 1 year+ ago
More
Greek Islands Bike & Boat
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Greek Islands Bike & Boat

By UTracks
preferred
4.8/5 Excellent
62 reviews
Small Ship Cruise
Lodging level
Basic - 2 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Aegina, Athens, Mykonos, Piraeus, Poros

Highlights

  • Cycling in the Cyclade and Saronic islands with dramatic scenery
  • Exploring the small towns and villages en route
  • Swimming and snorkeling in the azure waters of Kea and Poros islands
  • Soaking up the hospitality onboard the comfortable gulet

Themes

Cycling & Biking, Small Ship Cruise, Sailing

What travelers are saying

"A really difficult company to communicate with, slow to respond and not able to accept accountability for poor service. Used Tee Travel in Spain which was even worse. Not able to organize support or assistance and harassed me about luggage that wasn't mine. There were other walkers who appeared to have more support and assistance from their travel providers. Definitely avoid this company as overpriced and no actual service."

Trip dates & details
Save this trip to your favorites or other list
8 days From$3,990
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Yolo Yachting - Mykonos to Santorini
Save this trip to your favorites or other list

Yolo Yachting - Mykonos to Santorini

By Sail in Greece
preferred
3.9/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-36%$529
8 days From$339

Health Safety

More
Sailing & Hiking in the Cyclades 8 days
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Sailing & Hiking in the Cyclades 8 days

By Personality Journeys
none
5/5 Excellent
5 reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Strenuous
Trip pace
Balanced schedule

Visits

Athens

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

Themes

Hiking & Walking, Sailing

What travelers are saying

"Dimitris was everything we could have looked for in a travel agent. Following the parameters we laid out for him, he provided us with the absolute best options for our travels. He was both honest and patient with us, and made sure we took as much time as we needed to finalize a trip that felt right for our group. Dimitris informed us on everything that was going on throughout our booking and travel process, so there were no surprises along the way. He answered every question we had and made sure we were prepared when we arrived in Athens. Andreas went above and beyond in his role as our skipper for the week. He was patient and thoughtful with our group, and put so much effort into making sure we had the best trip possible. We felt very safe and protected throughout all of our travels, and were taken to some of the most incredible place – places that weren’t even on our initial itinerary. Andreas’ expertise in his craft and his companionate demeanor are the reasons our trip was as fantastic as it was. He exceeded all of our expectations and genuinely made this trip one of the best of our lives. Thank you, Dimitris and Andreas, for giving us a week we will never forget! We can honestly say we would not have had the same experience if it wasn't for all of your help and consideration."

Trip dates & details
Save this trip to your favorites or other list
-17%$1,344
8 days From$1,112

Health Safety

More
YOLO CRUISE - Mykonos to Santorini
Save this trip to your favorites or other list

YOLO CRUISE - Mykonos to Santorini

By Sail in Greece
preferred
3.2/5 Average
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing.
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

18 - 30's, 50 plus, Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-42%$516
8 days From$299

Health Safety

More
Harmony Cruises
Save this trip to your favorites or other list

Harmony Cruises

By Sail in Greece
preferred
4.6/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Visits

Acropolis, Temple of Zeus, Venetian Lagoon

Highlights

  • Explore old cities of Athens over 3,400 years of history
  • Enjoy general city navigation and history, to philosophy, architecture
  • Enjoy all the meze and traditional Greek music to match your classic toga outfit.
  • Explore ancient town of Ermioni

Themes

Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-26%$494
8 days From$366

Health Safety

More
Yolo Yachting - Santorini to Mykonos
Save this trip to your favorites or other list

Yolo Yachting - Santorini to Mykonos

By Sail in Greece
preferred
4.7/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Mykonos, Santorini

Highlights

  • World famous clubs and wild parties (Mykonos)
  • Memorable adventures
  • Traditional vintage cruise ships
  • Experienced local tour leader

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

Trip dates & details
Save this trip to your favorites or other list
-36%$529
8 days From$339

Health Safety

More

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Greek Islands Sailing Reviews

A

AWFUL COMPANY AVOID

Nov 2019

Written on

Worst holiday experience ever - unsafe and fraudulent company

AVOID this AWFUL company

Tour:  Yolo Yachting - Mykonos to Santorini

T

Tiffany

Jun 2019

Written on

DO NOT BOOK WITH SAIL IN GREECE.

"Itinerary" and "inclusions" are completely irrelevant. We were promised a DJ, unlimited cocktails, free shots of ouzo, beach parties, boat parties. They did not del...

Tour:  Yolo Yachting - Mykonos to Santorini

B

Bhoondi

Jan 2017

Written on

The islands visited are a must! Souvlaki was our fav meal of the day!

We and me crew of 5 joined Sail in Greece yolo cruise end of September. We were on Aiolos and our skipper Christos was funny as hell! Even if when we faced a small p...

Tour:  Yolo Yachting - Mykonos to Santorini

E

Eva

Oct 2016

Written on

Quality week!

Quality week with great people on Christo's boat! Perfect mix of chilling out, ex...

Tour:  Yolo Yachting - Mykonos to Santorini

H

Helen

Oct 2016

Written on

Most valuable and Definitely 5 stars.

Definitely 5 stars.The feeling of freedom when you feel the wind on your skin during a sail, sleeping on a deck under the open sky with myriad of bright stars, every...

Tour:  Yolo Yachting - Mykonos to Santorini

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