Greek Islands Small Ship Cruise Tours & Trip Packages

Greek Islands Small Ship Cruise Tours & Trips

7 Greek Islands Small Ship Cruise trips. Tours from 4 tour companies. 51 reviews.

7 Trips match your criteria (1 - 7 shown)

Yolo Yachting - Mykonos to Santorini
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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"

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YOLO CRUISE - Mykonos to Santorini
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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
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Harmony Cruises
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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
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YOLO CRUISE - Santorini to Mykonos
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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
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Sailing the Greek Isles
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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
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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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Greek Islands Bike & Boat
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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."

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Greek Isles & Turkish Delights
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3/5 Average
32 reviews
Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Acropolis, Athens, Blue Mosque, Istanbul, Mykonos, Santorini

Highlights

  • The Parthenon and the Acropolis in Athens
  • Palace of the Grand Masters in Rhodes
  • White-washed buildings and blue domes of Santorini
  • Blue Mosque and Grand Bazaar in Istanbul
  • Chic boutiques and cafés of Mykonos
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Themes

Cultural, Small Ship Cruise

What travelers are saying

""I do not recommend Windstar Cruises, at least not onboard 'Windstar'. The only reason I could see to sail with them is for the evening event in Ephesus, which was unforgettable. Reaching them via telephone, pre-cruise took 45mins+. Questions regarding one of Windstar's Private Driver & Guide tours I inquired about were not responded to, nor was a phone call made to me to report back. Instead, after 11pm, on the 3rd night onboard, I received an unacceptable, vague reply. Fortunately, in the week prior to cruise, my travel agent did a wonderful job of contacting a local tour/guide operator, and I had a wonderful experience. I sailed on The Windstar in August 2022 for a Greek Isles cruise. Unfortunately, I was underwhelmed in most aspects, except for the spa staff, who were wonderful, and cabin stewards, dining staff, and pool area bartenders/staff, who were excellent. While realizing it is a smaller 'sailing' ship, it needs a major upgrade/overhaul, or perhaps replacement with a new ship. Public areas, were substandard, pool had unsightly rusty colored sediment around the base of the waterline, whirlpool was neither heated, nor cooled, bed was uncomfortable, many times announcements by Captain could not be heard in cabin, nor were they repeated, in full, and slowly, a second time. Announcements meant for hallways or public areas only also were stated very quickly, and not repeated, slowly and with enunciation. I felt the destination briefings could have been interactive, with repeated times, and a fun, learning experience, with some ideas of what, and how, to experience the islands, other than the Windstar, or alternate booked excursions. Such as having information on car rentals, motorbike rentals, and perhaps a packet with information on all port calls, with maps, in the cabins, upon check-in, or a designated, sit-down office, wherein one could obtain information, comfortably, without interruptions. While I realize all lines are short-staffed the past couple of years, I felt it was grossly understaffed in the dissemination of information, reception, and destination briefing department, and that staff could have been available for a longer period of time for public Q & A's. I was actually distracted with number of times I heard 'Ladies & Gentlemen', during destination briefings, after almost every single sentence, that it interfered with information being given. While an understanding was reached after a couple days, and Reception improved, I was, one time, given an 'attitude' by reception staff, which won't easily be forgotten. My cabins portholes had exterior rust sediment build up which interfered with a nice view outside the portholes, and the smaller drain in the bathroom/head, outside the shower stall, had water coming up into/onto the toilet area and left the floorboards with that awful squeaky sound and also disallowed the use of fluffy area rug, instead needing 3 large towels to dry area after a shower. After this was reported to Manager, it was fixed, but by the night prior to end of cruise, it started happening again. I also feel the cruise rates, as compared to other lines, are overpriced. Perhaps Windstar's other, newer ships are different. One can only hope.""

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

Health Safety

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

Health Safety

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

Health Safety

More
YOLO CRUISE - Santorini to Mykonos
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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
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Health Safety

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Greek Islands Small Ship Cruise Reviews

A

AWFUL COMPANY AVOID

Nov 2019

Written on

Worst holiday experience ever - unsafe and fraudulent company

AVOID this AWFUL company

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...

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...

E

Eva

Oct 2016

Written on

Quality week!

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

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...

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