Greek Islands Small Ship Cruise Trips & Packages Tours & Trips

12 Greek Islands Small Ship Cruise Trips & Packages trips. Tours from 6 tour companies. 63 reviews.

12 Trips match your criteria (1 - 12 shown)

Sailing the Greek Isles
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Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

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

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."

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Yolo Yachting - Santorini to Mykonos
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Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

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

Themes

Sailing, Small Ship Cruise, Singles Travel

What travelers are saying

"I am writing on behalf of 20 passengers who sailed aboard the vessel EROS, under the co,mmand of Captain Georgios Paraskevas, during our trip in Greece from August 10-17, which commenced in Corfu. Unfortunately, our experience was marred by several significant technical difficulties that severely impacted our journey. Firstly, we encountered a malfunction with the anchor system, along with an issue beneath the vessel that led to an entire day being lost while waiting for a spare part to be replaced. Additionally, there was a persistent and strong smell of gasoline in the rooms throughout the trip, which we found to be extremely dangerous and unsettling. This issue greatly affected the comfort and safety of the passengers. The cooling system also failed to function, forcing many passengers to sleep on the deck in discomfort. Furthermore, it became apparent that the captain lacked the necessary skills to operate the vessel effectively, as it was primarily managed by the Egyptian crew, who appeared to be guiding the captain in performing essential tasks. This was both obvious and quite alarming to all on board. In summary, we are relieved that the trip concluded without any serious incidents, but we remain concerned about the overall safety and operation of the vessel. Therefore, I would like to inquire if the EROS is fully licensed and regularly inspected in accordance with Greek and EU standards prior to being leased out. Please provide a detailed response regarding this matterAdditionally, several other issues arose during the trip that were not mentioned in our initial email. These include: Persistent and significant flooding of the bathroom floors and leakage of the sewage water making the bathroom usage difficult, exposing us to potential waterborne diseases and extremely unpleasant smell in the cabins and throughout the hallway. A near collision with another sailing boat Collisions with boat during passenger transfers to the beach ( AntiPaxos) An incident at Lefkada beach, where a lifeguard called the police to protest our boat’s disembarkation (Lefkada) Frequent turn offs of the air conditioning along with gas infused fumes and extremely unpleasant sewage smells were forcing passengers to sleep on the deck outside. Even the ships that were docked alongside our ship were complaining about our exhaust fumes (Nidri)."

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Yolo Yachting - Mykonos to Santorini
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Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

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

Sailing, Small Ship Cruise, Singles Travel

What travelers are saying

"I am writing on behalf of 20 passengers who sailed aboard the vessel EROS, under the co,mmand of Captain Georgios Paraskevas, during our trip in Greece from August 10-17, which commenced in Corfu. Unfortunately, our experience was marred by several significant technical difficulties that severely impacted our journey. Firstly, we encountered a malfunction with the anchor system, along with an issue beneath the vessel that led to an entire day being lost while waiting for a spare part to be replaced. Additionally, there was a persistent and strong smell of gasoline in the rooms throughout the trip, which we found to be extremely dangerous and unsettling. This issue greatly affected the comfort and safety of the passengers. The cooling system also failed to function, forcing many passengers to sleep on the deck in discomfort. Furthermore, it became apparent that the captain lacked the necessary skills to operate the vessel effectively, as it was primarily managed by the Egyptian crew, who appeared to be guiding the captain in performing essential tasks. This was both obvious and quite alarming to all on board. In summary, we are relieved that the trip concluded without any serious incidents, but we remain concerned about the overall safety and operation of the vessel. Therefore, I would like to inquire if the EROS is fully licensed and regularly inspected in accordance with Greek and EU standards prior to being leased out. Please provide a detailed response regarding this matterAdditionally, several other issues arose during the trip that were not mentioned in our initial email. These include: Persistent and significant flooding of the bathroom floors and leakage of the sewage water making the bathroom usage difficult, exposing us to potential waterborne diseases and extremely unpleasant smell in the cabins and throughout the hallway. A near collision with another sailing boat Collisions with boat during passenger transfers to the beach ( AntiPaxos) An incident at Lefkada beach, where a lifeguard called the police to protest our boat’s disembarkation (Lefkada) Frequent turn offs of the air conditioning along with gas infused fumes and extremely unpleasant sewage smells were forcing passengers to sleep on the deck outside. Even the ships that were docked alongside our ship were complaining about our exhaust fumes (Nidri)."

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Custom Designed Trip
Lodging level
lodgingLevelName
Physical level
N/A

Highlights

  • Fully customized trip based on preferences
  • Matched with a local specialist
  • From $150 per person per day
Self-Guided / Independent Tour
YOLO CRUISE - Mykonos to Santorini
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Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

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

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

What travelers are saying

"I am writing on behalf of 20 passengers who sailed aboard the vessel EROS, under the co,mmand of Captain Georgios Paraskevas, during our trip in Greece from August 10-17, which commenced in Corfu. Unfortunately, our experience was marred by several significant technical difficulties that severely impacted our journey. Firstly, we encountered a malfunction with the anchor system, along with an issue beneath the vessel that led to an entire day being lost while waiting for a spare part to be replaced. Additionally, there was a persistent and strong smell of gasoline in the rooms throughout the trip, which we found to be extremely dangerous and unsettling. This issue greatly affected the comfort and safety of the passengers. The cooling system also failed to function, forcing many passengers to sleep on the deck in discomfort. Furthermore, it became apparent that the captain lacked the necessary skills to operate the vessel effectively, as it was primarily managed by the Egyptian crew, who appeared to be guiding the captain in performing essential tasks. This was both obvious and quite alarming to all on board. In summary, we are relieved that the trip concluded without any serious incidents, but we remain concerned about the overall safety and operation of the vessel. Therefore, I would like to inquire if the EROS is fully licensed and regularly inspected in accordance with Greek and EU standards prior to being leased out. Please provide a detailed response regarding this matterAdditionally, several other issues arose during the trip that were not mentioned in our initial email. These include: Persistent and significant flooding of the bathroom floors and leakage of the sewage water making the bathroom usage difficult, exposing us to potential waterborne diseases and extremely unpleasant smell in the cabins and throughout the hallway. A near collision with another sailing boat Collisions with boat during passenger transfers to the beach ( AntiPaxos) An incident at Lefkada beach, where a lifeguard called the police to protest our boat’s disembarkation (Lefkada) Frequent turn offs of the air conditioning along with gas infused fumes and extremely unpleasant sewage smells were forcing passengers to sleep on the deck outside. Even the ships that were docked alongside our ship were complaining about our exhaust fumes (Nidri)."

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YOLO CRUISE - Santorini to Mykonos
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Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

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

Themes

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

What travelers are saying

"I am writing on behalf of 20 passengers who sailed aboard the vessel EROS, under the co,mmand of Captain Georgios Paraskevas, during our trip in Greece from August 10-17, which commenced in Corfu. Unfortunately, our experience was marred by several significant technical difficulties that severely impacted our journey. Firstly, we encountered a malfunction with the anchor system, along with an issue beneath the vessel that led to an entire day being lost while waiting for a spare part to be replaced. Additionally, there was a persistent and strong smell of gasoline in the rooms throughout the trip, which we found to be extremely dangerous and unsettling. This issue greatly affected the comfort and safety of the passengers. The cooling system also failed to function, forcing many passengers to sleep on the deck in discomfort. Furthermore, it became apparent that the captain lacked the necessary skills to operate the vessel effectively, as it was primarily managed by the Egyptian crew, who appeared to be guiding the captain in performing essential tasks. This was both obvious and quite alarming to all on board. In summary, we are relieved that the trip concluded without any serious incidents, but we remain concerned about the overall safety and operation of the vessel. Therefore, I would like to inquire if the EROS is fully licensed and regularly inspected in accordance with Greek and EU standards prior to being leased out. Please provide a detailed response regarding this matterAdditionally, several other issues arose during the trip that were not mentioned in our initial email. These include: Persistent and significant flooding of the bathroom floors and leakage of the sewage water making the bathroom usage difficult, exposing us to potential waterborne diseases and extremely unpleasant smell in the cabins and throughout the hallway. A near collision with another sailing boat Collisions with boat during passenger transfers to the beach ( AntiPaxos) An incident at Lefkada beach, where a lifeguard called the police to protest our boat’s disembarkation (Lefkada) Frequent turn offs of the air conditioning along with gas infused fumes and extremely unpleasant sewage smells were forcing passengers to sleep on the deck outside. Even the ships that were docked alongside our ship were complaining about our exhaust fumes (Nidri)."

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Harmony Cruises
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Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

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

Sailing, Small Ship Cruise

What travelers are saying

"I am writing on behalf of 20 passengers who sailed aboard the vessel EROS, under the co,mmand of Captain Georgios Paraskevas, during our trip in Greece from August 10-17, which commenced in Corfu. Unfortunately, our experience was marred by several significant technical difficulties that severely impacted our journey. Firstly, we encountered a malfunction with the anchor system, along with an issue beneath the vessel that led to an entire day being lost while waiting for a spare part to be replaced. Additionally, there was a persistent and strong smell of gasoline in the rooms throughout the trip, which we found to be extremely dangerous and unsettling. This issue greatly affected the comfort and safety of the passengers. The cooling system also failed to function, forcing many passengers to sleep on the deck in discomfort. Furthermore, it became apparent that the captain lacked the necessary skills to operate the vessel effectively, as it was primarily managed by the Egyptian crew, who appeared to be guiding the captain in performing essential tasks. This was both obvious and quite alarming to all on board. In summary, we are relieved that the trip concluded without any serious incidents, but we remain concerned about the overall safety and operation of the vessel. Therefore, I would like to inquire if the EROS is fully licensed and regularly inspected in accordance with Greek and EU standards prior to being leased out. Please provide a detailed response regarding this matterAdditionally, several other issues arose during the trip that were not mentioned in our initial email. These include: Persistent and significant flooding of the bathroom floors and leakage of the sewage water making the bathroom usage difficult, exposing us to potential waterborne diseases and extremely unpleasant smell in the cabins and throughout the hallway. A near collision with another sailing boat Collisions with boat during passenger transfers to the beach ( AntiPaxos) An incident at Lefkada beach, where a lifeguard called the police to protest our boat’s disembarkation (Lefkada) Frequent turn offs of the air conditioning along with gas infused fumes and extremely unpleasant sewage smells were forcing passengers to sleep on the deck outside. Even the ships that were docked alongside our ship were complaining about our exhaust fumes (Nidri)."

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Greek Islands Bike & Boat
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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, Sailing, Small Ship Cruise

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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Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

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
Show more

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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Greek Islands Small Ship Cruise Trips & Packages Reviews

B

Bruce

Nov 2016

Written on

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

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

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

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

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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