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Greece Small Ship Cruise Tours & Trip Packages

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Island Hopping: Athens, Mykonos, Naxos, Santorini

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

Private Guided

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Highlights

Marvel the impressive Acropolis and the New Acropolis museum
Discover the iconic Mykonos town
Taste and learn about the traditional products of Naxos
Learn all about the unique wines of Santorini
Visit Akrotiri prehistoric town of Santorini

Themes

Cultural, Nature & Wildlife, Family Friendly, Education / Learning, Photography, High Adventure, Small Ship Cruise

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

Trip dates & details

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$5,034

9 days From$3,729

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Island Hopping: Tinos, Naxos, and Santorini

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

Small Group Tour

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Highlights

Marvel the impressive Acropolis
Have an introduction to Greek flavors and cuisine
Learn the secrets of marble sculpting in Tinos
Explore Naxos, the biggest island of the Cyclades
Witness the unique sunset cruise around the volcano

Themes

Cultural, Culinary & Wine, High Adventure, Small Ship Cruise

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

Trip dates & details

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13 days

Inquire

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Sail Greece: Santorini to Mykonos

By Intrepid Travel

premier

Small Ship Cruise

Why we love them

They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Akrotiri, Mykonos, Santorini

Highlights

Spend your days island-hopping in the Cyclades, swimming in the clear waters of the Aegean and sleeping aboard a yacht.
See Santorini, where the blue and white villages cling to the rim of an ancient volcano – don't worry, the only fire you’ll see is in the island’s magnificent sunsets.
Break bread with locals in the sleepy fishing villages of the Small Cyclades islands, away from the typical tourist trail.
Taste rural life on the large island of Naxos – a mix of historic neighbourhoods and Kitron liqueur.
Explore a place where Europe’s chic and beautiful come to play – you’ll have plenty of time to soak up the beauty, charm and sunsets of Mykonos.

Themes

Sailing, Small Ship Cruise

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

Trip dates & details

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$2,562

8 days From$1,898

Health Safety +

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Yolo Yachting - Mykonos to Santorini

By Sail in Greece

preferred

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)."

Trip dates & details

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8 days From$339

Health Safety

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Greece Sailing Adventure: Cyclades Islands

By Intrepid Travel

premier

Small Ship Cruise

Why we love them

They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.

Lodging level

Standard - 3 star

Physical level

Moderate

Trip pace

Flexible schedule

Visits

Mykonos, Santorini

Highlights

A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.
Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life. This is island living, Greek style.
Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.
No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

Themes

Sailing, Small Ship Cruise

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

Trip dates & details

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$3,497

10 days From$2,590

Health Safety +

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Athens, Crete, Milos and Santorini Travel Package

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

Private Guided

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Full schedule

Highlights

Marvel the impressive Acropolis
Explore Athens in a tasty way with your food guide
Hike through the biggest gorge in Europe
Leisure Stroll with tastings in the picturesque town along the Santorini cliff
Unique sunset cruise around the volcano in Santorini

Themes

Cultural, Culinary & Wine, Hiking & Walking, Photography, Small Ship Cruise

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

Trip dates & details

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$4,243

13 days From$3,143

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YOLO CRUISE - Mykonos to Santorini

By Sail in Greece

preferred

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)."

Trip dates & details

Save this trip to your favorites or other list

8 days From$299

Health Safety

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A Romantic 10 day trip to Greece. Athens, Paros, Mykonos, Santorini

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

Private Guided

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Highlights

Embark of a day sailing cruise in Mykonos
Taste what the volcanic soil of Santorini has to offer
Learn about the Acropolis of Athens and its emblematic Parthenon
Explore the island of Paros at your own pace

Themes

Cultural, Culinary & Wine, Hiking & Walking, Sailing, Photography, Small Ship Cruise

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

Trip dates & details

Save this trip to your favorites or other list

$5,345

10 days From$3,959

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Greece Small Ship Cruise Tours & Trips

35 Greece Small Ship Cruise trips. Tours from 23 tour companies. 90 reviews.

Island Hopping: Athens, Mykonos, Naxos, Santorini

Island Hopping: Tinos, Naxos, and Santorini

Sail Greece: Santorini to Mykonos

Yolo Yachting - Mykonos to Santorini

Greece Sailing Adventure: Cyclades Islands

Athens, Crete, Milos and Santorini Travel Package

YOLO CRUISE - Mykonos to Santorini

A Romantic 10 day trip to Greece. Athens, Paros, Mykonos, Santorini

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Greece Small Ship Cruise Reviews

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