Greece Sailing Trips & Tours

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Greece Travel Insights

Sailing the Cyclades
Map of Sailing the Greek Cyclades Islands - 8 Days
Sailing the Greek Cyclades Islands - 8 Days

Sailing the Greek islands for a week sounds amazing for good reason. Board a catamaran with an experienced crew to hop from island to stunning island in the Cyclades. Along the way, explore the best of Mykonos and watch the sunset from Santorini, see ancient ruins, and swim in the azure Aegean waters before bedding down in your boat each night.

A secluded cove in the Ionian sea, accessible only by boat
Map of Sail the Ionian Sea from Corfu - 8 Days
Sail the Ionian Sea from Corfu - 8 Days

If you love sunny days, turquoise waters, and relaxing beaches, this tour's for you! Sweep from coastal town to coastal town as you travel by yacht from Corfu to Syvota, Paxos, and more. Explore ancient ruins, sun yourself on Ionian beaches, and fall in love with everything Greece has to offer.

Mykonos harbor
Map of Luxury Cyclades Yacht Cruise - 9 Days
Luxury Cyclades Yacht Cruise - 9 Days

Cruise like a celebrity through the glittering waters of the Cyclades on this nine-day itinerary.  The Cyclades are some of the most quintessential Greek islands, and you'll see seven of them from the decks of your yacht, along with plenty of time to explore onshore. From lesser-known spots like beach-lined Milos and petite Antiparos to favorites like bustling Naxos and cosmopolitan Mykonos, you'll scope out this island chain in style.

The Cyclades Islands of Greece
Sailing the Greek Cyclades: Paros, Mykonos, Serifos - 8 Days

As the ultimate sailing adventure through Greece's coveted Cyclades Islands, this tour combines bustling city life with tranquil villages nestled in the Aegean Sea. From some of Europe's best nightlife to humble fishing towns and secluded beaches, travelers will enjoy Greece's rich and varied heritage. Enjoy sunsets and local seafood while discovering important and ancient archeological sites, all from the comfort of a private yacht.

Mykonos, Greece
Sailing the Greek Cyclades: Athens, Mykonos, Paros - 10 Days

Best for those interested in seeing Greece by boat, this sailing adventure combines bustling and ancient Athens with some of the country's most beautiful islands: the Cyclades. Set on a yacht, you'll sail the turquoise waters of the Aegean Sea in search of the region's rich heritage, including gorgeous beaches, iconic windmills, exotic plant life, and beautiful sunsets. The days are yours to indulge in rich, local cuisine, as well as discover archaeological sites, step back in time while meandering small villages, and enjoy some of the best nightlife in Greece.

Beach off of Milos
Map of Sailing Holiday in the Aegean - 9 Days
Sailing Holiday in the Aegean - 9 Days

Channel the spirit of some of Greece's most famous tales as you sail through the Aegean on this nine-day itinerary. Start off by paying the proper tribute at the Temple of Poseidon before you start on your way to Kea, followed by the villages of Kythnos. Visit the capital of the Cyclades on Syros and the home of the Cyclops on Serifos, then search for the Venus de Milo's cousin on Milos before you end your trip on the double beach of Kolona.

How it works
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Meet our Local Travel Specialists

Experienced travel agents with a passion for Greece
Travel specialist Chris Gravas
active 1 min ago

Chris Gravas

I design entire journeys that mitigate issues before they arise. I ensure the best possible orchestration of all services included. I provide human accountability in real time. My name is...

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Travel specialist Eirini Tzoka
active 1 hour ago

Eirini Tzoka

My name is Eirini, I am a travel specialist and I was born and raised in Athens. My family originated from Northwestern Greece, and it was this area's raw beauty and long-standing heritage that got...

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Travel specialist Marianna Pianelli-Blatsouka
active 25 mins ago

Marianna Pianelli-Blatsouka

I’m Marianna, born between two cultures and now based in Athens. With Greek roots and an Italian sensibility, I design tailor-made journeys throughout Greece that blend refined comfort with...

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Travel specialist Penny Vasileiadi
active 2 hours ago

Penny Vasileiadi

I’m Penny, a Travel Specialist from Kalamata. I grew up among olive groves in the Peloponnese, and that close connection to local life still shapes the way I plan trips today. With a degree in...

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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

We had a fabulous trip to Greece. I had dream...
Greece | May 9 - May 18, 2026

J
Joanie S.
Atlanta, GA | Reviewed on May 21, 2026
We had a fabulous trip to Greece. I had dreamed of traveling there since I learned about Greek History in 6th grade. I had high expectations and I was not at all disappointed. First of all, our transport drivers were on time throughout the trip, and they were professional and personable. Our hotels were all comfortable and in locations where we could walk to restaurants, etc. We were especially impressed with ALL of the staff at the Melidron in Naxos. From the front desk to the young bar... Read more

We had a fabulous trip to Greece. I had dreamed of traveling there since I learned about Greek History in 6th grade. I had high expectations and I was not at all disappointed. First of all, our transport drivers were on time throughout the trip, and they were professional and personable. Our hotels were all comfortable and in locations where we could walk to restaurants, etc. We were especially impressed with ALL of the staff at the Melidron in Naxos. From the front desk to the young bar tender, to the women who prepared the homemade breakfast to the drivers, they were always there to help with suggestions and advice, they seemed as sad to see us leave as we were to say goodbye to them. We initially wondered if it would have been a better choice to stay in/near Naxos Town, since we ended up there at some point during each day, and didn't spend time on the beach except to walk by for pretty views a couple of times. But later we decided it was nice to stay in a more peaceful area that we got to know a bit better. The Santorini hotel view was spectacular, Wow!

We enjoyed all of our tours. A few of our guides were so impressive: Evita(I think that was her name) who led us through the Acropolis was outstanding, both with her knowledge of history and adapting our walking route for those who were having a bit of trouble with physically walking for long periods. Elizabeth in Naxos was fantastic, and George in Santorini was a very good guide as well. Our driver to Delphi, Nancy, was not a licensed guide, but we learned so much from her on the trip. She had lots of knowledge about Greece to share with us. We wanted to do a day trip outside of Athens and followed Siena's advice to go to Delphi. I don't think any of us knew anything about that place so I can't say we were excited, but it turns out we all really enjoyed learning about the history. Our guide there, Theo, was very knowledgeable and shared so much information about that city. I will mention that later we all commented that he was not so easy to understand, we all felt like we had to focus very intently to understand what he was saying. He seemed to talk very quickly and did not annunciate as clearly as our other guides. But we all really loved that day, including driving through two really cute towns up there, and the restaurant for lunch. I would love to go back there one day and explore the towns. We were a bit skeptical about how the marble carving experience in Naxos would be, it turns out that we all enjoyed a very different activity very much. We were also worried we would be very cold on the catamaran trip, after the weather report showed cool temps with lots of wind, but overall, it was sunny and quite comfortable until the sun went down.

The whole kimkim team was incredible. Siena listened to our needs and planned and a wonderful trip, willing to change things as needed. There were a few times we had questions while we were away, when we knew it was the middle of the night in the US. Each time somebody got back to us within minutes. It was truly amazing how quickly we would get a reply, even in the middle of the night on a weekend. We truly cannot hesitate to recommend kimkim to anyone, they make traveling so comfortable and easy. We would be happy to come back to any of these places again but there is also so much more of Greece to see. Can't wait to plan our next trip, the next one for us will be Croatia and Montenegro, about a year from now.

Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on May 21, 2026

Joanie, I absolutely loved working with you! Thank you for sharing all the photos throughout your trip. I felt like I was there with you all! I'm so happy our team delivered on your expectations, and you loved our vetted guides, hotels, and drivers. The Melidron Hotel & staff are especially lovely, I fully agree! I hope we get to work together again, but in the meantime, enjoy all of these Greece memories! 🇬🇷🕊️✨

We were paired with Sydney as our Greece spec...
Greece | May 4 - May 14, 2026

B
Bill C.
Newark, NJ | Reviewed on May 20, 2026

We were paired with Sydney as our Greece specialist. It was the trip of a lifetime and I can’t stress how great Sydney was! EVERY place we stayed was in the perfect area. EVERY tour we went on was amazing! EVERY ride showed up right on time! We couldn’t have used a more knowledgeable and helpful planner. Perfect to a tee. Already thinking about what other country we will use KimKim for. Can’t wait!

Local specialist: Sydney Hubbard

Wonderful trip to Greece!
Greece | May 9 - May 18, 2026

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Jeff S.
Atlanta, GA | Reviewed on May 20, 2026
All I can say about our trip to Greece is that it was wonderful . . . The Kim Kim Team was amazing and truly made a difference all the way through — from itinerary development, to planning and logistics, and responding to questions and issues along the way. Regardless of time — day or night — Kim Kim responded very quickly and was always helpful. All of the logistics from the US to Athens to Naxos to Santorini were flawless!! With all of the drivers and guides and passes/tickets... Read more

All I can say about our trip to Greece is that it was wonderful . . . The Kim Kim Team was amazing and truly made a difference all the way through — from itinerary development, to planning and logistics, and responding to questions and issues along the way. Regardless of time — day or night — Kim Kim responded very quickly and was always helpful. All of the logistics from the US to Athens to Naxos to Santorini were flawless!! With all of the drivers and guides and passes/tickets involved in the trip it was amazing that everything worked exactly as planned. The Kim Kim app with the itinerary, contact names and phone, tickets etc along with the chat feature was tremendously useful. The hotels were great, the drivers were prompt and courteous, the guides were knowledgeable and very easy/flexible to work with. I can’t say enough good things — probably the best trip that we’ve ever taken and Kim Kim was a key contributor. Will definitely use them in the future.

Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on May 21, 2026

The "best trip you've ever taken" is the highest reward we could ask for, Jeff! Thank you so much for sharing your experience, and I'm especially glad you enjoyed using our new app! It was so much fun working together, and I hope you have another trip of a lifetime with kimkim in Croatia next year! 🤩

Why travelers love kimkim

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