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.

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Meet our Local Travel Specialists

Experienced travel agents with a passion for Greece
Travel specialist Marianna Loupou
active 28 mins ago

Marianna Loupou

I’m a travel specialist with a genuine love for creating one-of-a-kind experiences that feel just right for each traveler. My journey in the travel world has taken me through many exciting paths, ...

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Travel specialist Chris Gravas
active 1 hour 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 Marianna Pianelli-Blatsouka
active 2 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 Effie Parasyrakis
active 22 hours ago

Effie Parasyrakis

My name is Effrosyni, I typically originate from the island of Crete but I was born and raised in Athens, Greece. I have lived for 8 months in France and 3 years in Santorini, Greece. I have a...

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Trip Reviews for Greece

The latest reviews by travelers who booked their trip on kimkim

Best Trip of Our Lives!
Greece | Sep 4 - Sep 15, 2025

D
Dylan R.
Ashburn, VA | Reviewed on Mar 27, 2026
We had an amazing time on our trip to Greece and still think about it often to this day. Everything was planned perfectly and we had little to worry or think about besides enjoying our time. All transportation was seamless and the hotels were excellent. Sienna did an absolute amazing job based on my initial guidance and we made very small changes to her first itinerary. 6/5 stars! Only comments we have just to assist future travelers:
1. The travel from the ferry to the hotel in Sifnos is... Read more

We had an amazing time on our trip to Greece and still think about it often to this day. Everything was planned perfectly and we had little to worry or think about besides enjoying our time. All transportation was seamless and the hotels were excellent. Sienna did an absolute amazing job based on my initial guidance and we made very small changes to her first itinerary. 6/5 stars!

Only comments we have just to assist future travelers:
1. The travel from the ferry to the hotel in Sifnos is very short and probably does not require a car.
2. It is recommended to tip 10% on all tours, but with everything being booked through KimKim we had no idea what 10% was. Maybe just include a note for recommended amount on each tour/excursion?

Hotel Reviews
SanSal Boutique Hotel
Chania

Great location and friendly staff

Authenticity & Character
Location
I
Staff
Cleanliness & Comfort
NLH Monastiraki
Athens
Authenticity & Character
Location
Staff
Cleanliness & Comfort
Manili Boutique Suites & Villas
Archanes

Very Nice

Authenticity & Character
Location
Staff
We were only here for one night, but it was special nonetheless
Cleanliness & Comfort
Liana Beach Hotel & Spa
Naxos

Could have stayed here for the rest of my life and been happy!

Authenticity & Character
Location
Perfect spot on the island. Our room was a short walk to the private part of the beach. We could just relax and be served right in the chairs.
Staff
Very helpful. Coordinated a rental car to be dropped off for us right at the hotel.
Cleanliness & Comfort
Sifnos House
Sifnos

Amazing location with great staff!

Authenticity & Character
Location
Short walk from the ferry and a really great spot on the island.
Staff
Awesome! Very helpful!
Cleanliness & Comfort
Activity Reviews
Private Sailing Trip to Balos Beach & Gramvousa Island
Private Sailing Trip to Balos Beach & Gramvousa Island
Chania

Another great boat day and a perfect way to end the trip. We once again had the boat to ourselves and a great crew to make us feel special.

Quality of Experience
Guides, Drivers and Staff
Transport
Samaria Gorge Hiking Day Trip
Samaria Gorge Hiking Day Trip
Chania

A lot of work, but some of the most amazing views Ive ever seen! Drive back down was very windy, so if you get carsick just be prepared.

Quality of Experience
Guides, Drivers and Staff
Transport
Traditional Cretan Cooking Experience
Traditional Cretan Cooking Experience
Chania

Made to felt like part of the family and had some truly amazing food made by us!

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Private Culture Walk with Food Tastings & Tavern Meal
Private Culture Walk with Food Tastings & Tavern Meal
Naxos

Best food of the trip! The culture we saw was amazing as well. Each island truly has its own history.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Half Day Private Boat Outing to South Naxos
Half Day Private Boat Outing to South Naxos
Naxos

So great! We had the boat to ourselves and the captain truly made us feel special. Much better than the crowded catamarans we saw around. We were able to go place to place much faster.

Quality of Experience
Guides, Drivers and Staff
Transport
Private Hike in South Sifnos
Private Hike in South Sifnos
Sifnos

Very nice. Would like to have had a little more time to hangout, but amazing nontheless.

Quality of Experience
Guides, Drivers and Staff
Transport
Taste of Sifnos: Food, Culture & Village Life
Taste of Sifnos: Food, Culture & Village Life
Sifnos

Delicious! Felt like a local!

Quality of Experience
Guides, Drivers and Staff
Transport
Self-Guided Lycabettus Hill Visit
Self-Guided Lycabettus Hill Visit
Athens
Ancient Athens Acropolis & Mythology Walk
Ancient Athens Acropolis & Mythology Walk
Athens

Very fun and interesting.

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Siena Mueller
Siena
Siena Mueller
Local specialist in Kimkim HQ | Replied on Mar 30, 2026

Thank you so much for taking the time to share this amazing feedback! Making sure your honeymoon was a 6-star experience was my ultimate goal. It sounds like your hotels & experiences were incredible. I hope you'll travel with kimkim again in the future (maybe a 1-year anniversary trip?)! ❤️✨

Read all Greece reviews

The guides were all very knowledgeable and fr...
Greece | Mar 2 - Mar 9, 2026

Lee
Lee G.
Chicago, IL | Reviewed on Mar 11, 2026
The guides were all very knowledgeable and friendly. Yiannis was excellent and was a fine companion. He made everything so easy for me. There was so much to see in a short time and the schedule made it possible to see all of the sights I wished for. The accommodations were excellent. I hope to come back some day and see more of your beautiful country! Read more

The guides were all very knowledgeable and friendly. Yiannis was excellent and was a fine companion. He made everything so easy for me. There was so much to see in a short time and the schedule made it possible to see all of the sights I wished for. The accommodations were excellent. I hope to come back some day and see more of your beautiful country!

Hotel Reviews
Monastiri Guesthouse
Kalampaka - Meteora
DAYS City Suites
Patras
Leto Nuevo Hotel
Nafplio
Mosaikon
Athina
Activity Reviews
Ancient Corinth Guided Tour
Ancient Corinth Guided Tour
Greece
Acropolis Guided Tour
Acropolis Guided Tour
Athens
Local specialist: Marianna Loupou
Read all Greece reviews

We had such an incredible time on our trip to...
Greece | Oct 6 - Oct 14, 2025

J
Joanna W.
Chicago, IL | Reviewed on Feb 17, 2026
We had such an incredible time on our trip to Greece! Angela (Aggeliki) was incredible to work with. We were nervous having never used KimKim before, but it turned out to be a great decision for us. Angela helped us create a great itinerary, was always available and responsive if we had questions or changes during the trip, and ensured everything was easy and streamlined. All our transportation drop-offs and pickups were on time and easy to navigate. She sent us all our ferry tickets in... Read more

We had such an incredible time on our trip to Greece! Angela (Aggeliki) was incredible to work with. We were nervous having never used KimKim before, but it turned out to be a great decision for us. Angela helped us create a great itinerary, was always available and responsive if we had questions or changes during the trip, and ensured everything was easy and streamlined. All our transportation drop-offs and pickups were on time and easy to navigate. She sent us all our ferry tickets in advance. All the tours were incredible - especially the individual tour in Tinos and the small group tour in Santorini. We loved the hotels she picked for their unique features and charms. Overall we had a blast!!

Hotel Reviews
14 Reasons Why
Athens

Excellent breakfast, centrally located, perfect home-base for a few days in Athens!

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Infinity View Hotel Tinos
Tinos

LOVED this hotel. Views were incredible. Make sure to use the bug deterrent thing on the wall, though, if you're going to keep your windows open!

Authenticity & Character
Location
Staff
Cleanliness & Comfort
Activity Reviews
Athens Highlights Mythology Tour
Athens Highlights Mythology Tour
Greece

Great tour, considering how crowded this area of Athens is! Very informative, great guide, good equipment so we could hear.

Naxos Town Food Tour - afternoon with dinner
Naxos Town Food Tour - afternoon with dinner
Naxos

I thought this was a good tour. However, such a large group was a bit trickier to navigate. And Naxos is so small that we ended up visiting several places that I had already visited in my first day of sightseeing the area.

Quality of Experience
Guides, Drivers and Staff
Athens Wine Tasting Tour & Nightlife
Athens Wine Tasting Tour & Nightlife
Athens

Fotis was a lovely guide, we learned a lot about local food and liquors - such a fun start to our Athens visit!

Quality of Experience
Guides, Drivers and Staff
Panoramic Tour 2025
Panoramic Tour 2025
Santorini

Great tour - Maria was a lovely guide! I was a little bummed that our itinerary had initially included Oja but then the tour didn't go there - but regardless, we still had a fantastic time on this tour! Highly recommend.

Quality of Experience
Guides, Drivers and Staff
Transport
Tinos Full Day Tour
Tinos Full Day Tour
Tinos

Tour guide was wonderful - love how the tour was so individualized and took us to lots of unique locations all across Tinos. One of my favorite parts of our Greece trip.

Quality of Experience
Guides, Drivers and Staff
Transport
Local specialist: Angela (Aggeliki) Giannioti
Angela (Aggeliki)
Angela (Aggeliki) Giannioti
Local specialist in Greece | Replied on Feb 17, 2026

Yeia sou Joanna,

Thank you so much for sharing your feedback on your experience.
I am delighted to know that you had a wonderful time here in Greece with us.
Tinos is one of my favorite, too! Has this charm and such a relaxing vibe, right?
We would love to see you coming back one day. There are so many more I would be thrilled to show you in my amazing country. 🙂

Until our paths meet again take care and safe travels!
Angela and the GA Trips team

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