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Dream vacation in Greece with a Catamaran

Your Yacht Your Captain Your Chef

Explore Greece aboard your own luxury catamaran with a dedicated Captain and Chef. Since 1999, Yachtsailing.com has been crafting unforgettable sailing experiences across the Greek islands - combining comfort, privacy, and local expertise for a truly seamless journey at sea.

Our fleet

Explore our curated yacht offers

King of Diamonds, 56 ft

A Lagoon 560 S2 flagship where elegance meets a confident, unhurried rhythm - six staterooms for up to ten guests, refit in 2025. Crewed by an experienced captain and host chef, built for moments that linger long after the anchor is raised.

Staterooms 6 • Up to 10 Guests • Refit 2025

from / week
€14,000
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Ace of Diamonds, 52 ft

Bright, open decks and a flybridge made for sunset moments under sail - six cabins for up to ten guests, refit in 2025. The flybridge is where the evenings end up, drink in hand, islands going gold.

Staterooms 6 • Up to 10 Guests • Refit 2025

from / week
€9,000
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Ace of Hearts, 52 ft

Composed and inviting, with generous living spaces and an elegant flow - seven cabins that comfortably host up to twelve guests, refit in 2025. Roomy enough for a big group to spread out and still feel together.

Staterooms 6 • Up to 12 Guests • Refit 2026

from / week
€11,000
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Baccarat, 45 ft

Comfortable and effortlessly enjoyable - four cabins for up to eight guests aboard a Lagoon 450 Flybridge, refit in 2024. Generous deck space for sun-filled days and easy evenings at sea.

Staterooms 4 • Up to 8 Guests • Refit 2024

from / week
€5,000
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Baron, 52 ft

Understated luxury and easy comfort across sun-filled decks and calm anchorages - six cabins for up to ten guests, refit in 2025. A quietly confident catamaran built for slow mornings and long lunches at anchor.

Staterooms 6 • Up to 10 Guests • Refit 2026

from / week
€11,500
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Casino Royale, 50 ft

Nimble and welcoming, ideal for exploring the Cyclades at your own pace - six cabins for up to ten guests, refit in 2024. Light enough to feel quick, roomy enough to feel generous.

Staterooms 6 • Up to 10 Guests • Refit 2024

from / week
€7,600
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Fantasy, 42 ft

A relaxed, straightforward way to enjoy life at sea - four cabins for up to six guests aboard a compact Lagoon 420, refit in 2022. Easy days and stress-free cruising for smaller groups.

Staterooms 4 • Up to 4 Guests • Refit 2022

from / week
€4,000
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Poker Face, 45 ft

Relaxed, confident and easygoing - four cabins for up to eight guests aboard a Lagoon 450 Flybridge, refit in 2023. One of the fleet’s most consistently booked catamarans.

Staterooms 4 • Up to 8 Guests • Refit 2023

from / week
€5,000
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View all yachts

Your Summer in the Greek Islands

An authentic and genuine experience of the Greek lifestyle. History, culture, and flavors this beautiful country has to offer - taken in through breathtaking views, tavernas, bars, and beautiful beaches, as well as incredible landmarks and monuments which echo back into the ages.

25+ years sailing these waters Hundreds of guest reviews

See what our guests have to say

Real stories from our guests, sharing their unique journeys and unforgettable moments while exploring Greece's beauty with YachtSailing

Google reviewsTripadvisor
We were dealt a Royale Flush on the Casino Royale catamaran in the Greek islands. Yachtsailing.com made the transition from our hotel to boat a breeze by Eugene and his staff. We got greeted by our Captain Haris and our Hostess Vicky with a very warm welcome. They were very informative and accommodating from the get go. All nine of us agreed we were so happy that we chose to have a Captain and Hostess because it made it truly a vacation.
SuzyKfrom USA · chartered Casino Royale to the Cyclades
The "Casino Royal" boat was pure magic. I listened to the wisdom of Yacht Sailing guru Eugene - who helped me plan a stunning week long adventure with Vicky & Captain Harris which gave our group the time to explore and rest in perfect measures. If you want a top-notch, warm hearted experience ... book the casino royal with this amazing crew. You won't want to go home.
j4metoochartered Casino Royale to the Saronic
This is my first time on a catamaran. I didn't know what to expect so everything was a new experience for me. From the time I arrived at the Alimos Marina and was greeted by Joanna and Eugene I felt very comfortable. In a short time we sat down with our Captain, George, who explained the salient points and answered all our questions. This was a trip of a lifetime for my husband and myself.
lizziebillchartered VEGAS to the Cyclades
Just spent a magical week cruising around the Cyclades with captain George Maleas and our group of three couples. Everything far exceeded our expectations from the quality of the catamaran to the places we visited to our knowledgeable captain. We visited Poros, Milos, Kimolos, Serifos, and Kythnos and each island was more beautiful than the last.
Guest reviewchartered a catamaran to the Cyclades

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Frequently asked questions

01Is the itinerary fixed, or can we customize our route? +

All our trips are fully customizable. There is no fixed itinerary. The final route is shaped together with you, based on your preferences (how many hours you wish to sail per day, sightseeing or relaxation, hiking, swimming, local cuisine, etc.) and - most importantly - the weather at the time of your trip. The captain adjusts the plan daily to keep the experience relaxed, safe and enjoyable, and you can stay longer at places you love.

02Cyclades or Saronic Islands – what’s the difference and which do you recommend? +

The Cyclades offer iconic whitewashed villages, dramatic landscapes and longer open-water crossings - ideal for experienced cruisers and classic Greek scenery. The Saronic is calmer, greener and closer to Athens, with short hops between historic islands - perfect for relaxed sailing and families. We recommend based on your dates, group and pace.

03Can we visit Santorini, Mykonos, Naxos, or other specific islands in one week? +

Yes - within reason. A one-week route comfortably covers a cluster of nearby islands. Combining far-apart highlights (e.g. Mykonos and Santorini) is possible but means longer sailing days. We’ll design a realistic route that includes your must-see islands without rushing.

04What happens if the weather is bad? Will the trip be canceled? +

Trips are very rarely canceled. The captain monitors conditions daily and adapts the route to keep you in sheltered, comfortable waters. Safety and enjoyment always come first, and the flexible itinerary means there is almost always a great alternative nearby.

05Are prices per person or for the entire boat? +

Prices are for the entire boat - you charter the whole catamaran for your group, not per person. This makes it excellent value for families and groups of friends sharing the experience.

06What additional costs should we expect beyond the yacht price? +

Typical extras include fuel, marina/port fees, food and drinks, and the crew gratuity. We provide a clear breakdown in advance so there are no surprises, and you can choose your provisioning and dining preferences.

07How many islands will we visit during the week? +

Usually 5–7 islands or anchorages in a week, depending on distances and your pace. We balance moving and relaxing so you experience variety without spending all day at sea.

08Can we decide where to stop each day, or is it decided in advance? +

Both. We agree a flexible plan before departure, then fine-tune it day by day with your captain based on weather and what you’re enjoying. You stay in control of your holiday.

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Contact usSend an enquiry, a real advisor replies personally Arrange a video callPick a time that works for you Call us+30 693 723 4566 WhatsApp usAlso available on the same number

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