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Catamaran yacht sailing holidays & skippered tours

Discover the magic of skippered catamaran holidays, an original holiday idea to share a comfortable adventure with family or friends in a little bit of luxury. Catamaran holidays in the Caribbean including the Grenadines, Seychelles, Martinique, Antigua and Barbuda, and Cuba - as well as in the Mediterranean including Greece, Croatia, Corsica, and Sardinia. The world’s best travel destinations await you.

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

16 departures available

May - October

Starting from

€950

Per person

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4.8

Super!

Greek Islands Catamaran Cruise - Saronic

Greece: Saronic Islands and Athens area

7 days - 7 nights

23 departures available

April - October

Starting from

€820

Per person

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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

28 departures available

April - November

Starting from

€1,550

€1,473

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€1,020

€918

Per person

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4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

14 departures available

May - October

Starting from

€2,400

€2,160

Per person

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5.0

Super!

Ionian Greece aboard a Catamaran with Skipper/Chef

Greece: Ionian Islands

6 days - 7 nights

4 departures available

July - August

Starting from

€1,900

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

11 departures available

June - September

Starting from

€800

Per person

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4.8

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

June - September

Starting from

€1,100

Per person

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4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

July - August

Starting from

€1,450

Per person

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4.8

Super!

From Lipari to Palermo: magical week on a catamaran with a hostess

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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4.8

Super!

From Marsala to Palermo: magical week on a catamaran with hostess

Italy: Aegadian islands

7 days - 7 nights

One departure available

May - June

€850

Per person

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4.8

Super!

Magical Week of Wellness Yoga, Cooking, Health, and Relaxation

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,000

Per person

Why book a holiday with Sailsquare?

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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Catamaran yacht sailing holidays & skippered tours

1291 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

04/16/2026

DONATELLA D.

-

Italy

My rating is just enough and I would actually only give it 2 stars. Unfortunately the holiday turned out to be far below expectations, the quality / price ratio is very bad. First of all, the French skipper who speaks almost no English is unacceptable with a group of guests from various nationalities. In case of emergency, the captain must know how to give clear and quick orders and he would not have been able at all. The French hostess (his girlfriend) cooked everything except "navigation" food: for the whole holiday as vegetables only two salad leaves and one evening green beans, in the first three days there was practically no fruit and in the tropics it is a must, fish eaten only twice and meat after all; he always cooked heavy lunches / dinners that did not go well with the environment and the temperature ... The answers to the various intolerances or requests for vegetarian dishes were rude and considered only sometimes. The group we sailed with fortunately turned out to be the trump card of the holiday, we were all on the same wavelength and complained about the same things. Our collective requests to stay a little longer in one place or to change times for activities have never been answered in the affirmative, revealing an excessive rigidity on the program and on the needs of the captain-hostess as a couple. Another sore point is navigation: 13 hours at night as soon as you embark and then immediately "segregated" in the cabin with the order not to leave until 6 in the morning is madness. In our group two people were sick, one of whom was in a single cabin and neither the hostess nor the captain bothered to go and check on her and give her a hand in case of need. Unfortunately, even the places visited are below expectations: obviously they are beautiful places, but as far as coral reefs and marine fauna are concerned, they are very lacking. They made us do 2-3 snorkeling in very busy places (a little bit for a week on the boat). The cleanliness left a bit to be desired and note that the cabin has to be cleaned by itself throughout the week. Basically I loved the catamaran and the holiday at sea but there were too many poor points so in the future I will definitely evaluate other destinations and modalities.
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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

04/3/2026

gulce c.

-

Türkiye

It was wonderful, thank you !
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

03/31/2026

Roberto C.

-

Italy

An unforgettable experience thanks also to the whole team, both organizational and on the boat. Highly recommended tour, perhaps to be tackled with a few more days on the boat to avoid long crossings back.
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Under the Caribbean sun on a catamaran

03/10/2026

Irene B.

-

Italy

The boat is very beautiful, well maintained and equipped with many comforts, and this makes your stay on board pleasant. The itinerary is also interesting, but with elements to take into consideration: several hours of navigation are planned (about 12 on the first day and 6 on the second, as well as similar times in the last days of return). In addition, these are areas where, once you arrive in the evening, it is not always easy to experience the place: many merchants close as early as around 9 pm, so the opportunities to explore on land are limited. The crew proved to be competent and attentive to the safety of navigation, with attention to detail during meals and attention to everyone's dietary needs. However, in general, it would have been appreciable to have more involvement of guests in the small choices of the week (such as the organization of the day and activities). A more proactive approach to sharing information and opportunities would have made the experience even more enjoyable and participatory. The same principle would also apply to the management of the common fund (€ 600 per person), of which we did not have visibility during the week. An episode related to the blockage of the toilet was also handled in disrespectful tones and with an immediate attribution of responsibility, before the technical cause of the problem was clarified. The solution was to use the bathroom of the other guests, which was only made possible thanks to the climate of collaboration between us participants. Again, a more balanced approach to managing the situation would certainly have been appreciated. Overall, an experience with several positive aspects, but with some room for improvement in the management of communication and relationship with guests.

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7 reasons to go on a sailing holiday on a catamaran with a skipper

  • A catamaran is described by many as a floating house: comfortable, spacious, bright, and very well equipped.
  • Ideal for families with children, with room and the environment that is more secure than a monohull sailboat.
  • A new way of travelling that allows you to discover islands and paradisiacal beaches that are only accessible by boat - the catamaran has a weak draft, allowing it to go where other boats cannot.
  • The opportunity to get stuck into a book, nap on the deck with a warm sea breeze, or trampoline on the netting that sits at the front of the boat.
  • A catamaran is more stable than a sailboat, therefore they are a great way for first time sailors to discover the magic of sailing holidays, without the fear of seasickness!
  • A catamaran usually has 4 large cabins, which will allow you to cast off with your family or your best friends, with plenty of space for all.
  • The best way to discover the exotic islands of the Caribbean, including the Grenadines, Martinique, Guadeloupe, Cuba, and the British Virgin Islands.

Everything you need to know to organise your next catamaran sailing holiday

The advantages of a catamaran sailing holiday with Skipper

If you have an existing group of travellers (of family or friends), we highly recommend reserving an entire catamaran with skipper. In such cases, it is often possible to receive a discount on you booking (from 10% of the total booking cost upwards), this is more likely to be the case if you are booking in advance or in less busy periods of the year. In addition to saving money, reserving a skippered catamaran allows you maximum flexibility in itineraries, with skippers often willing to be very accommodating to your wishes. Reserving a whole catamaran also allows maximum privacy, if you are looking to share some quality time with your family or friends.

If you are travelling as a couple or solo, bare in mind that you can book either a single berth or an entire cabin. A cabin allows for much more privacy and more personal space. Either way, you have the ability to share your sailing experience with other like-minded travellers - an excellent opportunity to meet new people and make new friends!

Catamarans: the comfort of a house, on the water!

Many describe catamarans as floating houses, for the extensive space and facilities they have onboard. After a long day of adventure, you can rest in large, well-equipped cabins, that are complete with a full size double bed. There are usually 2 cabins each for the 2 floats, or sides of the boat. These are then separated by a bathroom, complete with a shower and toilet. The common area of the catamaran including the lounge and kitchen are then located in the middle-upper part of the boat, in between each float.

Catamarans are generally very spacious and bright, with large windows that overlook the sea, a perfect view when cooking or relaxing! They are very social and friendly due to how the design of the boat. Finally, it is true that the bridge offers lots of charm to the catamaran, this area of the boat is the main area for relaxing and enjoying time on the deck!

What are the differences between a sailboat or catamaran?

A sailboat may be better for people looking to learn the practice of sailing, or to sharpen their skills, where as the catamaran is the most comfortable and luxurious way to enjoy a holiday at sea. Here are a few advantages and disadvantages of each:

Sailboat: ideal for sailing, less emphasis on comfort, cheaper, less spacious, more user-friendly

Catamaran: less motion impact on the stability of the boat, more comfortable, more expensive, more spacious

The 8 best destinations for a catamaran sailing holiday

The Mediterranean, Caribbean, Indian oceans - some destinations are ideal for a skippered catamaran sailing holiday. For those who dream of a trip in the Caribbean, it is full of ideal different destinations for a catamaran trip. We mainly recommend the Grenadines (which normally set sail from the port of Marin in Martinique), Guadeloupe, and Cuba.

The Mediterranean Sea is another paradise for catamaran trips. We recommend a week between Corsica and Sardinia to explore the famous Lavezzi Islands and the Maddalena Archipelago, but there is also the wonderful Greek archipelago of the Cyclades or the Ionian Islands. Last but not least, who does not dream of discovering the paradisiacal landscapes of Seychelles aboard the catamaran with a local skipper? An adventure to treasure for your entire life.

All you need to know for your next skippered catamaran cruise

The demand for skippered catamaran holidays can be very high compared to the number of offers. We recommend booking several months in advance - January or February for summer trips in the Mediterranean and September or October for winter trips in the Caribbean.The best time for a catamaran holiday in the Mediterranean is from May to October. For a Caribbean holiday, between November and April.

The price of a catamaran sailing holiday can be much higher than a sailing holiday on a monohull because of the extra comfort and the limited availability. You can find experiences between €600 and €1,200 per week depending on the destination and the period of the year.

The best destinations for catamaran holidays are: Antilles (Grenadines, Guadeloupe, Cuba, British Virgin Islands), Seychelles and the Mediterranean (Greece, Corsica, Sardinia, Croatia). Booking an entire catamaran with a skipper is a brilliant option for holidays with family or friends.

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