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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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4.5

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

26 departures available

May - October

Starting from

€1,305

€1,044

Per person - min 2 pax

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4.5

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

44 departures available

January - December

Starting from

€1,680

€1,344

Per person - min 2 pax

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4.5

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

26 departures available

May - October

Starting from

€1,320

€1,056

Per person - min 2 pax

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4.6

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

One departure available

August - September

€1,290

€1,190

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

One departure available

September

€620

€558

Per person

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4.5

Premium

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

43 departures available

January - December

Starting from

€1,310

€1,179

Per person - min 2 pax

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4.9

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

€945

Per person

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New

Premium

All inclusive sailing cruise on Excess 11 Catamaran in Croatia with hostess

Croatia: Split Archipelago

7 days - 7 nights

One departure available

September

Starting from

€1,965

Per person

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New

Discover the Balearic Islands and their Calas aboard a trimaran

Spain: The Balearic Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€850

€765

Per person

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4.9

Aeolian Islands in a big and new catamaran: sea, sun, relaxation

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€980

Per person

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New

Discover the wonderful coasts and villages of the Balearic Islands by trimaran

Spain: The Balearic Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€850

€765

Per person

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4.5

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

2 departures available

September - October

Starting from

€1,485

Per person - min 2 pax

Why book a holiday with Sailsquare?

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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

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

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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

1457 reviews

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/30/2026

Beatrice G.

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IT

I recommend everyone to try a sailing holiday at least once because it is a truly beautiful experience. I had a fantastic week especially thanks to the group I was with, whom I thank because it was the people who made the holiday special. Unfortunately, however, the organization of Different Sailing was very disappointing and still has a lot to improve. We were not initially assigned the boat we had paid for, but a lower category one, and only after several complaints were we refunded. In addition, we have practically never done packages or parties all together, which are precisely the format and the strong point of a flotilla. Except for the last evening, each boat remained very isolated and this did not allow us to really get to know the people of the other boats. The program and organization seemed almost non-existent and even the DJ's music was always the same. Even the speech made at the beginning of the holiday regarding possible checks by the Guardia di Finanza left me rather perplexed. In conclusion, I am happy to have had this experience and I take home a beautiful memory thanks above all to the people I met, but from the point of view of organization there is still a lot to improve.
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Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

08/30/2026

Jacopo M.

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IT

If we could give more than 5 stars, we'd give Greg & Aga a hundred — without a second thought. The photos speak for themselves, but trust me, there's so much more behind them: outstanding professionalism, many years of experience at sea, natural empathy, and a warmth that wins you over from day one. Plenty of laughter, real attention to every little detail and to our every need, genuine respect for the environment and for the local culture, and an authentic joy in the small things that is always overwhelming and contagious. And the catamaran is stunning! Greg is simply fantastic — the kind of skipper you trust completely from the very first moment, without a shadow of a doubt. A week with them and you forget about everything else. Constantly spoiled by their care and by Aga's (& T's) excellent cooking, and by the sailing lessons of the best skipper out there — with days paced only by the sun and the wind, and stops in authentic places, far from the usual routes. And one thing says it all: everyone truly loves Greg & Aga. In every port, in every taverna, we always felt at home and part of the family. Hands down one of the best holidays we've ever had. Thank you for this wonderful week. Dobra & Yamas! 🇬🇷⛵
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/29/2026

Alberto Z.

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IT

Beautiful experience, excellent organization, thanks go to Simone for his commitment and dedication, as well as to the staff, the skippers and with praise for our Pablito, good both at sea and in the console. A holiday not so suitable for those seeking relaxation 😎

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/29/2026

Mattia F.

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IT

The holiday overall was fun, especially thanks to the group I was on the boat with, with whom I got along very well. However, from the point of view of the organization of the flotilla, there are several aspects that in my opinion should be improved. A lot of time was lost from check-in and I had the feeling that some situations were not handled in a particularly coordinated way. Even the first dinner, proposed at € 25, did not seem adequate to the price paid: probably, knowing in advance exactly what would be offered and at what price, we would not have accepted it. The skippers were good and helpful, but I found little involvement in really creating a flotilla dynamic. During the day the boats spent a lot of time sailing separately and there were few opportunities to get together and get to know each other. Even in the evening, very few events or common moments were organized for the whole flotilla. Personally I would have preferred to do many more packages/stars during the day and evenings together and, above all, get to know the people of the other boats more. Even some of the most beautiful coves, such as those of the Faraglioni di Lipari, in my opinion have not been exploited well: in some places we have stayed too little time, giving again the feeling of a non-optimal management of time and travel. Another aspect that I found particularly problematic concerns the issue of the licenses of some skippers. I was told that some did not have the necessary license to play the role of skipper towards people they did not know. I find this situation not very reassuring, especially considering that the holiday had been paid regularly and in full. The fact that, in the event of a possible check, there was even the need to provide an untruthful version of the facts to the Guardia di Finanza is, in my opinion, something to be absolutely avoided and clarified before departure. The number of people per boat also seemed excessive to me. We were 13 people on a sailboat, a number that I found uncomfortable and which, from what I had read in the description of the holiday, did not correspond to what I expected. In addition, skipper and co-skipper slept in the saloon and the additional berth was in fact sold, despite it being a space that I found practically unlivable. On a holiday of this type, comfort on board should be considered a fundamental aspect. Ultimately, I had fun and I take home a good memory especially thanks to the people I shared the boat with. However, precisely because the flotilla format seemed very interesting to me, I expected greater organization and above all greater involvement between the different boats. In my opinion there is a lot of potential and you can improve a lot with a little effort from Different Sailing. I understand that managing a large flotilla is not easy: 10 boats and about 120 people are really a lot. Precisely for this reason, however, I believe that even more accurate planning and coordination are needed, in order to really create the flotilla spirit and not find ourselves, for most of the day, with each boat proceeding on its own.

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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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