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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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4.8

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

September - October

Starting from

€950

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

5 departures available

August - November

Starting from

€1,455

€1,382

Per person

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4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

Starting from

€950

€760

Per person - min 2 pax

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4.8

Super!

Dream sailing on a fully-equipped catamaran

Italy: Southern Sardinia

7 days - 7 nights

2 departures available

August - September

Starting from

€850

Per person

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4.9

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€870

Per person

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4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

September - October

Starting from

€1,800

Per person

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4.8

Super!

Egadi Islands by catamaran with stewardess and cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

September

Starting from

€1,100

Per person

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4.3

Premium

GRENADINES 11 days on a ALL INCLUSIVE catamaran with hostess/cook

Caribbean: Grenadines & Martinique

9 days - 10 nights

47 departures available

January - December

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.3

Premium

Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Grenadines & Martinique

6 days - 7 nights

68 departures available

January - December

Starting from

€1,250

€1,125

Per person

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4.9

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€1,450

€943

Per person

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4.3

Premium

PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

Indian Ocean: Seychelles

7 days - 7 nights

66 departures available

January - December

Starting from

€1,760

€1,584

Per person

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4.6

From Kos to Rhodes on my catamaran

Greece: Dodecanese

7 days - 7 nights

One departure available

August - September

€980

€784

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

1174 reviews

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Discovering the Aeolian Islands by catamaran with hostess

08/29/2025

Alessandro D.

-

Italy

Unfortunately the organization of the catamaran was absolutely not up to the wonderful place that are the Aeolian Islands: - Daniele, the reference of the holiday on the booking page, not received like anyone else from the organization, except Valentina who was not of great help when we needed it; - All the equipment of the catamaran, which we paid for and had to be included in the experience, was not present. Snorkeling gear, fishing gear, BBQ, drone, water toys, and Wi-Fi were not there. They replied that after washing the boat they didn't remember to put them back on board (it seems rather unlikely to me as an excuse). And in any case, no one has deigned to apologize or consider a partial refund even as a gesture; - the bathrooms of the catamaran, in 2 cabins, never worked properly from the first moment and were clogged 3 times (obviously we know boats and we know that you should not throw anything into the toilets, and these were malfunctioning from the beginning); - in check-in and check-out we needed a trolley to transport the luggage of the whole crew to the port and obviously no one from the organization provided us with any trolley, nor did they reveal themselves; The only really positive note: skipper Gianluca and his wife Ylenia. Gianluca is an exceptional captain who has been able to solve all problems from the beginning of the holiday to the end, always sailing safely but also showing himself very willing to take us with the tender to the various coves of each island. Ylenia cooked divinely and was always kind and super helpful. In summary, the Aeolian Islands are a beautiful place to explore by boat/catamaran, but we absolutely do not recommend relying on this organization/company that has not proven to be even remotely up to expectations.
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/28/2025

Gloria G.

-

Italy

Fantastic experience made special by the people we met on the boat and our skipper who made sure that the trip was 'carefree'! The flotilla is the right way to have fun and relax, sharing it with all the boats and personal moments with your sailing companions! In short, everything you need for a perfect holiday!
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Different Flotilla: Party and new friends in the Aeolian Islands

08/28/2025

Giorgio V.

-

Italy

One of the best holidays of my life! Let's start with the crew to whom all my affection goes because we left as perfect strangers and returned as a family. Skipper Fabio is a true friend: he was able to deal with all situations and always made us feel his boating experience, both when we sailed and in the most difficult moments such as moorings in port. The boat was the premium version, just a few small flaws on the cabin with the bunk bed that would be sold separately at perhaps lower prices and on the lack of some blankets on board! For the galley when they recommended the list perhaps there were many useless things: look carefully and decide with the crew what to buy. The tour of the Aeolian Islands was fantastic, the weather allowed us to do almost everything that was planned, all that was missing was a party with the boats anchored in a circle (star) but on the other hand we had a beautiful aperitif in Panarea and toured the streets of Salina and Lipari. The organization was up to one of the most beautiful holidays of my life. Keep up the good work and get better and better every time! Fair winds, Giorgio.
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/28/2025

Sara R.

-

Italy

We had an unforgettable holiday at the Pontine Islands! The skipper Antonello proved to be truly exceptional: professional, competent and always attentive to safety, but also nice and helpful, which made the experience even more enjoyable. The islands are stunning, with hidden coves, crystal clear waters, and stunning sunsets. The boat was comfortable and well organized, perfect for experiencing the sea in total relaxation. Every day was a mix of adventure, discovery and moments of pure peace. I absolutely recommend this experience to anyone who wants to experience the Pontine from a unique perspective: thanks to Antonello we felt in excellent hands and we will take home precious memories.

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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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