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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!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

3 departures available

August - September

Starting from

€1,100

Per person

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4.8

Super!

Croisières en catamaran de luxe dans les îles grecques

Greece: Saronic Islands and Athens area

7 days - 7 nights

18 departures available

May - November

Starting from

€1,000

Per person

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4.8

Super!

Catamaran with Chef in the magical sea of the Ionian Islands - Holiday for SINGLES

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,450

Per person

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4.9

Egadi Islands by catamaran with hostess/cook on board

Italy: Aegadian islands

7 days - 7 nights

2 departures available

June - August

Starting from

€1,100

Per person

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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

23 departures available

May - October

Starting from

€1,320

€1,188

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

7 departures available

June - September

Starting from

€945

Per person

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4.4

Premium

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

Caribbean: Saint Martin

6 days - 7 nights

23 departures available

May - December

Starting from

€1,205

€1,085

Per person - min 2 pax

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4.4

Premium

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

Caribbean: Grenadines & Martinique

9 days - 10 nights

22 departures available

May - December

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.9

Catamaran between Costa Smeralda, Maddalena and Bonifacio!

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

June - August

Starting from

€1,020

Per person

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4.4

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

33 departures available

May - December

Starting from

€1,250

€1,125

Per person - min 2 pax

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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

4 departures available

June - July

Starting from

€1,100

Per person

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4.4

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

18 departures available

May - October

Starting from

€1,525

€1,373

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.

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

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

1298 reviews

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

05/9/2026

Giorgia P.

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Italy

Very nice catamaran even if there were not enough bottles of wine on board among those we requested. Skipper good but preferred to speak in French and often did not adapt to the requests of us passengers. Nice itinerary but there is not much coral reef and fish, compared to other destinations. Very long crossings between one island and another and with always very rough seas.
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Sailing among the Myths: The Pontine Islands by Catamaran

05/9/2026

Giorgio D.

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Italy

Beautiful weekend, but much of the credit certainly goes to Alessandro, a skipper capable of transforming a simple experience at sea into something that stays with you. Professional when needed, but above all human, genuine and capable of creating a group without ever forcing anything. He made us all feel at ease from the first moment, with that intelligent lightness that is rare to find today. Always attentive, helpful and with a calm that conveys safety even to those who may not be used to life on a boat. Between laughter, sunsets, chats and simple moments, he managed to create that atmosphere that really makes you disconnect from the routine. Super recommended experience... and skipper who really makes a difference. Thank you Ale, because the sea is beautiful... But the right people make it unforgettable
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LAST MINUTE - April 25th and May 1st in FLOTILLA in the Seychelles

05/5/2026

Giovanni M.

-

Italy

It was my first experience with Marmaglia and I must say that they are excellent: from an organizational point of view, problem solving and performance management. Excellent in terms of coordinating the skippers and the activities planned in the itinerary. On the next sailing trip, I will look at their travel offers first.
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

05/4/2026

Anna Maria M.

-

Italy

A week based entirely on navigation, with little time for snorkeling. Obligatory, prepaid shore trips that were worth just a great lobster lunch on the beach. Rigid aperitif times, lunch and dinner, inflexible cook on the menu chosen at his unquestionable will. No possibility of changing the menu of the day, because it was not declared before and therefore sometimes we were left without being able to eat. Tense atmosphere if you didn't like the food or had requests, also due to linguistic misunderstanding. The crew spoke only French, no English or little. The quality of the wine and food is low. Frozen fish in bags, except on the first day. Cocktails that are good only on two or three occasions, because they are freshly prepared. For the rest, bottles of rum and fruit already prepared and hot. Disappointing holiday despite the very beautiful location.

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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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