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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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4.7

Super!

Luxury catamaran cruises in the Greek islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

September - November

€1,000

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€945

Per person

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4.7

Super!

Greek Islands Catamaran Cruise - Saronic

Greece: Saronic Islands and Athens area

7 days - 7 nights

7 departures available

August - October

Starting from

€820

Per person

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5.0

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

5 departures available

September - October

Starting from

€212

€191

Per person

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4.9

Egadi Islands by catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€1,100

Per person

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4.5

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

One departure available

October

Starting from

€1,320

€1,056

Per person - min 2 pax

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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

2 departures available

August - October

Starting from

€1,305

€1,044

Per person - min 2 pax

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New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

35 departures available

August - September

Starting from

€170

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

3 departures available

August - September

Starting from

€1,000

€850

Per person

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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

45 departures available

January - December

Starting from

€1,680

€1,260

Per person - min 2 pax

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New

Slow sailing in Portoferraio - daily trimaran trip

Italy: Tuscany

1 day - 0 nights

One departure available

August

€80

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

2 departures available

August - September

Starting from

€1,924

Per person

Why book a holiday with Sailsquare?

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

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

1365 reviews

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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/16/2026

Leonardo F.

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IT

The actual duration was not 7 days but 6 considering that we boarded on Saturday at 17:00 (remaining in port until Sunday morning) and disembarked the following Saturday at 9:00 (returning to port at 17:00 on Friday). Even on the nights you have to consider that two of the seven are in the port of departure... In short, everything was fine, I would have made the most of at least the whole last Friday, staying to sleep in the roadstead and returning to port early Saturday morning.

The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/16/2026

Ezio

Overall a great experience that I would do again.

The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/16/2026

ROBERTA N.

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IT

Perfect holiday from all points of view: 8 days by catamaran from Marina di Scarlino to the north of Corsica and back. There was a perfect balance between relaxation, sea, aperitifs and parties. I left without knowing anyone and ended up laughing and having fun all day, every day! The catamaran was beautiful, clean, spacious and equipped with all amenities including, air conditioning, watermaker and fantastic sun nets. It was wonderful to share aperitifs, parties and moments at sea and on land with all the participants of the flotilla. We met dolphins 2 times and saw the eclipse at sunset... what can I say... moments that I will always remember! A special thanks to Alessio, our impeccable skipper, Orlando, Daniele, Vladimiro, Antonio and Andrea who made this flotilla special. Thanks also to Giovanni, super helpful from the first contact. I will carry in my heart all the emotions of this wonderful holiday♥️⛵️
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/16/2026

Francesco V.

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IT

The only flaw is to make the boat more involved in the choices of the flotilla for the rest very very well

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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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