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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

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

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€950

€760

Per person

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From the Aeolian Islands to La Maddalena, passing through the Amalfi Coast and the Pontine Islands

Italy: Northern Sardinia

7 days - 7 nights

One departure available

August

€900

€810

Per person

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4.3

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE

Caribbean: Saint Martin

6 days - 7 nights

57 departures available

January - December

Starting from

€1,125

€1,013

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

10 departures available

July - October

Starting from

€1,260

Per person - min 2 pax

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4.6

5 days in Costa Smeralda and northern Sardinia

Italy: Northern Sardinia

4 days - 4 nights

3 departures available

July - August

Starting from

€850

Per person

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Paradise Seychelles by sailing catamaran

Indian Ocean: Seychelles

7 days - 7 nights

2 departures available

November - December

€1,450

Per person

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4.3

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Guadeloupe

6 days - 7 nights

55 departures available

January - December

Starting from

€1,125

€1,013

Per person

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4.3

Premium

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

Caribbean: Bahamas

6 days - 7 nights

8 departures available

July - December

Starting from

€1,865

Per person

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5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Caribbean: Guadeloupe

7 days - 7 nights

21 departures available

January - December

Starting from

€1,272

Per person - min 2 pax

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€2,100

€1,995

Per person

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4.8

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,200

Per person

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4.9

From the Lighthouse to the Volcano: sailing from Gibraltar to Lanzarote by catamaran

Spain: Andalusia

7 days - 7 nights

One departure available

November

€1,300

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

1046 reviews

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The magic of the Egadi Islands aboard a brand new catamaran

07/16/2025

Roberta M.

-

Italy

Thanks to Timoti, aka Captain (skipper), and Giuseppe's team for this fantastic experience. What can I say, the Egadi islands are wonderful and certainly do not need my praise. It was my first holiday at sea, and I doubt it will be my last! The catamaran was comfortable and well designed: with six people (including the skipper), you never feel cramped. Everything is functional and in very good condition — it really feels like new, or at least maintained with great care. If we want to be really picky, perhaps we could find a better way to create a little more storage/space in the sleeping cabins (for example, a shelf near the side/head of the bed of those who do not have access to the bedside table), always accepting the limitations of the structure. And for those who are new to this type of experience, it might be useful to receive the famous shopping options list in advance, so you already arrive with some ideas on the first day. It is absolutely not meant to be a criticism, but a constructive suggestion to make an already fantastic experience... even better! Special thanks to Timoti: in addition to being very nice, present, full of ideas and suggestions but always discreet and helpful, he also improvised himself as a chef, cooking real delights – from tuna tartare to an amatriciana with a bacon that cannot be explained!
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Dream sailing on a fully-equipped catamaran

07/16/2025

Alessia P.

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Italy

THE MOST RELAXING HOLIDAY I'VE EVER HAD. Comfortable boat equipped with everything, large and well-kept spaces! The highlight of the experience is definitely the crew: The captain very experienced and very nice, shared every decision with the group and cheered us up with his stories from all over the world; Cris, his trusted right-hand man, always operational and patient ready to meet the requests of the whole group. AUTHENTIC EXPERIENCE. I RECOMMEND IT WITHOUT ANY DOUBT
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North Sardinia and South Corsica by catamaran with flybridge

07/14/2025

francesca f.

-

Italy

The boat was very nice, comfortable and spacious. The environment is clean. The kitchen is large and comfortable. The only drawback: this type of boat does not offer great fun while sailing because it is not always possible to hoist the sails... Comfort is preferred to sailing. Antonio was a very good skipper, careful to meet the multiple needs of the whole crew. He made us discover wonderful places that will remain in our hearts.
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Magical Aeolian Islands by catamaran

07/14/2025

Ciro C.

-

Italy

Amazing skipper,, cook and boat

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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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