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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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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

10 departures available

August - November

Starting from

€1,640

€1,558

Per person - min 2 pax

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - October

Starting from

€950

€855

Per person

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4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

8 departures available

August - October

Starting from

€2,500

€2,250

Per person

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4.6

North Sardinia and South Corsica by catamaran with flybridge

Italy: Northern Sardinia

7 days - 7 nights

3 departures available

August - September

Starting from

€1,290

Per person

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4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

6 departures available

August - November

Starting from

€1,000

Per person

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New

Ibiza and Formentera: the best of the Balearic Islands by catamaran

Spain: The Balearic Islands

6 days - 7 nights

2 departures available

August

€1,350

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€1,020

Per person

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4.8

Super!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

2 departures available

September

Starting from

€1,050

Per person

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4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

August

Starting from

€1,800

€1,440

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

4 departures available

August - September

Starting from

€850

Per person

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4.6

Capri, Ischia and Amalfi Coast by catamaran with hostess and cook

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€1,990

Per person

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4.8

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

August - October

Starting from

€900

Per person

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

1318 reviews

North Sardinia and South Corsica by catamaran with flybridge

07/26/2026

Loredana R.

-

IT

The skipper Chiara top, the Tour we did was wonderful, for The boat of the Sore notes, door of the Broken bathroom and we had problems with the bathroom once fortunately then solved by the skipper
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Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

07/26/2026

Massimiliano B.

-

IT

Massimo and Andrea are a mix of competence, calm and sympathy. The catamaran is a great option to enjoy the sea and comfort. The Saronic islands are a very pleasant discovery.

Comfortably Aeolian Islands: Catamaran Cruise with Steward

07/25/2026

Lorena R.

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IT

The experience was wonderful. We sailed with the skipper Giorgio who was always available, sensitive to our every need. The enthusiastic, proactive and passionate cook Diego delighted us with his cuisine and took care to satisfy my need not to eat fish. We were also lucky to have met excellent travel companions. Experience to be repeated. Aeolian Islands, a paradise.
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Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

07/25/2026

Matthias S.

-

IT

From the moment we stepped aboard [hidden] Cat, Aga and Greg made us feel like welcomed friends rather than guests. Aga is so much more than an incredible cook—she is an exceptional host. She has a genuine talent for making everyone feel comfortable and cared for. She was endlessly patient, always checking that everyone was happy, explaining everything with a smile, and creating such a warm, relaxed atmosphere on board. Every meal she prepared was fresh, healthy, and absolutely delicious. We ate incredibly well all week! Every single ingredient is organic fresh and simply delicious 😋 Greg was equally fantastic. He was always positive, calm, and professional, giving us complete confidence from the moment we set sail. We trusted him completely and always felt safe, whether we were sailing between islands or spending the night anchored in peaceful, crystal-clear bays. One of the most magical parts of the trip was sleeping at anchor under the stars and waking up surrounded by the sea. Greg and Aga took us to stunning hidden islands and secluded coves that we never would have discovered on our own—beautiful, authentic places far from the usual tourist crowds. The catamaran itself was extremely comfortable, very well equipped, and impeccably maintained. We slept wonderfully every night and had everything we could possibly need on board. Greg and Aga are wonderful people, outstanding hosts, and they made this one of the best holidays we’ve ever had 🐬😍💙🧿

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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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