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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.

74

experiences

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5.0

One Way Holiday from the Pontine to the Aeolian Islands by Catamaran

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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+5 travellers

have booked

€1,150

Per person

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4.9

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+65 travellers

have booked

Starting from

€790

Per person

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All-inclusive cruise in the archipelago of La Maddalena

Duration:

8 days - 7 nights

Italy:

Northern Sardinia

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+6 travellers

have booked

€1,700

Per person

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4.0

Magical Aeolian Islands by Sailing Catamaran

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+7 travellers

have booked

Starting from

€1,300

Per person

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Discovering the Aeolian Islands by Catamaran

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+9 travellers

have booked

Starting from

€1,300

Per person

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4.6

Premium

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

Duration:

6 days - 7 nights

Croatia:

Split Archipelago

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Francesco L.

has booked

Starting from

€1,590

Per person

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4.6

A real sailing trip, archaeological sites and beaches between Zakynthos and Athens

Duration:

7 days - 7 nights

Greece:

Peloponnese

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+3 travellers

have booked

€750

Per person

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The enchantment of the Egadi Islands: an unforgettable catamaran trip

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€675

Per person

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4.5

1 Week Professional Catamaran Training - Cagliari Sardinia

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€1,320

Per person

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4.7

Big and luxurious 60ft catamaran in Saronic, the best local experience

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+10 travellers

have booked

Starting from

€1,499

Per person

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4.6

Premium

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

Duration:

6 days - 7 nights

Caribbean:

Bahamas

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+18 travellers

have booked

Starting from

€1,350

Per person

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4.6

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Guadeloupe

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+2 travellers

have booked

Starting from

€1,150

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

827 reviews

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

06/11/2024

Verena R.

It was a great katamaran trip with delicious food, excellent places and nice people! We really enjoyed our trip! :)
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Weekend catamaran in Portovenere and Cinque Terre

06/10/2024

Massimo P.

-

Italy

È stata un'esperienza meravigliosa che conto di ripetere. Antonio è una persona davvero piacevole e la sua Cassiopea un'imbarcazione accogliente, pulita e ben organizzata.
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Weekend catamaran in Portovenere and Cinque Terre

06/10/2024

Anto B.

Non dò 5 stelle solo perché c'era poco vento e quindi si può dire non abbiamo quasi mai veleggiato ma, per il resto tutto fantastico. Un Capitano con C maiuscola, numero 1!!! Imbarcazione fantastica. Assolutamente da rifare!
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Weekend catamaran in Portovenere and Cinque Terre

05/27/2024

roberta r.

-

Italy

Antonio é uno skipper simpaticissimo e di esperienza! Ci siamo divertiti molto insieme e spero di poter tornare a navigare con lui sul suo meraviglioso catamarano. Sempre molto disponibile e con lui il tempo é volato!

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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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