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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.

36

experiences

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4.0

1 week professional catamaran training - Marina San Miguel - Tenerife

Duration:

7 days - 7 nights

Atlantic islands:

Canary Islands

Be the first one to book!

Starting from

€1,426

Per person

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4.2

Premium

PHUKET Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Thailand:

Phuket, Krabi and Phi Phi Islands

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+6 travellers

Have booked

Starting from

€1,905

Per person

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4.2

Premium

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

Duration:

7 days - 7 nights

Caribbean:

Saint Martin

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+2 travellers

Have booked

Starting from

€1,630

Per person

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4.2

Premium

TORTOLA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

BVI - British Virgin Islands

Starting from

€1,760

Per person

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4.2

Premium

BORA BORA Dream - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Pacific Ocean:

French Polynesia

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+2 travellers

Have booked

Starting from

€1,280

Per person

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4.2

Premium

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

Duration:

7 days - 7 nights

Caribbean:

Bahamas

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+16 travellers

Have booked

Starting from

€1,795

Per person

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4.2

Premium

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

Duration:

7 days - 7 nights

Caribbean:

Grenadines & Martinique

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+2 travellers

Have booked

Starting from

€1,560

Per person

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4.2

Premium

GUADELOUPE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

Guadeloupe

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Fabian M.

Has booked

Starting from

€1,320

Per person

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4.2

Premium

MALDIVES Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Indian Ocean:

The Maldives

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+2 travellers

Have booked

Starting from

€1,230

Per person

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4.2

Premium

PRASLIN Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

Duration:

7 days - 7 nights

Indian Ocean:

Seychelles

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+12 travellers

Have booked

Starting from

€1,720

Per person

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4.2

Premium

Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

10 days - 10 nights

Caribbean:

Grenadines & Martinique

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+14 travellers

Have booked

Starting from

€2,055

Per person

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4.2

Premium

SILHOUETTE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

Duration:

10 days - 10 nights

Indian Ocean:

Seychelles

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+2 travellers

Have booked

Starting from

€2,235

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

776 reviews

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Cous cous festival and Egadi islands, Scopello in Catamaran! One way with cook on board

10/2/2023

Monica C.

Francesco....consigliato....professionale e competente oltre che do compagnia. Vacanza stupenda
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Sun & Fun Rabble Flotilla - Ionian Greece

10/1/2023

Milena M.

-

Italy

Marmaglia è la svolta! Tutto ciò che vi auguro di incontrare nella vita. Questa estate in Grecia mi sono divertita moltissimo. Ho fatto parte di un gruppo di 70 persone che, suddivise tra 6 barche a vela e 1 catamarano, ha visitato le Isole ioniche la settimana di ferragosto. Michele e gli altri skipper (mio preferito del cuore Alessandro S.C.) sono riusciti a garantirci posti eccezionali, rade "private" e tanto divertimento. Personalmente sono molto soddisfatta di questa vacanza, tanto da averne già prenotata un'altra "a terra" sempre con marmaglia. Consigliatissimo partire con loro, non ve ne pentirete!
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Experience the Egadi Islands aboard a 2020 catamaran with Hostess

09/28/2023

PAOLA R.

-

Italy

Giuseppe, disponibile e sorridente in ogni situazione, non si può volere nulla di più
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The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands in CATAMARAN

09/27/2023

Giulia P.

Inizierei con un"CHE MERAVIGLIA LA FLOTTIGLIA!".Il mio viaggio in catamarano è stato un'esperienza emozionante e indimenticabile.Partire con un gruppo di 10sconosciuti poteva sembrare intimidatorio all'inizio ma si è rivelato essere un'avventura straordinaria.Il primo impatto con il catamarano è stato a dir poco WOW.Il nostro skipper, Andrea,ha subito creato un'atmosfera accogliente e la sua conoscenza del mare e delle isole che stavamo per visitare ha reso il viaggio ancora più interessante.Abbiamo visitato isole meravigliose esplorando baie e spiagge ma anche scendendo a terra ogni giorno.Le giornate a bordo erano piene di risate, chiacchiere e brindisi no stop.Nonostante fossimo un gruppo di estranei all'inizio,abbiamo rapidamente legato, condiviso esperienze e storie di vita sotto cieli stellati. Difficile spiegarlo a parole.è stata più di una vacanza.Grazie Andrea per averci accompagnato e grazie La Flottiglia per queste giornate meravigliose che conserverò per sempre nel cuore.

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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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