header cover

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.

77

experiences

cover image
avatar image

3.1

Greece Cruise in the Sporades - 2 Catamarans & 1 Sailboat

Duration:

9 days - 10 nights

Greece:

Sporades

avatar placeholder
avatar placeholder
avatar placeholder

+6 travellers

have booked

Starting from

€1,640

Per person

cover image
avatar image

4.6

Flotilla Different: Party and new friends in the Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar placeholder

+5 travellers

have booked

Starting from

€999

€1,175

Per person

cover image
avatar image

3.8

One way from Lošinj to Zadar

Duration:

9 days - 10 nights

Croatia:

Kornati Islands

Give this experience a try!

€1,200

Per person

cover image
avatar image

5.0

Island of Elba and North Corsica by Catamaran

Duration:

7 days - 6 nights

France:

Corsica

Give this experience a try!

€1,700

Per person

cover image
avatar image

4.7

The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands

Duration:

6 days - 7 nights

Italy:

Gulf of Naples

avatar image

Errico C.

has booked

Starting from

€999

€1,175

Per person

cover image
avatar image

4.6

Premium

Italy Experience - 8 giorni in catamarano ALL INCLUSIVE con hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Starting from

€2,890

Per person

cover image
avatar image

3.1

Greece Cruise to the Sporades - 2 Catamarans & 1 Sailboat

Duration:

10 days - 11 nights

Greece:

Sporades

avatar placeholder
avatar placeholder
avatar placeholder

+14 travellers

have booked

Starting from

€1,750

Per person

cover image
avatar image

4.7

5 days in Costa Smeralda and northern Sardinia

Duration:

3 days - 4 nights

Italy:

Northern Sardinia

Give this experience a try!

€900

Per person

cover image
avatar image

5.0

Esperienza sul catamarano TOP CLASS in Toscana e Corsica

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,352

€1,690

Per person

cover image
avatar image

4.6

From the Saronic Islands through in the Corinth Canal by catamaran

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€870

Per person

cover image
avatar image

4.7

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

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€1,796

€1,890

Per person

cover image
avatar image

5.0

Isole Eolie - Mare Sole e Relax su un nuovo e grande Catamarano Lagoon

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€1,170

€1,800

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

799 reviews

avatar placeholder

NATURE & RELAXATION - 7 days on a catamaran with hostess/sailor

03/25/2024

vincenzo P.

-

Italy

Ho fatto tante esperienze di questo genere ma quest’ultima organizzata veramente in maniera eccellente skipper all’altezza della situazione ,chef fantastica posto da sogno da consigliare a tutti
avatar image

PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

03/12/2024

Giancarlo A.

😍😍
avatar placeholder

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

02/19/2024

Klaembt R.

Boot ist ok, missing in the Night AC, during the day it works but in the Night??
avatar image

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

02/5/2024

MARIO I.

when I made the reservation I paid for a superior cabin and with the specific request written to you to have a bow cabin. I was assigned a central cabin, I would have liked an official communication from you, informing me of the availability or otherwise of the forward cabin and leaving me the free will to decide whether to accept or not, or withdraw from the contract for which I had paid. commercial and communication incorrectness

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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.

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964