header cover
logo

Log in

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.

cover image
avatar image

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

5 departures available

September - October

Starting from

€2,150

Per person

cover image
avatar image

4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

2 departures available

September - October

Starting from

€950

Per person

cover image
avatar image

4.7

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

39 departures available

April - November

Starting from

€1,640

€1,558

Per person - min 2 pax

cover image
avatar image

5.0

Super!

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

One departure available

September

€212

Per person

cover image
avatar image

4.7

Premium

Seychelles by Catamaran: Cabin Cruise with Full Board

Indian Ocean: Seychelles

7 days - 7 nights

37 departures available

January - December

Starting from

€1,760

Per person - min 2 pax

cover image
avatar image

4.7

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

Starting from

€900

Per person

cover image
avatar image

4.7

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

cover image
avatar image

4.7

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

October - November

€1,000

Per person

cover image
avatar image

4.8

Super!

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

Italy: Tuscany

7 days - 7 nights

2 departures available

September

€850

Per person

cover image
avatar image

4.4

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

64 departures available

January - December

Starting from

€1,290

€1,161

Per person - min 2 pax

cover image
avatar image

4.4

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

44 departures available

January - December

Starting from

€1,680

€1,344

Per person - min 2 pax

cover image
avatar image

4.4

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

26 departures available

May - October

Starting from

€1,305

€1,044

Per person - min 2 pax

Why book a holiday with Sailsquare?

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

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

1477 reviews

avatar image

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

09/8/2026

Rosita L.

-

IT

Much more than just a holiday! An unforgettable experience where nothing is left to chance. Everything bordered on perfection, from the itinerary to the food (impeccable raw material and preparation, restaurant-like, if not better!), from the moments on board to those on land. Andrea is an expert navigator and a great connoisseur of the area, you can only trust him and rely on him to spend a dream week. To make everything even more relaxing the constant care of Arianna, the hostess, a discreet presence and attentive to everything, from morning to evening! Also unexpected was the wonderful group of people with whom I was lucky enough to share the experience. In short, expectations were very high and all were abundantly exceeded!

Summer 2026 - Catamaran week in the Pontine Islands

09/8/2026

Elisa B.

-

IT

Very good skipper, experienced and. always available. Also the impeccable hostess service (congratulations Giulia) It and 'a wonderful holiday .. Sea, relaxation and great food! Absolutely recommend
avatar image

DALMATIAN Paradise - Catamaran cruise with hostess FULL BOARD

09/8/2026

Antonio F.

-

IT

Truly amazing crew. Very professional, attentive to the needs of guests and personable.
avatar image

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

09/7/2026

GURMEET S.

-

US

Sailing around Martinique, St Vincent and the Grenadines, was spectacular, with excursions for a small fee highly memorable. The skipper Gerard was extremely professional, skilled, providing a smooth, flawless sail on a 54 foot, high quality, well equipped catamaran with very comfortable cabins. This experience could easily have been a 5 star rating, were it not for the one crew member dedicated to general guest services and cuisine on board. Dream Yacht Charter employed someone lacking the minimum professional skills one would expect in the hospitality sector. The crew member had an indolent, disinterested and shoddy attitude, leaving guests feeling like a cumbersome burden. Simply asking politely for extra utensils or plates at meal times was met with scowls and complaints about extra washing up! The lack of hygiene on board was also unacceptable with whatever dirt that accumulated over the week inside the cabins and common areas building up. The kitchen was only superficially cleaned and on more than one occasion left flies and insects to fester. Cuisine cooked on board was generally flavourless, uninspired and even insufficient on occasion. This was frustrating when the program is full board for the week. We have travelled on other vessels with other companies and had a far better level of service for similar cost. All that said, we had a wonderful week sailing, we just would not book with this company again.

Customer Support

customer support

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!

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

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964