header cover
sailsquare logo

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

4.9

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

September - October

€950

Per person

cover image
avatar image

4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

September - October

Starting from

€1,800

Per person

cover image
avatar image

4.3

Premium

GRENADINES 11 days on a ALL INCLUSIVE catamaran with hostess/cook

Caribbean: Grenadines & Martinique

9 days - 10 nights

45 departures available

January - December

Starting from

€1,680

€1,512

Per person - min 2 pax

cover image
avatar image

4.3

Premium

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

Caribbean: Grenadines & Martinique

6 days - 7 nights

65 departures available

January - December

Starting from

€1,250

€1,125

Per person

cover image
avatar image

4.9

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€1,450

€943

Per person

cover image
avatar image

4.3

Premium

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

Indian Ocean: Seychelles

7 days - 7 nights

64 departures available

January - December

Starting from

€1,760

€1,584

Per person

cover image
avatar image

4.9

Under the Caribbean Sun

Caribbean: Antigua and Barbuda

8 days - 9 nights

One departure available

December - January

€2,200

€2,000

Per person

cover image
avatar image

4.9

Under the Caribbean sun on a catamaran

Caribbean: Grenadines & Martinique

8 days - 9 nights

4 departures available

January - March

€1,750

Per person

cover image
avatar image

4.9

Aeolian Islands - Large and new catamaran equipped with every comfort

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€1,030

€927

Per person

cover image
avatar image

4.3

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE

Caribbean: Saint Martin

6 days - 7 nights

51 departures available

January - December

Starting from

€1,125

€1,013

Per person

cover image
avatar image

4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

Starting from

€1,260

Per person - min 2 pax

cover image
avatar image

4.5

Paradise Seychelles by sailing catamaran

Indian Ocean: Seychelles

7 days - 7 nights

2 departures available

November - December

€1,450

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

1208 reviews

avatar placeholder

From Kos to Rhodes on my catamaran

09/13/2025

Danielle O.

-

Germany

Our first tour. We therefore have no comparison options yet and give a benevolent 4 stars. I would have liked better communication, more involvement and more sailing.
avatar image

3 days in Sardinia - Costa Smeralda or AMP Tavolara

09/12/2025

Kim L.

-

United Kingdom

Great trip - highly recommend! We booked for 3 nights/4 days and were on the boat with Renato and another wonderful Italian couple. We had a lovely time! Renato took us to beautiful islands and coves and when the weather was bad we avoided windier areas and he ensured we were always safe. Luckily we had much more good weather than bad! I was a little nervous before the trip because information was a bit limited but Renato is a pro and he has everything taken care of when you arrive- he’s very communicative by WhatsApp once you book. We dropped our bags and then all went grocery shopping for food for the week. We decided the menu together and then Renato handled the cooking (and the cleaning!). We also rented our towels and linens from him and the only extra cost we incurred was gas. Over the 4 days we saw many beautiful places, snorkeld and did stand-up paddle board which he has on the boat. The boat is a beautiful catamaran which Renato owns and takes meticulous care of! We had our own comfortable room and private toilet. You can shower in the little bath but typically you just use the outdoor shower, after you swim. Renato was a great skipper, he had a lot of information for us about the island and ensured we had a good time. He even brought out his guitar at night and we did singalongs to the Beatles and played cards. He has a previous review from a group that had a bad experience but we didn’t experience anything like that and the trip exceeded all expectations. We would definitely like to come again, and next time bring more of our friends! Thank you, Renato! We will always remember this trip!
avatar placeholder

Magnificent week on catamaran between Corsica and Capraia with Hostess

09/11/2025

Valentina R.

-

Italy

We had the pleasure of traveling with skipper Umbo and the experience was truly excellent. A kind, helpful person who is always attentive to the needs of guests. The boat is very beautiful, with attention to detail and kept in perfect condition, immediately transmitting safety and comfort. The trip between Tuscany and Corsica was wonderful, enriched by the professionalism and hospitality of Umbo, who made the experience a real relaxation. Thanks also to the hostess Daniela, who prepared excellent dishes for us and was an exquisite presence on board. Thanks guys, we hope to see you again soon. Highly recommended experience.
avatar image

Different Flotilla: Party and new friends in the Aeolian Islands

09/11/2025

Eleonora N.

-

United Kingdom

It's not the first holiday with Different Sailing, and it never disappoints! Mix of fun and relaxation! Everything organized great, as always! Super recommended holiday!

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

MastercardVisaGoogle PayApple Pay

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