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Sailing or catamaran cruises with hostess or onboard cooking service

Embark on a vacation where you won’t have to worry about cooking and can fully enjoy the sea without a care. Choose a cruise with a hostess if you want a professional and comprehensive service, from cooking and cleaning to tidying up. If you only want to avoid cooking, select a vacation with cooking service: other tasks, such as setting the table or washing the dishes, will be managed in collaboration with other guests onboard.

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4.8

Super!

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Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€1,300

Per person

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4.8

Super!

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Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

4 departures available

October

Starting from

€2,250

Per person

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4.7

Premium

Seychelles by Catamaran: Cabin Cruise with Full Board

Indian Ocean: Seychelles

7 days - 7 nights

33 departures available

January - December

Starting from

€1,760

Per person - min 2 pax

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

3 departures available

October

€570

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

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5.0

Super!

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

October

€275

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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5.0

Super!

Squid Festival in Capraia with a professional skipper and chef

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

Per person

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4.4

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

64 departures available

January - December

Starting from

€1,440

€1,152

Per person - min 2 pax

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4.4

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

Caribbean: Grenadines & Martinique

9 days - 10 nights

43 departures available

January - December

Starting from

€1,840

€1,472

Per person - min 2 pax

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4.4

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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?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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Reviews - Sailing or catamaran cruises with hostess or onboard cooking service

1676 reviews

Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/29/2026

Mark M.

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GB

We had a brilliant week sailing with Alessandro and Carlo! Alessandro is a very knowledgeable skipper, with brilliant recommendations and excellent choices of destination. Even though our schedule was disrupted by the weather we had a great time sailing round the islands and he provided us with excellent food recommendations each evening. The hospitality on the boat was great, as was Carlo's cooking and I can't recommend the experience enough. Thank you again

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

09/29/2026

Sergio V.

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IT

Alessandro is first of all a great person, then as far as the week is concerned he proved to be available and attentive to the requests and desires of the crew, precious for suggestions and advice on what to do. He always accompanied us even on the ground. Helena, passionate about her work, has always prepared different dishes that are satisfying for the taste and for the eyes. It couldn't have been better than this!

Sailing paradise in Greece on a big 50 ft boat: the best local experience

09/29/2026

Sailor

Excellent experience, clean and efficient boat. excellent, cuisine, top quality food, nice company, owner and staff, they do this job with feeling and dedication, Too bad we didn't get to Hydra., even if it was optional, skipper prepared but a little too plastered in his role. however, experience to be redone with this team, perhaps improving my English and with a new itinerary.

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/29/2026

Gloris M.

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IT

We had a wonderful week. The skipper Fabrizio, always very kind, made us feel safe with great professionalism and tried to satisfy all our requests compatibly with the weather. The hostess Monica, always discreet and patient, knew how to take care of the guests without being intrusive. He prepared tasty dishes that helped make the holiday even more enjoyable. If we could we would leave immediately for another holiday with this crew!

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Why choose a sailing vacation with hostess or crew

  • Do you want to enjoy an all-round relaxing vacation, without having to think about anything? On board these vacations you will find a crew who will brighten up your stay.
  • Find the perfect vacation for you: choose a vacation with a hostess who will take care of the all-round service or choose a vacation with an on-board chef who will prepare the best local dishes for the guests.
  • Enjoy the vacation you've been dreaming of for a long time after a year of work: devote your time only to having fun and relaxing, without having to lift a finger.
  • Are you planning your vacation with children and don't want to have any thoughts other than enjoying time with your family? A vacation on a boat with a crew is ideal!

The best destinations for a sailing vacation with crew

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Sailing vacations with hostess or crew in the Mediterranean: discover the wonders of our sea, following the advice of the skipper, perhaps sipping a cocktail prepared by the staff on board. You'll be spoiled for choice for a cruise on a sailing boat or catamaran or gulet with family, friends or new people met on board. Marinas and marinas, historic and lively villages, islands full of small restaurants or almost deserted islands, waters from green to turquoise, wide beaches and hidden coves: a boating vacation in the Mediterranean offers everything!

In Italy the best destinations are the Tuscany from whose coast to reach the island of Elba and the Giglio but also the Corsica. The Northern Sardinia, trendy and exclusive, but also the wild Southern Sardinia, or the Aeolian Islands, the Egadi Islands, the Pontine Islands and the Amalfitan Coast.

Do you prefer to go abroad? Choose a sailing vacation with hostess or crew in Croatia or in Greece, choosing a custom itinerary among the dozens and dozens of islands. But that's not all: Côte d'Azur, Corsica, Balearic Islands are all fantastic experiences, surpassed perhaps only by a vacation aboard a gulet in Turkey with crew for maximum comfort!

Hosted or crewed sailing vacations in the Caribbean: sailing on a catamaran in the Caribbean is the best way to enjoy the winter sea in Martinica, Grenadines, Cuba, Antigua and Barbuda, British Virgin Islands, Guadeloupe: excellent sailing conditions and a unique atmosphere characterize each island of the archipelago. Whether by catamaran or by sailboat, in the Caribbean your skipper will take you to explore small deserted bays even in high season, so that your cruise will be a unique and unforgettable experience.

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