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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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4.4

Premium

BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

47 departures available

January - December

Starting from

€1,415

€1,274

Per person - min 2 pax

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5.0

3 days sailing among the hidden gems of Palermo - All inclusive & flexible dates

Italy: Sicily

3 days - 2 nights

5 departures available

September - October

Starting from

€315

€284

Per person

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4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

25 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

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4.4

Premium

ANDAMAN Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

10 days - 10 nights

17 departures available

January - December

Starting from

€2,960

€2,664

Per person - min 2 pax

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New

Premium

All inclusive catamaran cruise on Excess 11 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,875

Per person

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New

Exclusive night on a sailing boat with private excursion in Tenerife

Atlantic islands: Canary Islands

1 day - 1 night

19 departures available

September - October

€125

Per person

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New

Gulf of Poets: Shared Sunset Tour by Catamaran

Italy: Liguria

1 day - 0 nights

37 departures available

September - October

Starting from

€120

Per person

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4.4

Premium

PRASLIN Paradise - Catamaran cruise with hostess FULL BOARD

Indian Ocean: Seychelles

7 days - 7 nights

65 departures available

January - December

Starting from

€1,970

€1,773

Per person - min 2 pax

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas with the solar eclipse

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

July - August

Starting from

€1,299

€1,169

Per person

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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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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

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

1656 reviews

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/22/2026

Marcella L.

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IT

I spent a wonderful week on board the catamaran discovering the Aeolian Islands together with a group of great people! It was the perfect choice to experience this archipelago to the fullest. Every day a different emotion and spectacular bays in which to wake up. A special thanks to Fabrizio, who with great professionalism and sympathy guided us to the best moorings, always anticipating the weather and to Monica the Super Hostess who pampered us throughout the week with her desserts and excellent cuisine. 100% recommended holiday

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

09/22/2026

Birgit H.

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DE

What a great trip! Seen a lot! Ate a lot! Beautiful coves where you can anchor and admire the sunset with an aperitivo. Bledar is a very responsible skipper, very helpful and always attentive to the wishes of his guests. He makes several suggestions every day and knows the most beautiful corners. And his cooking skills are excellent too! It's just a pity that there was too little wind to sail!

Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/21/2026

Pierluigi O.

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IT

Spectacular catamaran. Well structured itinerary. A truly unforgettable experience in the Aeolian Islands! The catamaran was the perfect way to experience the sea, but what really made the difference was the professionalism and passion of the skipper and cook on board. Angelo, the skipper, proved to be a true sea dog: a great connoisseur of the islands, always attentive to the conditions of the sea and the needs of all of us. He took us to wonderful bays and coves, making us discover spectacular corners and making every navigation pleasant and safe. His experience and tranquility allowed us to enjoy every moment without worries. And then the cook, Diego, a real surprise! Every day he delighted us with delicious dishes, well-kept and rich in flavors, enhancing the specialties and products of the territory. Eating on board, with the Aeolian sea in front of our eyes, was one of the best moments of the holiday. A professional couple who, with competence, availability and sympathy, made the trip even more special. An experience that I absolutely recommend and that I would do again without hesitation!
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Egadi Islands by catamaran

09/21/2026

Marco C.

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IT

From 12 to 19 September a memorable week. Giuseppe (the skipper) excellent travel companion, experienced and professional. As he says... TOP! He is a great connoisseur of the Egadi Islands and shrewd in every detail. He makes you feel at home in his catamaran that he loves and shares with passion. What can I say, certainly to be repeated.

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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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