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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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New

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All inclusive catamaran cruise on a Bali 4.2 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€2,060

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

One departure available

October

€1,100

Per person

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4.4

Premium

DALMATIAN Paradise - Catamaran cruise with hostess FULL BOARD

Croatia: Split Archipelago

7 days - 7 nights

22 departures available

May - October

Starting from

€1,315

€1,184

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

6 departures available

September - November

Starting from

€723

€650

Per person

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4.7

Tenerife and La Gomera aboard an 18 m ketch

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

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4.2

Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

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4.4

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

40 departures available

January - December

Starting from

€1,430

€1,144

Per person - min 2 pax

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4.4

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

77 departures available

January - December

Starting from

€1,535

€1,228

Per person - min 2 pax

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4.4

Premium

RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

27 departures available

January - December

Starting from

€2,330

€1,864

Per person - min 2 pax

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

2 departures available

October

€690

Per person

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4.2

Where the blue feels like home: the Ionian islands - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

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4.4

Premium

BORA BORA PARADISE - Mini catamaran cruise with hostess and full board

Pacific Ocean: French Polynesia

4 days - 4 nights

One departure available

October

Starting from

€2,305

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.

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.

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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

1667 reviews

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

09/27/2026

Marino G.

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IT

Thank you Alessandro! You gave us a wonderful holiday. Wonderful bays with emerald water. Every night different places, one more beautiful than the other. Food recommendations and reservations in restaurants. You have always been very helpful and so kind. You have a beautiful boat, but above all very comfortable and clean. Inflatable boat for getting around is luxury! I would also like to thank hostess Carlo. Very nice, kind and always available. Good cook and also fisherman, spoiling us with lunch of freshly caught fish. It was too good! Can't wait to go back!!!

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

09/27/2026

Otto A. B.

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DE

Fantastic trip Top team on board Food 1x Michelin star - THANK YOU Mauro Skipper - fantastic only to recommend Boot Top - Clean nothing to be desired

Fast Sailing Experience between Authentic Islands and Good Food

09/27/2026

Janine E.

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CH

The sailing week was a unique experience. Annalisa & Lorenzo have a lot of experience & we have always felt comfortable. Everything was very well organized & the food was really delicious! Most of the time we spent the night in lonely bays. Thank you very much for these great memories.
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Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

09/27/2026

Giuseppe P.

-

IT

Wonderful holiday, the skipper Alessandro and the hostess / chef Helena were perfect!

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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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