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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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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Karpathos

Greece: Dodecanese

7 days - 6 nights

One departure available

September - October

€950

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.8

Super!

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Italy: Naples & Amalfi Coast

3 days - 2 nights

27 departures available

July - October

Starting from

€1,325

Per person

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4.8

Super!

Capri and Amalfi Coast by CATAMARAN BALI 4.3 ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

July - October

Starting from

€1,800

Per person

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4.9

Super!

Corfu - Lefkada ONE WAY: an exclusive adventure with hostess on board

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€464

Per person

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4.7

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

10 departures available

July - October

Starting from

€1,100

€1,045

Per person

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4.3

Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

Italy: Tuscany

5 days - 6 nights

9 departures available

July - September

Starting from

€900

Per person

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

Croatia: Split Archipelago

7 days - 7 nights

10 departures available

July - September

Starting from

€1,100

Per person

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4.8

Lampedusa, Lampione e Linosa fra colori magici

Italy: Pantelleria and Lampedusa

7 days - 7 nights

One departure available

July - August

€679

€577

Per person

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Discovering the Aeolian Islands by catamaran with hostess

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August - September

€1,250

Per person

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4.3

Premium

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

Indian Ocean: Seychelles

7 days - 7 nights

73 departures available

January - December

Starting from

€1,760

€1,584

Per person

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4.4

Enjoy the Aeolian Islands with skipper and hostess

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

July - September

Starting from

€930

Per person

Why book a holiday with Sailsquare?

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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 - Sailing or catamaran cruises with hostess or onboard cooking service

1169 reviews

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Aeolian Islands - A week on a sailing boat with skipper and assistant

07/1/2025

Rodolfo B.

-

Italy

Vacanza praticamente perfetta, a partire dalla descrizione, dall'organizzazione, dalle informazioni dettagliate fornite prima della partenza. Anche grazie al meteo favorevole e agli ottimi compagni di viaggio, abbiamo esplorato tutte le Eolie dedicando il giusto tempo a tutto, anche a noi stessi, senza correre. Non solo, con le escursioni via terra l'esperienza è andata ben oltre le mie aspettative. Luigi ed Enrico sono persone squisite, disponibilissime, con cui è molto piacevole conversare su ogni argomento, costantemente impegnate a fare in modo che tutto proceda per il meglio. Al rientro saluto tutti con un nodo alla gola, sperando di ritrovarsi in futuro magari ancora in barca.
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Weekend on the French Riviera from Imperia - Stewardess on board

07/1/2025

Giorgia T.

-

Italy

Vittorio e Giulia sono stati molto accoglienti e flessibili nel gestire le varie richieste. Due giorni meravigliosi!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/30/2025

Gilberto B.

-

Italy

Alessandro, Carlo, Andrea e Marta sono andati oltre ogni possibile aspettativa regalandoci una settimane di relax, incantevoli spot nello ionico, deliziosi pranzi a bordo e fuori. Abbiamo trovato disponibilità, sensibilità e accoglienza fuori dal comune. Barca pulita, ottima comunicazione e organizzazione. Nessun dettaglio lasciato al caso, una vacanza indimenticabile!
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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

06/30/2025

Beatrice S.

-

Spain

No se podía esperar más de un viaje. El catamarán grande y nuevo. A/C siempre que hacía falta y agua en abundancia. El Capitán Lutius no podía ser más profesional y simpático. Nos hizo sentir a todos cómodos y siempre proponiendo hacer diferentes actividades en un ambiente divertido y desenfadado. Karin, la chef igualmente agradable y divertida. Muy profesional y atenta a nuestras necesidades. Los lugares que visitamos de ensueño y a pesar de algunas lluvias en línea general ha merecido la pena navegar fuera de temporada al estar prácticamente solos en los sitios más alucinantes. Siempre hemos tenido suerte con el resto de los clientes y en este caso no ha sido diferente y a pesar de ser mayoritariamente de habla francesa nos hemos comunicado muy bien en inglés.

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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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