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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

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

12 departures available

June - October

Starting from

€1,525

Per person - min 2 pax

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5.0

Moments that last a lifetime - In Croatia from Rimini - All inclusive

Croatia: Split Archipelago

8 days - 8 nights

One departure available

July

€1,080

Per person

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4.4

Enjoy the Aeolian Islands with skipper and hostess

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

August - September

Starting from

€1,039

Per person

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4.4

Premium

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

Caribbean: Grenadines & Martinique

9 days - 10 nights

17 departures available

June - December

Starting from

€1,680

€1,260

Per person - min 2 pax

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

7 departures available

June - October

Starting from

€845

€761

Per person - min 2 pax

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5.0

Yoga, meditation and healthy eating in a natural paradise

Caribbean: San Blas Islands - Panama

5 days - 5 nights

5 departures available

June - August

€1,600

Per person

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4.9

Quattro giorni all'Elba - Hostess a bordo

Italy: Tuscany

4 days - 5 nights

2 departures available

July - August

€750

Per person

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4.3

Sailing adventure in the sea of Ulysses - Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

5 departures available

July - August

Starting from

€750

€675

Per person

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4.6

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

Malta: Malta

6 days - 6 nights

10 departures available

August - October

Starting from

€690

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure - cook on board

Italy: Tuscany

6 days - 6 nights

4 departures available

July - August

Starting from

€850

Per person

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

Italy: Sicily

3 days - 2 nights

8 departures available

July - September

Starting from

€315

€284

Per person

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5.0

An all-inclusive day on a sailing boat

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

€180

Per person

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.

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

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

1425 reviews

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

06/22/2026

Elisabetta M.

Breathtaking experience, fantastic landscapes and I had the pleasure of sharing all this with special people! A special thanks to Alessandro and Carlo for their availability and professionalism! A must do.
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

06/22/2026

Alessandro A.

-

IT

Wonderful holiday both for the itinerary and for the skipper, Riccardo is an exquisite person, competent and very helpful (excellent management of the galley and, above all, excellent cook). The boat requires an "important" commitment during sailing journeys but, for my conception, it is the beauty of this type of experience.

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

06/22/2026

Chiara A.

-

IT

Beautiful places and the skipper, a great navigator and an excellent host

North Sardinia and Corsica: blue seen from a sailboat

06/22/2026

Sailor

Experience to try if you want a week of peace and sharing.

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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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