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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!

Sail in Mallorca! - Cook on board

Spain: The Balearic Islands

5 days - 5 nights

One departure available

June

€850

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

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5.0

Super!

Aeolian Islands and Egadi Islands in a week with chef on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

July

€800

Per person

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4.8

Super!

From Palermo to Marsala: magical week on a catamaran with hostess

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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5.0

Super!

Sailing from Menorca to Sardinia

Spain: The Balearic Islands

5 days - 5 nights

One departure available

June

€700

€630

Per person

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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

20 departures available

June - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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5.0

Super!

Sailing adventures: summer sailing camps IN ENGLISH - for children from 9 to 14 years old

Italy: Tuscany

5 days - 5 nights

2 departures available

June - July

€660

Per person

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4.8

Super!

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

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

5 departures available

July - October

Starting from

€779

€701

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

3 departures available

June - October

Starting from

€950

€760

Per person

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4.8

Super!

Catamaran with Chef in the magical sea of the Ionian Islands - Holiday for SINGLES

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,450

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

Per person

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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

1408 reviews

Long weekend of June 2nd on the Costa Smeralda

06/4/2026

Silvia B.

-

IT

Francesco guided us in the world of relaxation and zero stress, lulled by the sea, following the rhythm of the sun and the delicious dinners prepared by him, transmitting his love for sailing and for [hidden]. Removed the watch and forgotten the cell phone, the only commitments are swimming, balancing on. Sup, prepare loaded spritzes and exchange jokes and life anecdotes with those who become your roommates (in this case excellent) for a few days. Thank you Francesco and thank you crew!

Long weekend of June 2nd on the Costa Smeralda

06/4/2026

Zuzana P.

-

BE

Top of top! Francesco clearly knows and loves his craft - we all had a very good time with him on board his super [hidden] who gave us unforgettable moments. Absolutely to be redone!
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Long weekend of June 2nd on the Costa Smeralda

06/3/2026

Francesca B.

-

IT

Great experience. Francesco is very professional and helpful. Great cook. 5 star service!

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

05/18/2026

David B.

-

MQ

Amazing week in the Grenadines. Great group for the boat. A big thank you to the Skipper, Will and the hostess Maîka who prepared delicious meals for us. It was a perfect week for me. I recommend.

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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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