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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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4.8

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

August - October

Starting from

€900

Per person

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4.4

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

69 departures available

January - December

Starting from

€1,250

€1,125

Per person - min 2 pax

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5.0

Wellness, sun, sea and adventure: a weekend full of sailing!

Italy: Tuscany

3 days - 2 nights

2 departures available

September

€230

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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5.0

Super!

Sail in Sardinia! - Cook on board

Italy: Northern Sardinia

5 days - 5 nights

One departure available

July

€1,000

€900

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

2 departures available

October

€950

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,090

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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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

8 departures available

July - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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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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4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€1,000

Per person

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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

10 departures available

July - October

Starting from

€1,305

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

1454 reviews

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All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

07/12/2026

Axel G.

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DE

We enjoyed the sailing trip very much, the skipper was extremely nice, helpful and courteous. We were able to see a lot, and capture the typical of the islands and the Amalfi Coast. We also had a very nice family of sailors on board. Only the wet room could have worked and smelled a little better. What we didn't really realize, however, was that everything inclusive did not refer to the food on board, but obviously only to the sightseeing destinations. This is misleading and should be better formulated in future offers!

Conquering the Aeolian Islands - Cook on board

07/12/2026

Francesca V.

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IT

Wonderful experience!! Sergio and Carmen are wonderful 'boat' hosts... They support you and make you feel comfortable at all times!! Beautiful tour in the Aeolian Islands (6 out of 7 as scheduled!!) that can be enjoyed from the sea and also visited partly by land!! The company was great and this made the week even more enjoyable!! The only flaw .... you come back with a few extra kilos due to the excellent cuisine of Sergio who is not only a true connoisseur of the sea and navigation but also an excellent cook! I highly recommend this experience with two amazing people who will make you live every day to the fullest!!

Yoga, meditation and healthy eating in a natural paradise

07/10/2026

Uwe D.

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CH

There are not enough words to describe how grateful I am for this experience with [hidden] Sailing. From the first moment, I felt so much love, warmth, and kindness. It was more than a sailing trip—it felt like coming home to beautiful people with beautiful hearts. Yoga and meditation opened a completely new world for me. They gave me peace, strength, and moments I will never forget. Free diving taught me that true strength comes from a calm mind. It showed me the powerful connection between mental focus and body control, and it changed the way I see myself. Every meal was healthy, fresh, and prepared with so much love and care. You could feel the heart behind everything they did. Thank you for sharing your passion, your knowledge, and your beautiful energy. I leave with unforgettable memories, a full heart, and a different view of life. If you are looking for more than just a vacation, this is the place. It is a life-changing experience that will stay in your heart forever. Thank you, Paola, Kyndera and Luca. I will come back…
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Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

07/9/2026

Emanuela C.

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IT

Super positive experience, fantastic catamaran and super professional cabin crew. Silvia, the chef, was a wonderful girl, welcoming the needs of all customers and working impeccably.

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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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