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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!

Ibiza & Formentera All inclusive week with Cook

Spain: The Balearic Islands

6 days - 6 nights

5 departures available

July - September

Starting from

€650

€585

Per person

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€935

€748

Per person

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4.9

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€550

Per person

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4.8

Super!

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€1,080

€918

Per person - min 2 pax

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4.8

Super!

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

One departure available

July - August

€679

€543

Per person

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5.0

Super!

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

Malta: Malta

6 days - 6 nights

6 departures available

August - September

Starting from

€740

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

One departure available

August

€2,947

€2,800

Per person

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4.8

Super!

Egadi Islands by catamaran with stewardess and cook on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

July

€1,350

€1,215

Per person

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4.7

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

9 departures available

August - November

Starting from

€1,455

€1,382

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

Per person

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5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€1,300

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

1192 reviews

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

07/17/2025

Lucilla C.

-

United Kingdom

A 5 star experience! Went with my partner and two friends, we were very lucky at clicking so well with the other two passengers and by the end of the week we had so much fun we decided to stay in touch. The places we visited were breathtaking, our skipper Alessandro was the warmest ever, he took good care of us and was always making sure we were comfortable. Five stars also to Carlo who was prepping us delicious food and making sure we didn't move a finger and enjoyed the holiday (despite our attempts to help!). They have SUPs that we were able to use, masks for snorkeling, we went looking for sea urchins and we saw plenty of fish (even barracudas!). The moments we went only with the sail and no enigne were magical. We will definitely do it again!
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Ibiza & Formentera All inclusive week with Cook

07/17/2025

Silvia C.

Spending a holiday aboard with Alex and Mausi was nothing short of magical. From the very first moment, the atmosphere on the boat was calm, joyful, and full of positive energy. Alex was an outstanding skipper—professional, friendly, and always ready to help with a smile. His easygoing nature and deep knowledge of the sea made every moment enjoyable and relaxing. And then there was Mausi—Alex’s wonderful mother and our incredibly talented chef. Her meals were delicious, prepared with love and creativity, turning every lunch and dinner into a cozy celebration. You could truly taste the warmth of home in every bite. This sailing experience wasn’t just a vacation, it was a beautiful journey shared with genuinely kind people who made us feel welcome and cared for every single day. Highly recommended for anyone seeking authentic moments, stunning views, and unforgettable company!
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Tre giorni a vela tra La Maddalena e Costa Smeralda

07/16/2025

Andrea C.

-

Italy

Wonderful experience with skippers Enrico and Daniela. We met a passionate couple, a lover of the sea, who gave us a splendid cruise, sharing their passion with us. The boat [hidden] is small but super-cozy, it was our houseboat for 3 days. The only regret was the landing, we would have liked to stay longer!
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2025

Alberto M.

-

Italy

Riccardo proved to be an excellent Skipper, a true professional, always ready to take advantage of any gust of wind to unfurl the sails. Great cook and great company. A boat experience with Riccardo is highly recommended.

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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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