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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!

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

Per person

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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

4 departures available

June - September

Starting from

€1,050

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

21 departures available

January - December

Starting from

€1,250

€1,125

Per person - min 2 pax

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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

Per person

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5.0

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August

Starting from

€1,050

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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4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,160

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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New

Cruise in southern Sardinia: charm and turquoise waters in schooner with hostess and full board

Italy: Southern Sardinia

6 days - 6 nights

11 departures available

July - September

Starting from

€1,200

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

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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

1429 reviews

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Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/24/2026

Isla W.

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CA

My mom and I had an amazing time on board Bledar’s boat! I am celiac and was nervous about eating on board but Bledar was so good at making sure I had a lovely gluten free meal without cross contamination. And above all, the trip was awesome; hiking up volcanos, incredible swimming spots, the delicious food and people we met along the way, we will definitely be back! We already miss all the laughs we had at dinner watching the most beautiful sunsets. And his skipper Alessandro was most helpful and kind, highly recommend!!
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Tuscany and Corsica: sailing sun adventure good food energy and well-being

06/24/2026

Mariacristina M.

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IT

Hello! Despite the postponement of the start date to the 19th for technical reasons, I would say that it could not have gone better! A wonderful experience, definitely to be repeated... Great company, top boat, even better food! I thank and hug Daniele and Mariapia for the passion, kindness and care for the hospitality of their guests, a real pampering! See you next😘 time Fair winds!!

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

06/24/2026

Cristina B.

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IT

My first holiday with the wind, the real one. Constant 22 knots whizzed through the waves. Exciting! Then in the sheltered bays an indescribable turquoise sea awaited us. Top holiday
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Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/23/2026

Kim W.

-

CA

An amazing experience, not simply a choice destination (nature, culture, cuisine, weather) but truly memorable from the standpoint of staffing, communication and service. From the moment you book the trip, Bledar is in contact, verifying your needs. I felt 100% certain my celiac daughter would be well-supported on the journey with an unusual sophistication of dietary understanding. Bledar is an excellent chef for celiacs and non-restricted diets alike. In addition to his captain credentials, he is a delight to talk with and the purveyor of fun. His magnetic personality gives him so many connections to the community that you will be guaranteed to enjoy the best nature, eating, shopping spots. Whatever you desire Bledar and his first mate Alesandro will make the memory possible! I would go back and sail with them in a heartbeat.

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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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