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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!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€793

€714

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

12 departures available

June - October

Starting from

€550

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

5 departures available

June - September

Starting from

€935

€748

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

12 departures available

June - October

Starting from

€550

Per person

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5.0

Super!

Ibiza & Formentera All inclusive week with Cook

Spain: The Balearic Islands

6 days - 6 nights

11 departures available

June - September

Starting from

€650

€585

Per person

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4.6

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

9 departures available

June - November

Starting from

€1,455

€1,382

Per person

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4.8

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

June - August

Starting from

€2,062

€1,340

Per person

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5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

4 departures available

July - August

Starting from

€1,100

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

June - August

Starting from

€1,115

€1,059

Per person

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5.0

Super!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

July

€790

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

2 departures available

August

Starting from

€2,737

€2,600

Per person

Why book a holiday with Sailsquare?

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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

1142 reviews

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

06/14/2025

Linda H.

-

Australia

It was an amazing experience exceeded my expectations. The all female crew were excellent They went over and above their duties. They were very caring respectful and tried to make our experience a positive enjoyable experience which they did perfectly. It was one of the best Sailing trips I have ever done.
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Dalmatian Dream - week on catamaran ALL INCLUSIVE with hostess/cook

06/12/2025

Altamir T.

-

Brazil

The experience of the Dalmatian Dream cruise, from May 24th to 31st, was not entirely satisfactory. Despite all the efforts of Captain Marino and the cook Mila, the program was interrupted several times for repairs to the boat. As a result of these problems, comfort and well-being were also impaired. Despite these problems, it is worth noting that the food was excellent and that the general conditions of the cabin were good. Additionally, the reception service at the office was kind and attentive, providing support and guidance in my specific case for a health problem
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

06/11/2025

Gemma M.

-

Italy

Un soggiorno meraviglioso reso speciale da Andrea e Marta, due persone splendide che ci hanno fatti sentire subito a casa. La barca è bellissima, curata e in perfette condizioni. Andrea, skipper esperto e sempre disponibile, ci ha accompagnati con il gommone alla scoperta dei luoghi più belli e nascosti, lasciandoci sempre liberi di scegliere il ritmo della giornata. Marta, cuoca eccezionale, ha preparato piatti deliziosi e ha mantenuto la barca sempre pulita e in ordine con una discrezione e una dedizione davvero ammirabili. La compagnia di Matthias, cane dolce e affettuoso, è stata un piacevole valore aggiunto. Un’esperienza davvero unica.
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Magical weekend in Palmarola and Ponza

06/10/2025

Katia C.

-

Italy

Piacevolissima vacanza in compagnia di Federico e Costanza. La Compagnia e la barca hanno reso tutto indimenticabile.

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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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