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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!

Weekend in Ogliastra, super Sardinia with skipper and hostess

Italy: Southern Sardinia

3 days - 2 nights

2 departures available

September

€690

€621

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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4.9

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

September

€945

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

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

€1,075

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

7 departures available

July - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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1.0

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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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure - cook on board

Italy: Tuscany

6 days - 6 nights

3 departures available

July - August

Starting from

€950

Per person

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4.9

Egadi Islands by catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - September

Starting from

€1,100

Per person

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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

1470 reviews

Maddalena Archipelago, southern Corsica: wonderful Sardinia

07/20/2026

Dario P.

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IT

Boat not new, but functional and well divided and equipped. Obviously a top destination, between Northern Sardinia and Corsica. Skipper and hostess (brother and sister) kind, but... each smoked 20+ cigarettes a day and there were always full ashtray glasses and there was always the smell of smoke, almost everywhere. I understand that there is freedom to smoke, but a little attention to those who do not smoke would be expected. In addition, great disorder in the dinette, with provisions not stored but left ... under the table, and fires and sink almost perpetually dirty from the previous meal... Honestly, having also had other experiences, and considering the costs, I expected more attention. Good food and well prepared.

Tuscany and Corsica: sailing sun adventure good food energy and well-being

07/20/2026

Stefano M.

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IT

The July 2026 experience with my 25 and 12 year old children went above and beyond our expectations. We all had a great time thanks to the fantastic couple of skippers and the great company of the other travelers. Although not modern, the boat is sufficiently large and in excellent condition. Among the destinations we appreciated Capraia and Corsica more than Elba. The skipper Daniele is prepared and nice, he cheered us up with countless and funny anecdotes, while Mariapia always put us at ease and prepared light dishes appreciated by all. Time dilated, the three days seemed much longer, leaving us with the desire to repeat the experience as soon as possible. Again a special thanks to Daniele and Mariapia, we really couldn't find better. See you soon!!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/20/2026

Andrea C.

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IT

Andrea is very organized and precise. Perfect I would say for a holiday with friends

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

07/20/2026

Katia M.

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FR

Thank you to Alessandro and Carlo for a wonderful week. Tutto benissimo. It was also very pleasant to sail not far from his brother Andrea. Very good atmosphere. To be done again.

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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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