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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

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

5 days - 6 nights

One departure available

September

€1,995

Per person

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A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

7 departures available

September - November

Starting from

€1,350

Per person

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4.3

Premium

BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

49 departures available

January - December

Starting from

€1,250

€1,125

Per person

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4.3

Premium

ANDAMAN Dream Premium - Catamaran Cruise with Hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

10 days - 10 nights

15 departures available

January - December

Starting from

€2,660

€2,394

Per person - min 2 pax

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4.3

Premium

Dubrovnik & Split Discovery Cruise - Hostess & Half Board

Croatia: Split Archipelago

7 days - 7 nights

2 departures available

September - October

Starting from

€835

Per person - min 2 pax

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4.1

East Coast of Sicily From Taormina to Portopalo. Cook on board

Italy: Sicily

6 days - 7 nights

6 departures available

October - December

€625

Per person

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Explore San Blas paradise

Caribbean: San Blas Islands - Panama

4 days - 4 nights

One departure available

September

€200

Per person

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5.0

Two days on a sailing boat in Elba: zero stress!

Italy: Tuscany

3 days - 2 nights

2 departures available

September

€300

€270

Per person

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4.3

Premium

CORSICA NORD Dream - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

10 departures available

June - October

Starting from

€1,405

Per person - min 2 pax

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

1345 reviews

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

09/14/2025

Madison T.

-

Canada

Wow wow wow. We had no idea what to expect when booking this trip, it exceeded every expectation. Alessandro is knowledgeable and kind, his passion for what he does shows. Carlo is sunshine in human form, the food he makes on board is incredible. Eros is the perfect addition to the boat. We felt so well taken care of the entire time. The weather was perfect early September with it being less hot than July/aug. The rooms in the boat are comfortable but it does get hot down there to sleep, I could see a usb fan being useful for sleeping. Do not hesitate to book this trip with sailing sunset.
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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/14/2025

Anna Maria C.

-

Italy

Overall positive experience.
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Aeolian Islands by catamaran, professional skipper/hostess, what else?

09/14/2025

Alessandro M.

-

Italy

This is not a review but an invitation to participate in this fantastic adventure. Fabrizio is an incredible person and skipper, he knows every rock, anchorage and current of the Aeolian Islands and then cooks divinely. Arianna will pamper you, keeping the boat always clean and tidy. you will only have to think about which costume to wear! If you are lucky, like me, to find wonderful travel companions, it will be an unforgettable experience. 5 hearts, not stars!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/14/2025

Maude A.

-

Canada

Wonderful week with Alessandro and Carlo! We ate well and saw beautiful places. Carlo is an angel, always ready to help. Alessandro is an extraordinary skipper. He knows how to make us feel confident and safe. He too is always ready to help. The boat is beautiful. The activities were fun and the pace of the activities was good. We were also happy to be able to sail when the wind allowed. We also had a great week with the new people we met on the boat. I 100% recommend this cruise!

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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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