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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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4.9

Mykonos to Kos: Epic Sail with Stewardess on Board

Greece: Cyclades

6 days - 7 nights

One departure available

June

€750

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

12 departures available

January - May

Starting from

€1,500

€1,350

Per person

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Escape to the Ionian Blue - Corfu

Greece: Ionian Islands

6 days - 6 nights

29 departures available

March - October

Starting from

€850

€765

Per person

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4.3

Premium

BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

38 departures available

January - December

Starting from

€1,250

€1,125

Per person - min 2 pax

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4.9

Full sail in the blue of Ionian Greece with hostess on board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€810

Per person

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4.9

From Kalamata to Lefkada: from the Peloponnese to the Ionian Sea with Hostess on Board

Greece: Peloponnese

6 days - 7 nights

One departure available

August

€1,100

Per person

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4.3

In the Sea of Ulysses among the most beautiful islands on Bavaria 50 with hostess

Greece: Ionian Islands

6 days - 7 nights

8 departures available

July - August

Starting from

€750

€638

Per person

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4.8

The paradise of the Seychelles by Catamaran with Hostess

Indian Ocean: Seychelles

7 days - 7 nights

One departure available

March - April

€1,350

Per person

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4.3

Premium

ANDAMAN Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

10 days - 10 nights

11 departures available

January - December

Starting from

€2,700

€2,430

Per person - min 2 pax

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4.8

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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4.3

Premium

Dubrovnik & Split Discovery Cruise - Hostess & Half Board

Croatia: Split Archipelago

7 days - 7 nights

18 departures available

May - October

Starting from

€915

€824

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

8 departures available

April - May

€650

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

1379 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/11/2026

Elena Maria F.

-

Italy

The experience was wonderful. There were 2 inconveniences, the first was the wait in the port of departure of two guests who instead of arriving at 18.00 arrived at midnight and this led to a change of program on the first day, in fact we did not visit Bequia with Port Elizabeth at all. The second note is on the cook, who said she was at her first experience in that role and in the kitchen, in fact the management of the galley was bad. The dishes were too elaborate and used too many ingredients to the detriment of the quantities. After the middle of the week he realized that he could cook simpler and more abundant things. For the rest it was a wonderful experience.
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GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

10/28/2025

Anne-Marie G.

-

Curaçao

Amazing experience
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North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine

10/25/2025

Teresa B.

-

Germany

We were very lucky to spend 7 days with Bledar on his sailboat around Sardinia and Corsica and it was unforgettable! Every day, Bledar surprised us with new, freshly prepared culinary highlights - fresh, creative and prepared with a lot of love. He took care of us touchingly, left nothing to be desired and led us to the most beautiful bays, islands and snorkeling spots. We got to know wonderful people and thanks to his warm nature, everything felt like a vacation with friends. This week was the perfect mix of relaxation, adventure and enjoyment. It was the best holiday we have ever had. Thank you, dear Bledar, for this magical time! ❤️⛵️ Tuttepossible!
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/22/2025

Douglas B.

-

United Kingdom

An extraordinary experience that exceeded all expectations

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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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