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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!

From Santorini to Milos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

July - August

€1,050

Per person

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5.0

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

Greece: Ionian Islands

7 days - 7 nights

31 departures available

March - October

Starting from

€460

Per person

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4.3

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

32 departures available

February - December

Starting from

€1,680

€1,512

Per person - min 2 pax

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4.3

Premium

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

38 departures available

January - December

Starting from

€1,125

€1,013

Per person - min 2 pax

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4.3

Premium

TAHITI - RAIATEA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

21 departures available

January - December

Starting from

€2,330

€2,097

Per person - min 2 pax

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4.8

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

€1,100

Per person

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4.3

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

25 departures available

May - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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5.0

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

Italy: Tuscany

3 days - 3 nights

16 departures available

April - October

Starting from

€350

Per person

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4.8

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

June - August

Starting from

€1,150

Per person

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4.9

10 EPIC DAYS: From the Dodecanese to Milos with Hostess on board

Greece: Cyclades

8 days - 9 nights

One departure available

August

€1,430

Per person

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4.3

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

20 departures available

May - October

Starting from

€1,525

€1,373

Per person - min 2 pax

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4.8

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

5 departures available

July - September

€1,150

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

1374 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/26/2026

Sabrina B.

-

Italy

Fantastic experience and very qualified staff. Maybe I thought I would see more beaches but in general I was very satisfied.
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/19/2026

Elena B.

-

Italy

Amazing experience! Skipper (Medhi) and Cook (Kris) super capable smart and funny ♥️
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

01/17/2026

Paola C.

-

Italy

Very nice experience overall the only thing for the destination maybe it is better to do more days as the last three days we did too much sailing in the afternoon, it would have been better to travel at night / early morning or possibly do more days in the Tobago cas area, Skipper very nice and quiet, the steward perhaps a little too young did not have a great desire to clean and lacked the eye of a person with more experience. Overall I would do it again
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Wellness Adventure Retreat

01/14/2026

Donna S.

-

Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!

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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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