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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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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

September - October

Starting from

€1,100

Per person

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New

Premium

All inclusive sailing cruise on Excess 11 Catamaran in Croatia with hostess

Croatia: Split Archipelago

7 days - 7 nights

One departure available

September

Starting from

€1,965

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

5 departures available

September - October

Starting from

€690

Per person

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New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€275

Per person

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New

Four days of relaxation midweek on the island of Elba with hostess

Italy: Tuscany

4 days - 3 nights

2 departures available

September

€424

Per person

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4.8

New

Cruise in southern Sardinia: charm and turquoise waters in schooner with hostess and full board

Italy: Southern Sardinia

6 days - 6 nights

2 departures available

September

Starting from

€1,200

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

2 departures available

September

€215

Per person

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4.4

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

One departure available

October

Starting from

€1,485

Per person - min 2 pax

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4.4

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

53 departures available

January - December

Starting from

€1,270

€1,143

Per person - min 2 pax

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4.4

Premium

BAHAMAS EXUMA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

6 days - 7 nights

50 departures available

January - December

Starting from

€1,815

€1,634

Per person - min 2 pax

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New

Premium

All inclusive sailing cruise on Lagoon42 Catamaran in Croatia

Croatia: Split Archipelago

7 days - 7 nights

One departure available

September

Starting from

€2,150

Per person

Why book a holiday with Sailsquare?

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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

1630 reviews

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

09/10/2026

Alice M.

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IT

Overall nice holiday but with some critical aspects. Initially the catamaran was not of the model confirmed for our trip, in fact our cabin had a shower without the glass cover so it flooded everything every day and there were no shutters for light on the windows. The sore point was the skipper, who did not meet the needs at all to make the group feel good. The first day before departure he told us the meal times (breakfast at 8 am, lunch at 1 pm and dinner at 7 pm), which immediately created general discontent. On vacation and especially with temperatures in August, thinking about respecting these holiday schedules becomes a nightmare. Although I pointed out, the answers on everything from the skipper were negative, so much so that I went so far as to shout in my husband's face for a trifle. Nothing was explained to us when we arrived on the islands and often to find a place in the ports we were forced to leave very early. Itinerary not with the sea that I would have expected. As for the hostess, on the other hand, she was very good and very attentive to our needs.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/9/2026

Parmentier S.

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BE

We had a very pleasant time, a very nice captain and hostess, a super nice doggie, a very nice boat, wonderful weather and blue everywhere, the dream.

Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/9/2026

Vincenzo F.

-

IT

Fantastic week. Perfect organization, hospitality and kindness are guaranteed. Giorgio and Diego excellent "hosts".
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Aeolian Islands on a catamaran, professional skipper/hostess, what else?

09/8/2026

Stefania P.

A week on a catamaran in the Aeolian Islands that I will hardly forget! ⛵️🌊 Andrea, our skipper, and Arianna, our hostess, were just amazing. Andrea is a real guarantee: competent, quiet and solid, he knows the Aeolian Islands and their sea like the back of his hand. He took us to discover wonderful places making us feel always in excellent hands. Arianna was very attentive to everything and everyone, always present and available. It was enough for someone to pronounce the word "beer?" and Arianna had already uncorked and made cheese, olives and taralli appear. They definitely spoiled us even at the table: delicious fish, pasta, vegetables, salads, wine... We really didn't miss anything. We discovered the Aeolian Islands from a wonderful perspective: during the day from the sea, between bays, dives and incredible views, and in the evening going ashore for a walk, a granita or an aperitif. One of the moments that I will definitely take with me is Stromboli: the sea crossing at sunset and the spectacle of the Sciara del Fuoco seen from the catamaran were exciting and evocative, difficult to describe in words. To make this holiday even more special was also the group I was lucky enough to find. People who a week earlier were strangers and with whom, between laughter, life on a boat, aperitifs and shared moments, a beautiful understanding was created. I left for a week in the Aeolian Islands and came back with many more memories than I thought I would pack. ❤️ Thank you Andrea, Arianna and the whole group for making this experience so special. I would do it again tomorrow! Greetings from Paris 😉

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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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