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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

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

4 departures available

July - September

€1,150

Per person

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New

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

Italy: Southern Sardinia

6 days - 6 nights

22 departures available

April - September

Starting from

€900

Per person

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4.5

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

8 departures available

June - October

Starting from

€1,485

Per person - min 2 pax

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5.0

Sailing BenEssere in Ionian Greece

Greece: Ionian Islands

7 days - 7 nights

3 departures available

June - August

€1,250

Per person

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New

Discover both the Dodecanese and Cyclades, Leros to Santorini and back

Greece: Cyclades

11 days - 11 nights

One departure available

September

€2,495

Per person

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4.5

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

27 departures available

April - December

Starting from

€1,125

€1,013

Per person - min 2 pax

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4.5

Premium

TUSCANY Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€2,390

Per person - min 2 pax

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5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Italy: Southern Sardinia

3 days - 2 nights

6 departures available

May - September

€690

€621

Per person

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4.9

The Alternative to the Catamaran From Elafonissos to Athens

Greece: Peloponnese

7 days - 7 nights

One departure available

May

€590

Per person

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4.5

Premium

KOH SAMUI Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

17 departures available

May - September

Starting from

€1,785

€1,339

Per person - min 2 pax

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4.6

Discover the most authentic Greece from Samos to Arki and Agathonisi, with skipper and chef

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,200

€1,080

Per person

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Aegean dreams: sailing around Rhodes - hostess on board (half board)

Greece: Dodecanese

7 days - 7 nights

12 departures available

May - October

Starting from

€829

€746

Per person

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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

1404 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

04/16/2026

DONATELLA D.

-

Italy

My rating is just enough and I would actually only give it 2 stars. Unfortunately the holiday turned out to be far below expectations, the quality / price ratio is very bad. First of all, the French skipper who speaks almost no English is unacceptable with a group of guests from various nationalities. In case of emergency, the captain must know how to give clear and quick orders and he would not have been able at all. The French hostess (his girlfriend) cooked everything except "navigation" food: for the whole holiday as vegetables only two salad leaves and one evening green beans, in the first three days there was practically no fruit and in the tropics it is a must, fish eaten only twice and meat after all; he always cooked heavy lunches / dinners that did not go well with the environment and the temperature ... The answers to the various intolerances or requests for vegetarian dishes were rude and considered only sometimes. The group we sailed with fortunately turned out to be the trump card of the holiday, we were all on the same wavelength and complained about the same things. Our collective requests to stay a little longer in one place or to change times for activities have never been answered in the affirmative, revealing an excessive rigidity on the program and on the needs of the captain-hostess as a couple. Another sore point is navigation: 13 hours at night as soon as you embark and then immediately "segregated" in the cabin with the order not to leave until 6 in the morning is madness. In our group two people were sick, one of whom was in a single cabin and neither the hostess nor the captain bothered to go and check on her and give her a hand in case of need. Unfortunately, even the places visited are below expectations: obviously they are beautiful places, but as far as coral reefs and marine fauna are concerned, they are very lacking. They made us do 2-3 snorkeling in very busy places (a little bit for a week on the boat). The cleanliness left a bit to be desired and note that the cabin has to be cleaned by itself throughout the week. Basically I loved the catamaran and the holiday at sea but there were too many poor points so in the future I will definitely evaluate other destinations and modalities.
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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

04/3/2026

gulce c.

-

Türkiye

It was wonderful, thank you !
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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

03/31/2026

Roberto C.

-

Italy

An unforgettable experience thanks also to the whole team, both organizational and on the boat. Highly recommended tour, perhaps to be tackled with a few more days on the boat to avoid long crossings back.
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Four days in the paradise of the San Blas Islands - All inclusive

02/26/2026

Gianluca A.

-

United States

Luigina and Alessandro made us feel at home since the very first moment. They cooked incredible meals, were always attentive to our needs, and we truly enjoyed spending time with them. It was probably one of our best family sailing adventures. On top of that they made us discover the San Blas islands: crystal clear water, white sand beaches, snorkeling, paddle boarding and of course sailing between the islands. So much to do and a joy doing it with them especially thanks to their deep knowledge of the are. Definitely highly recommended!!

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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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