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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

Sailing BenEssere in Ionian Greece

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,250

Per person

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4.4

Premium

TUSCANY Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Tuscany

7 days - 7 nights

One departure available

July - August

Starting from

€2,490

€1,990

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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4.4

Premium

KOH SAMUI Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

6 departures available

July - 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

Per person

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

Greece: Dodecanese

7 days - 7 nights

4 departures available

July - October

Starting from

€829

Per person

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4.4

Premium

TAHITI - RAIATEA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

12 departures available

January - December

Starting from

€2,330

€2,097

Per person - min 2 pax

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€1,785

€1,575

Per person

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5.0

Sailing adventures: summer sailing camps IN ENGLISH - for children from 9 to 14 years old

Italy: Tuscany

5 days - 5 nights

One departure available

July

€660

Per person

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5.0

Sail the Pacific: The Milky Way between Fiji and Vanuatu

Pacific Ocean: Fiji Islands

8 days - 8 nights

One departure available

July - August

€1,200

Per person

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5.0

Yoga, meditation and healthy eating in a natural paradise

Caribbean: San Blas Islands - Panama

5 days - 5 nights

4 departures available

July - August

€1,600

Per person

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New

Premium

All inclusive sailing cruise on Dufour 530 sailboat in Croatia with hostess

Croatia: Split Archipelago

7 days - 7 nights

3 departures available

August - September

Starting from

€1,645

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.

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

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

1462 reviews

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

07/17/2026

chiara s.

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IT

First experience on a sailing boat, three unforgettable days: sea, sun, absolute relaxation. Daniele Skipper prepared and competent, Mariapia delighted us with her fresh and delicious cuisine. Both made us fully savor the essence of sailing! Experience to be repeated!!
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2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

07/16/2026

Vincenzo T.

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IT

Weekend spent relaxing and having fun, we found a beautiful sea and thanks to Fabrizio's advice we fully enjoyed the boat and discovered beautiful places to swim safely with my family. It was definitely a wonderful experience.

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

07/14/2026

daria d.

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IT

"Sea force Aeolian" Sailing with Andrea means feeling constantly in safe hands. His great experience and professionalism have emerged in every single detail. Always attentive and precise, prepared on the routes and a profound connoisseur of the secrets of the islands, he was able to make us experience a literally unforgettable week. The sunsets, the sea, the sea-based lunches and dinners on board that would be the envy of the best restaurants, the comfort of the catamaran and the perfect synergy between Andrea and Arianna created a special atmosphere on board. Pure magic. Thank you for everything!
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2026

Stefano M.

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IT

Riccardo is a wonderful person, he fully infuses all his innate passion for the sea, nature and sailing. Excellent teacher, if interested he allows you to participate in the maneuvers of the boat explaining each step perfectly. Wonderful proposed itinerary, excellent cook who manages to satisfy all the dietary needs of his guests. Helpful and with excellent organizational skills.

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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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