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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

Wellness, sun, sea and adventure: a weekend full of sailing!

Italy: Tuscany

3 days - 2 nights

One departure available

September

€230

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

4 departures available

August - October

Starting from

€860

€774

Per person

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4.6

Capri, Ischia and Amalfi Coast by catamaran with hostess and cook

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€1,990

€1,791

Per person

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4.4

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

68 departures available

January - December

Starting from

€1,250

€1,125

Per person - min 2 pax

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4.8

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

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4.8

Super!

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€945

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

€950

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

Per person

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Reviews - Sailing or catamaran cruises with hostess or onboard cooking service

1514 reviews

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Maddalena Archipelago, southern Corsica: wonderful Sardinia

08/4/2026

Paola Z.

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IT

Massimo was without a sailor, in the week of mine and 2 other friends, which he knew the day before leaving. For us a hostess on board is a must. Consequent discussions then clarified through the requested intervention of sailsquare. Massimo has been corrected. No hard feelings between us, Some popular destinations, others too crowded. The boat would have everything but only one person in charge of everything, he cannot make it return. Well prepared kitchen. Improved breakfasts after clarification felt. Availability of Massimo if required what in his possibilities. Crossing with very rough seas, well managed by Massimo and fun. All in all we had a good time. I hope for him that help will arrive on board. We were all good..
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Aeolian Islands with hostess/cook BOAT 16.5 mt exclusive x6 people

08/4/2026

chiara s.

-

IT

The holiday you need! Spectacular landscapes, wonderful people, amazing cuisine! All surrounded by water, sun and wind! Congratulations on the passion and love you have for the boat, the kitchen and the life you live! You can feel everything! Unforgettable moments!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

08/4/2026

Lucia S.

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IT

Riccardo combines professionalism with sympathy. He is very patient and helpful and cooks really well.

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

08/4/2026

Assunta D.

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AU

Our sailing cruise with Alessandro was truly unforgettable! From exploring charming island villages and mooring in picturesque ports to diving straight into the warm, glorious sea, every moment was a highlight. Alessandro’s friendliness and cooking of local dishes made the experience even more special. Beyond being a fantastic host, he is an exceptionally skilled sailor with deep local knowledge of the Naples and Amalfi coast—and plenty of great stories to share. Experiencing these islands from the water offers a whole new perspective that you just can't get by land. We will definitely do this again.

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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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