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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!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

One departure available

July

€790

Per person

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4.8

Super!

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

August

€1,115

Per person

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5.0

Super!

A fantastic day on a boat in the blue sea of Tuscany

Italy: Tuscany

1 day - 0 nights

27 departures available

August

€145

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

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4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Karpathos

Greece: Dodecanese

7 days - 6 nights

One departure available

September - October

€950

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.8

Super!

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

July - September

Starting from

€1,385

€1,316

Per person

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4.8

Super!

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Italy: Naples & Amalfi Coast

3 days - 2 nights

24 departures available

July - October

Starting from

€1,325

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

1189 reviews

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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2025

Alberto M.

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Italy

Riccardo proved to be an excellent Skipper, a true professional, always ready to take advantage of any gust of wind to unfurl the sails. Great cook and great company. A boat experience with Riccardo is highly recommended.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/14/2025

Claudia Z.

-

Italy

Seven days, one boat, a thousand emotions We spent a wonderful week on a sailing boat exploring the beauties of Corfu and the nearby islands, guided by a skipper who was truly out of the ordinary: Andrea. It is evident that he deeply loves his job – competent, professional, capable of transmitting confidence and serenity even when the weather has decided to throw a tantrum. Two days of forced stop in port could have ruined the spirit of the trip, but Andrea was able to turn everything into an opportunity to discover, learn and relax. Always ready with a kind word, interesting information or a joke at the right time, he did much more than you would expect from a skipper, including top info about the restaurants! Also on board with us was Carlo, a discreet and attentive steward, who with his caring presence made life on board even more comfortable. The boat, spacious and comfortable, was our perfect floating retreat. And Mattias, the poodle on board? A sweet cuddle that conquered everyone, including the most insensitive to hairy faces. An added value was the proximity of the boat of Andrea's brother, Alessandro: this allowed us to get to know the participants of his boat and to share very pleasant moments together, including aperitifs, laughter and chats under the stars. If I really have to find a point on which to suggest an improvement but it is a constructive personal thought: it is the kitchen. With a little more focus on variety, ingredient quality, and presentation, the experience could really level up. Because, let's face it, customers are often won over even with just a well-thought-out dish! That said, it was a holiday full of excitement, beautiful scenery and great company. We would gladly do it again and I will over-recommend it to friends at home – maybe without wind, but always with Andrea at the helm!
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Aeolian Islands: wellness, taste, fun with fabulous cook on board

07/14/2025

Gisella P.

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Italy

Exceptional welcome, competence, availability and empathy!
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The alternative to the catamaran in the Sporades

07/14/2025

Pietro M.

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Italy

The sailing experience with Manuele was magical. He is a formidable captain, attentive to everything around him, always transmitting confidence and passion in everything he does. An exceptional chef who surprises you every day with his dishes. Being able to share this experience with him was a privilege that I wish for everyone. He made me fall in love with sailing, I will definitely come back with him for more adventures.

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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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