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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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4.5

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

One departure available

October

Starting from

€1,320

€1,056

Per person - min 2 pax

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New

Just relaxing while sailing on the Côte d'Azur

France: French Riviera and Porquerolles

2 days - 2 nights

5 departures available

August - October

Starting from

€450

€405

Per person

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4.5

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

August - October

Starting from

€1,305

€1,044

Per person - min 2 pax

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5.0

New

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

Italy: Southern Sardinia

6 days - 6 nights

5 departures available

August - September

Starting from

€1,200

Per person

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4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€1,000

€850

Per person

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4.5

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GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

45 departures available

January - December

Starting from

€1,680

€1,260

Per person - min 2 pax

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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

2 departures available

August - September

Starting from

€1,924

Per person

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New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

35 departures available

August - September

Starting from

€170

Per person

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4.5

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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

43 departures available

January - December

Starting from

€1,310

€1,179

Per person - min 2 pax

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4.5

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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

8 departures available

August - October

€1,250

Per person

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4.5

Premium

DALMATIAN Paradise - Catamaran cruise with hostess FULL BOARD

Croatia: Split Archipelago

7 days - 7 nights

One departure available

August

Starting from

€2,000

€1,800

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

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

1547 reviews

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Elba a sea of emotions - Hostess on board (3 cabins and 3 bathrooms)

08/17/2026

Gabriele P.

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IT

We spent unforgettable days with a great time and excellent company and many stories of experiences lived. Fabio and Angela hosted us at their home and did not let us miss anything. Sailing upwind with [hidden] inclined gave us wonderful emotions that I recommend everyone to try. In addition to demonstrating great sailing experience, the captain is super helpful, a great guide and super attentive to the millions of comments from the crew.

Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/17/2026

giulia c.

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IT

A truly beautiful holiday and an experience that I will take with me! Corfu, Paxos and Antipaxos are wonderful places, with a spectacular sea and landscapes that can be experienced by boat in an even more special way. The travel companions were also great and helped make this week even more enjoyable. A special thanks to Alessandro, our skipper, always available and attentive to the needs of the group. Before boarding there were some small communication and organization problems, but Alessandro was willing to find a solution and meet the needs. A special thanks also to Carlo, our steward, a really kind, discreet and helpful person, always ready to respond to any need and make life on board more enjoyable. Overall it was a truly memorable holiday, made up of beautiful sea, beautiful places, laughter, beautiful people and many emotions. I would definitely do it again!

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

08/17/2026

Prash S.

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FR

We had one of our most memorable weeks exploring the Amalfi Coast with Alessandro and a group of wonderful strangers (now friends). Alessandro was very thoughtful and produced a great and varied programme and social experience. The whole experience felt special and authentic. I wish all weeks were as enjoyable as this ! The worst part was when it ended ! Highly recommended !
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All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

08/17/2026

MANUELA B.

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IT

A wonderful week to discover the Amalfi Coast, experienced from a very special perspective: the sea. ⛵️💙 The sailboat is comfortable, functional and welcoming, and allowed us to fully enjoy every moment of the holiday. The Amalfi Coast is simply spectacular, a beautiful sea, unique landscapes and cities full of charm, all to be discovered. A special thanks goes to the captain, Alessandro, always kind, helpful and attentive to our needs. In addition to being an excellent captain, competent and able to handle any event during navigation with tranquility, he also turned out to be a very good cook! 😊 He made us feel at ease and accompanied us in this experience with sympathy and professionalism. And then Naples... It is impossible not to fall in love with its atmosphere and especially with its food, really delicious! ❤️ It was a beautiful holiday, made up of sea, wonderful places, good food and beautiful people. An experience that I will remember with great affection. Thank you so much for this wonderful week! ⛵️☀️🌊

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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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