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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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4.6

"Boutique" sailing holiday from Athens to Hidra, Spetses and other pearls

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€1,200

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

5 departures available

August - September

Starting from

€723

€650

Per person

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3.0

Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

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4.5

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

11 departures available

October - December

Starting from

€1,430

Per person - min 2 pax

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4.3

Week on a 22m maxi-yacht between Pontine and Flegree

Italy: Pontine Islands

7 days - 6 nights

One departure available

August - September

€1,390

Per person

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4.5

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

25 departures available

January - December

Starting from

€1,600

€1,440

Per person - min 2 pax

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4.5

Premium

RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

11 departures available

January - December

Starting from

€2,330

Per person - min 2 pax

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3.0

Where the blue feels like home: the Ionian islands - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€779

Per person

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4.5

Premium

BORA BORA PARADISE - Mini catamaran cruise with hostess and full board

Pacific Ocean: French Polynesia

4 days - 4 nights

One departure available

October

Starting from

€2,305

Per person - min 2 pax

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New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

4 departures available

September - October

€275

Per person

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New

Premium

All inclusive sailing cruise on Dufour 54 sailboat in Croatia with hostess

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

August - September

Starting from

€1,830

Per person

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New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

28 departures available

August - September

Starting from

€170

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

1556 reviews

Five days in Croatia with skipper, instructor and cook

08/22/2026

riccardo f.

-

IT

Professional skipper who knows the area well, expert in fishing and as a cook, never intrusive. Trip a little conditioned by the scarcity of wind and the presence of jellyfish

Enjoy the Aeolian Islands with skipper and hostess

08/22/2026

Gabriele I.

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IT

Beautiful experience! Mauro and Betty made us feel immediately at ease. They know the islands perfectly and this allowed us to fully enjoy the experience, without having to think about anything. I absolutely recommend this experience to everyone! See you next time!

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

08/22/2026

Mario N.

-

IT

Summary of the 7 days spent together: crazy week! First experience on such a long boat for me and I must say I couldn't ask for anything better: to be done again immediately :) Mauro was super helpful (even on some really Mission Impossible requests!): good skipper and excellent cook! Mood of the crew: top! Beautiful people, beautiful stories, lots of laughter (and lots of aperitifs!) A special thanks also goes to Alissia: she helped Mauro in the daily routine and for us she was a magnificent storyteller, enchanting us with her adventures around the world! Pro tip: if you like live music, you've come to the right place! His guitar will keep you company on starry nights. And if you want to immerse yourself in the world of diving and freediving, Alissia will guide you :) Thank you guys and see you soon :) Fair winds! ⛵️
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Quattro giorni all'Elba - Hostess a bordo

08/21/2026

Andrea M.

-

IT

It was a beautiful holiday. Comfortable boat with private bathroom for each cabin. Comfortable outdoor spaces considering the complexities of the sailboat. Vittorio and Giulia were excellent hosts. Vittorio's experience and Giulia's kindness pampered us for the entire holiday.

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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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