header cover
logo

Log in

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.

cover image
avatar image

4.4

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

40 departures available

January - December

Starting from

€1,430

€1,144

Per person - min 2 pax

cover image
avatar image

4.4

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

73 departures available

January - December

Starting from

€1,535

€1,228

Per person - min 2 pax

cover image
avatar image

4.4

Premium

RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

28 departures available

January - December

Starting from

€2,330

€1,864

Per person - min 2 pax

cover image
avatar image

4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

3 departures available

September - October

€690

Per person

cover image
avatar image

4.2

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

cover image
avatar image

4.4

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

cover image
avatar image

New

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

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€275

Per person

cover image
avatar image

New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

34 departures available

September - October

Starting from

€150

Per person

cover image
avatar image

5.0

A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

8 departures available

October - December

Starting from

€1,925

€1,733

Per person

cover image
avatar image

4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

October

€740

Per person

cover image
avatar image

4.2

Sailing the Aegean: a Greek Islands escape - hostess on board (half board)

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

Starting from

€929

Per person

cover image
avatar image

5.0

New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

5 departures available

September - October

Starting from

€1,200

€500

Per person

Why book a holiday with Sailsquare?

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

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

1657 reviews

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/22/2026

Paolo C.

-

IT

The wonderful places visited certainly do not need approval but certainly the added value of this experience were Fabrizio and Monica. Two people who were always smiling and helpful who allowed us to live a week difficult to forget but above all thanks to them we really 'disconnected' from a long and difficult work routine. Fabrizio, our captain, a welcoming guy and always available. Monica welcomed us every morning with a smile and a thousand delicious dishes. Really two people out of the routine and therefore absolutely exceptional. Thank you very much

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/22/2026

Marcella L.

-

IT

I spent a wonderful week on board the catamaran discovering the Aeolian Islands together with a group of great people! It was the perfect choice to experience this archipelago to the fullest. Every day a different emotion and spectacular bays in which to wake up. A special thanks to Fabrizio, who with great professionalism and sympathy guided us to the best moorings, always anticipating the weather and to Monica the Super Hostess who pampered us throughout the week with her desserts and excellent cuisine. 100% recommended holiday

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

09/22/2026

Birgit H.

-

DE

What a great trip! Seen a lot! Ate a lot! Beautiful coves where you can anchor and admire the sunset with an aperitivo. Bledar is a very responsible skipper, very helpful and always attentive to the wishes of his guests. He makes several suggestions every day and knows the most beautiful corners. And his cooking skills are excellent too! It's just a pity that there was too little wind to sail!

Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/21/2026

Pierluigi O.

-

IT

Spectacular catamaran. Well structured itinerary. A truly unforgettable experience in the Aeolian Islands! The catamaran was the perfect way to experience the sea, but what really made the difference was the professionalism and passion of the skipper and cook on board. Angelo, the skipper, proved to be a true sea dog: a great connoisseur of the islands, always attentive to the conditions of the sea and the needs of all of us. He took us to wonderful bays and coves, making us discover spectacular corners and making every navigation pleasant and safe. His experience and tranquility allowed us to enjoy every moment without worries. And then the cook, Diego, a real surprise! Every day he delighted us with delicious dishes, well-kept and rich in flavors, enhancing the specialties and products of the territory. Eating on board, with the Aeolian sea in front of our eyes, was one of the best moments of the holiday. A professional couple who, with competence, availability and sympathy, made the trip even more special. An experience that I absolutely recommend and that I would do again without hesitation!

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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

.

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.

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964