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

3.7

Zakynthos sailing escape - 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

4.5

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

39 departures available

January - December

Starting from

€1,390

Per person - min 2 pax

cover image
avatar image

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

cover image
avatar image

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

€1,535

Per person - min 2 pax

cover image
avatar image

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

cover image
avatar image

4.3

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

Malta: Malta

6 days - 6 nights

7 departures available

August - October

Starting from

€690

Per person

cover image
avatar image

3.7

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

cover image
avatar image

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

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

4 departures available

September - October

€275

Per person

cover image
avatar image

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

cover image
avatar image

New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

26 departures available

August - September

Starting from

€170

Per person

cover image
avatar image

4.6

Ibiza e Formentera da S. Antoni a Eivissa

Spain: The Balearic Islands

6 days - 7 nights

One departure available

August - September

€1,200

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

1575 reviews

avatar image

A week sailing in the most beautiful places in the world

08/25/2026

Lucia D.

-

IT

Our review has special value because we traveled with our three-and-a-half-year-old daughter. Before leaving I was quite anxious, since it was our first experience on a boat; instead, it turned out to be one of the most beautiful holidays of our lives. Piero and Giusy were very affectionate with our little girl, involving her and making her immediately feel an active part of the crew. Thanks to the safety transmitted by Piero we never felt in danger, not even during a storm that turned into, on the contrary, the most magical moment of the trip. A special thanks goes to Giusy, an excellent cook: we ate great, you are special! Not at all trivial, we found everything very clean, from the kitchen to the dishes. For our part, we have tried to collaborate as best we can while respecting shared spaces and times. We had a really great time. We miss you so much, little Veronica and... I also believe in Coffee! 🤣
avatar image

Quattro giorni all'Elba - Hostess a bordo

08/25/2026

Carla F.

-

IT

I spent very pleasant and fun days, beyond my expectations. The boat is beautiful, well maintained and very clean and comfortable. The skipper is really an expert person and has made available to us not only his professionalism (we sailed) but also his sympathy. Giulia is a precise, helpful and helpful hostess. excellent cook. To this were added the travel companions with whom I shared big and fat laughs at all hours. Beautiful experience!!
avatar image

SARDINIA: discovering the wild South

08/25/2026

GIORGI C.

-

IT

It was a beautiful journey. Places full of beauty, very comfortable boat and excellent cuisine. Finally, super kind and nice Bianca and Paolo, A trip to be redone.

CORSICA NORD Paradise - catamaran cruise with hostess FULL BOARD

08/24/2026

Giulia P.

-

CH

Beautiful experience. Very nice boat and great staff

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