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

4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

11 departures available

August - November

Starting from

€1,640

€1,558

Per person - min 2 pax

cover image
avatar image

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

July - October

Starting from

€1,200

€1,080

Per person

cover image
avatar image

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - October

Starting from

€590

Per person

cover image
avatar image

4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

8 departures available

August - October

Starting from

€2,500

€2,250

Per person

cover image
avatar image

5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

cover image
avatar image

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€1,150

€1,035

Per person

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

11 departures available

August - October

Starting from

€570

Per person

cover image
avatar image

4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

Per person

cover image
avatar image

4.8

Super!

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

July - August

Starting from

€1,150

Per person

cover image
avatar image

New

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

Italy: Southern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,200

Per person

cover image
avatar image

5.0

Super!

Ionian Greece aboard a Catamaran with Skipper/Chef

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,900

Per person

cover image
avatar image

4.8

Super!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

2 departures available

August - September

Starting from

€1,100

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

1461 reviews

avatar image

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

07/16/2026

Vincenzo T.

-

IT

Weekend spent relaxing and having fun, we found a beautiful sea and thanks to Fabrizio's advice we fully enjoyed the boat and discovered beautiful places to swim safely with my family. It was definitely a wonderful experience.

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

07/14/2026

daria d.

-

IT

"Sea force Aeolian" Sailing with Andrea means feeling constantly in safe hands. His great experience and professionalism have emerged in every single detail. Always attentive and precise, prepared on the routes and a profound connoisseur of the secrets of the islands, he was able to make us experience a literally unforgettable week. The sunsets, the sea, the sea-based lunches and dinners on board that would be the envy of the best restaurants, the comfort of the catamaran and the perfect synergy between Andrea and Arianna created a special atmosphere on board. Pure magic. Thank you for everything!
avatar image

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2026

Stefano M.

-

IT

Riccardo is a wonderful person, he fully infuses all his innate passion for the sea, nature and sailing. Excellent teacher, if interested he allows you to participate in the maneuvers of the boat explaining each step perfectly. Wonderful proposed itinerary, excellent cook who manages to satisfy all the dietary needs of his guests. Helpful and with excellent organizational skills.

Maddalena Archipelago, southern Corsica: wonderful Sardinia

07/14/2026

Andrea C.

-

CH

We have just returned and we are already homesick! It was a beautiful week, between crystal clear waters, wonderful coves, sailing and views that we will hardly forget. Massimo is an experienced skipper who always makes you feel in good hands and chooses the best route based on the sea and the wind, also taking you to truly special places. Martina was welcoming and pampered us all week with really good lunches, dinners and aperitifs. To make the holiday even more special were the company and the many laughs with our travel companions Anthony and Sergio: in a few days a beautiful atmosphere was created, as if we had known each other forever. Even our son Noah, 9 years old, at his first experience on a sailing boat had a lot of fun and Massimo had many small attentions for him that made him live this adventure with enthusiasm and serenity. The boat is comfortable, well maintained and the atmosphere that was created on board made everything even more beautiful. One of those holidays that end too quickly and that immediately make you want to leave again. Thank you Massimo, Martina and the whole crew for this wonderful week, we will carry this experience in our hearts! Andrea, Fabiola and Noah

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