header cover
sailsquare logo

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

4.3

Premium

BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

55 departures available

January - December

Starting from

€1,250

€1,125

Per person

cover image
avatar image
Discover the Egadi Islands on a sailboat with aperitif and hostess on board!

Italy: Aegadian islands

1 day - 0 nights

86 departures available

July - September

Starting from

€130

€117

Per person

cover image
avatar image

4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

10 departures available

July - October

Starting from

€1,260

Per person - min 2 pax

cover image
avatar image

5.0

Cruise between Sardinia and Corsica with hostess

Italy: Northern Sardinia

7 days - 7 nights

One departure available

July

€1,250

Per person

cover image
avatar image

5.0

10-Day All Inclusive Ibiza & Formentera Cruise - with Hostess

Spain: The Balearic Islands

10 days - 9 nights

6 departures available

July - October

Starting from

€2,000

Per person

cover image
avatar image

4.3

Premium

CORSICA SUD Dream - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

13 departures available

June - October

Starting from

€1,485

€1,337

Per person - min 2 pax

cover image
avatar image
Sun, sea and relaxation... Discovering the Aeolian Islands - with Hostess

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

July

€1,260

Per person

cover image
avatar image

4.3

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Guadeloupe

6 days - 7 nights

57 departures available

January - December

Starting from

€1,125

€1,013

Per person

cover image
avatar image

4.3

Premium

EXUMA Dream Premium - 8 days in Catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Bahamas

6 days - 7 nights

10 departures available

July - December

Starting from

€1,865

Per person

cover image
avatar image

4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€2,100

€1,995

Per person

cover image
avatar image

4.9

Argentario, Giglio and Giannutri Week - Hostess on board

Italy: Tuscany

6 days - 7 nights

One departure available

July

€1,060

Per person

cover image
avatar image

4.9

From the Lighthouse to the Volcano: sailing from Gibraltar to Lanzarote by catamaran

Spain: Andalusia

7 days - 7 nights

One departure available

November

€1,300

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

1167 reviews

avatar image

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

06/30/2025

Gilberto B.

-

Italy

Alessandro, Carlo, Andrea e Marta sono andati oltre ogni possibile aspettativa regalandoci una settimane di relax, incantevoli spot nello ionico, deliziosi pranzi a bordo e fuori. Abbiamo trovato disponibilità, sensibilità e accoglienza fuori dal comune. Barca pulita, ottima comunicazione e organizzazione. Nessun dettaglio lasciato al caso, una vacanza indimenticabile!
avatar image

Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

06/30/2025

Beatrice S.

-

Spain

No se podía esperar más de un viaje. El catamarán grande y nuevo. A/C siempre que hacía falta y agua en abundancia. El Capitán Lutius no podía ser más profesional y simpático. Nos hizo sentir a todos cómodos y siempre proponiendo hacer diferentes actividades en un ambiente divertido y desenfadado. Karin, la chef igualmente agradable y divertida. Muy profesional y atenta a nuestras necesidades. Los lugares que visitamos de ensueño y a pesar de algunas lluvias en línea general ha merecido la pena navegar fuera de temporada al estar prácticamente solos en los sitios más alucinantes. Siempre hemos tenido suerte con el resto de los clientes y en este caso no ha sido diferente y a pesar de ser mayoritariamente de habla francesa nos hemos comunicado muy bien en inglés.
avatar image

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

06/30/2025

Alessandra M.

-

France

É stata un’esperienza unica, la barca é il modo migliore per visitare le bellissime Eolie. E che barca: un catamarano grande e moderno, con uno skipper esperto ed affidabile affiancato da una bravissima cuoca. L’atmosfera a bordo era perfetta, con il mix ideale di relax e divertimento. Non sono mancate escursioni a terra (trekking su Vulcano e visite ai bellissimi paesi isolani, anche solo per mangiare una granita), nuotate in luoghi segreti meravigliosi, notti in rade silenziose, serate nei locali a terra, aperitivi guardando il tramonto in mezzo al mare… davvero la vacanza perfetta per chi vuole godersi le isole.
avatar image

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

06/30/2025

Damien D.

Amazing sailing trip. The itinerary was great, the Skipper super nice and the boat very comfortable. excellent stewardess and the food on board was delicious. we are looking forward for the next trip with Maurizio !

Customer Support

nightLifeGeneralInfo

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!

search

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